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Private Introduction to Old San Juan Sightseeing Driving Tour - 1 Hour

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Old San Juan Tours

Discover old san juan on tours led by locals.

Discover the charm and history of Old San Juan, the oldest city in the United States, with MBTION VIP’s convenient driving tours! Leave behind the sweat and physical exertion as you explore the cobblestone streets and iconic landmarks comfortably seated in your own air-conditioned vehicle. Knowledgeable guides, who are also historians, will share fascinating stories about The Capitol Building, The Presidents Walkway, San Geronimo, El Morro, San Cristobal, San Jose Chapel, Colombus Square, Ponce de Leon Square, La Perla, and many more ensuring you don’t miss a single detail.

Choose from our range of Old San Juan tours and let MBTION VIP be your host in uncovering the wonders of this treasured Puerto Rican city! Book online today.

• Most Popular!
• Old San Juan Tour
• Clock 1, 2, 3, 4 & 5 Hours
• User For All Ages

1-Hr, 2-Hr, 3-Hr, 4-Hr & 5-Hr Old San Juan Tour

Comfortably explore Old San Juan on a tour in our AC-cooled vehicle! Avoid searching and sweating under the hot tropical sun and enjoy the 10-minute stops for capturing unforgettable memories. Book online today!

• Clock 4 Hours

Private 4-Hr Old San Juan Tour & Piñones Package

Old San Juan and Piñones, Loiza all in one! Go through Puerto Rico’s African Heritage and taste famous authentic Afro-Puerto Rican street food in this 4-Hour Tour.

• Old San Juan Tour , Nature & Rainforest Tour
• Clock 6 Hours

Private 6-Hr Old San Juan Tour & El Yunque National Forest Angelito Trail Package

Uncover the rich heritage and natural wonders of Puerto Rico by experience the captivating Old San Juan and the breathtaking beauty of El Yunque National Forest through this tour!

• Clock 9 Hours

Ultimate San Juan Discovery - Private Full Day Experience

Visit America’s oldest city, Old San Juan, Santurce! In this full day tour you will get to experience history, landmarks, art, rum tasting, Afro-Puerto Rican culture, and end it at the beach.

• Clock 3 Days

Private 3 Day Puerto Rico Discovery Package

Experience Puerto Rico in three days off the beaten path with a package offering the best beach, history, and nature lovers experience! Discover Puerto Rico’s hidden gems. Book online today!

Private San Juan Driving Tour

Quick Details

• Hour Glass Duration: 2.5 hours
• Users Capacity: 1-6 people

Private Introduction to the City of San Juan

Enjoy a personal and private 2.5 hour introduction to the City of San Juan, the second-oldest European-founded settlement in the Americas and the oldest under US jurisdiction.

• The first 4 passengers are included in the base price, but each passenger beyond that will have an additional fee of $25 per person.
• Children 5 years and younger are free but must use a car seat/booster seat.

Experience the must-see highlights of San Juan on this guided, sightseeing driving tour. Ride in style through the Old City neighborhood in Old San Juan, near the San Cristobal and San Felipe del Morro Forts. Visit the 1# hotel in Puerto Rico by Tripadvisor, El Convento Hotel. Stop for a photo at the world-famous Presidential Boardwalk to take a photo with your favorite president, or a run up the Steps at the Capital Building.

These are some of the Districts of San Juan we may visit. Old San Juan – the historic part of the city, home to most historic architecture, attractions, and galleries.

International Convention Center District – home of Puerto Rico’s biggest convention center. Brand new entertainment venue includes restaurants, shopping, cinema, urban Zipline, hotels and music hall.

Santurce – a historical part of San Juan known for its art and culture, having two art museums, a performing arts center and its famous marketplace.

El Condado – this upscale residential neighborhood is also the beach resort part of the city and has many hotels and restaurants along its main thoroughfare, Ashford Ave.

Isla Verde – Isla Verde is actually located in the adjacent municipality of Carolina, within the larger metro area. It is closest to the international airport and has nice beaches, hotels and parks.

Piñones – popular area in the town of Loiza, known for it’s typical fritters, Puerto Rican cuisine and seafood; and culturally, where our stronger African heritage lays.

Please Note:

• If traveling with children from 0 – 6 years a car seat/ booster seat is required. Please notify at the moment of booking if you will be traveling with your own or require us to provide it. We provide them complimentary, but need to be requested with anticipation.
• Food & beverage costs not included
• Rush hour/traffic may be encountered at certain times of a day
• Transportation included from any San Juan location

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If you want to experience the culture and the gastronomy of Puerto Rico, nothing is better than making a trip to Guavate! Enjoy traditional dishes like: roast pork, BBQ ribs, rice and beans, “pasteles”, pavochón, Puerto Rican sweets and “piña colada”.

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Old San Juan Historical Tour

Get to know Old San Juan’s history and sights on this walking tour of the city, including the San Juan Gate, El Convento Hotel, and La Casa Blanca.

Travel, Hiking, Food

One Day in Colorful Old San Juan Itinerary: What to See and Eat in Old San Juan

Have one day in old san juan and wondering what are the best things to do there this old san juan itinerary not only shows you the cool things to do in the colorful old san juan but also where to eat, park your car and other useful tips..

This blog contains occasional affiliate links, where I receive a small commission on sales of the products/hotels that are linked at no additional cost to you. In addition, as an Amazon Associate, I earn from qualifying purchases.

Old San Juan is a charming historical town in Puerto Rico. It is one of the most popular places for travelers and even cruise liners to visit when vacationing in Puerto Rico.

From historical forts to rainbow colored houses to beautiful murals to delicious restaurants, Old San Juan is a must do for anyone visiting Puerto Rico.

One day in Old San Juan is perfect for exploring this historical district, understanding its history, doing some shopping (real shopping and souvenir shopping), grabbing a drink and getting some nice photos.

Read on for my super practical guide on how to spend a day in Old San Juan. This guide is kids friendly too and I’ll give you some good tips!

Summary of One Day Old San Juan itinerary

If you are short on time and just want to see a brief summary, here is my super condensed mini guide on the best way to spend a day in Old San Juan. This itinerary assumes you start your day at 9am to maximize your time there.

9am: Arrive and grab a quick coffee/ pastry 9:30am: Explore the colorful streets of Old San Juan and find the best photo spots 10:30am: Visit Castillo San Felipe del Morro 12pm: Cuartel de Ballajá 1pm: Lunch in Old San Juan 2:30pm: Explore more and do some shopping and visit more photo spots 4:30pm: Bar hopping and dinner in Old San Juan or Condado

General Travel Information For Old San Juan

• Currency : US dollars
• Language : Spanish (main language) and English (Old San Juan is touristy so people speak English)
• Payments : Credit Card works perfectly
• Best Navigation : Google Maps
• Best Way to Get Around : Walking

How to Get to Old San Juan

If you are not staying in Old San Juan, you will need to commute in from your hotel early in the morning.

There are several different ways to get to Old San Juan, depending on your budget.

Uber is an easy way for those who do not want to drive. You can get an Uber easily in San Juan, whether you are staying in Condado or Isla Verde.

Taxis can be found outside of hotels and touristy spots as well. If you don’t know how to take an an Uber. Your hotel can also help you book a taxi.

An easy way to get to Old San Juan from other parts of Puerto Rico is to drive yourself . There are a number of great parking lots in Old San Juan. For more details on driving to Old San Juan, see my driving in Puerto Rico post.

Lastly, you can always take a public bus to Old San Juan. I didn’t take a bus in San Juan but I read it’s not always on time and can be inconvenient, but it is the cheapest option to get around.

Best Tours for Old San Juan

While you can totally do a self guided walking tour of Old San Juan, if you are the type that wants to learn more about what you are looking at or you do not like to plan, it may be better for you to take a tour or two in Old San Juan.

There are two tours I would highly recommend for anyone wanting a guide in Old San Juan:

• Old San Juan Historical Walking Tour (or this one ) is a 2 hour guided tour that shows you some of the most important buildings and churches in Old San Juan (and their historical background). You will also see some of the most colorful streets in San Juan with this tour.
• Old San Juan Food Tour (includes food) is the perfect tour for those that want to try local cuisine and drinks. There are a ton of restaurants in Old San Juan, with this food tour you don’t have to worry about going to the wrong places, since food tours always take you to the best local places to eat. I will mention some of these restaurants later in this Old San Juan blog post.
• Old San Juan Barcrawl (includes alcohol) is an evening guided tour that takes you around the best bars in Old San Juan. You will stop by at least 3 bars with your guide with shots and local drinks included. You can also meet other fun people on this tour, making this the perfect way to end your evening in Old San Juan.

Map of Old San Juan

Below is the map of Old San Juan with the main activities book marked. I always like to have a visual map of where attractions are so I can group things together to save time. On the map of Old San Juan below, I also added restaurants and bars that I recommend so you have everything in one place!

Black pins : what to see in Old San Juan (including photo spots) Blue pins : restaurants to eat in Old San Juan Purple pins : bars in Old San Juan Orange pins : Coffee shops and breakfast spots in Old San Juan Red pins : best ice cream shops in Old San Juan

Detailed Colorful Old San Juan Itinerary for 1 Day

This super detailed Old San Juan itinerary aims to maximize your time there while providing practical tips (like expect long lunches because they have a slower pace).

Since this is a sample Old San Juan itinerary, feel free to skip things or add some other things based on your own interests and energy level.

So without further ado, let’s dive right into what to see in Old San Juan in one day!

9am: Arrive and grab a quick coffee/ pastry

Whether you are staying in Old San Juan or the nearby touristy areas of Condado or Isla Verde, aim to get to Old San Juan by 9 o’clock in the morning.

The reason I recommend getting here by 9 is that road is relatively empty at this time and you can easily find a spot in the parking garages. There are several garages but the “good” ones do tend to fill up.

After arriving, grab some delicious pastries and coffee from Spiga (or another coffee shop) before you start exploring the colorful Old San Juan.

9:30 to 10:30am: Explore the colorful streets of Old San Juan

There is no shortage of colorful houses and nice photo spots in the Old San Juan, and pretty much everywhere you go, you will see the rainbow colored houses and blue cobble stoned streets.

Depending on where you park your car, you can either explore the west side of Old San Juan or start from the middle. For the purpose of this itinerary, we will start in the middle. The places to stop by include:

• Plaza de Armas : a historical town square in Old San Juan that was officially designated as the central plaza. In this plaza you will find the mayor’s office, a fountain featuring statues that represent the 4 seasons, a Christmas tree (if you visit in December), a couple of cafes, and restaurants and stores on the side.

• Calle de la Luna , Sol St , Calle de San Justo are some of the cutest streets to walk down to see the colorful houses. You will also find restaurants and cafes on these streets. But if you are looking for Instagram photos, these streets are definitely the most instagrammable ones.
• Latita Cafe Murals : The main attraction of this cafe is not necessarily its coffee, but the winged murals outside of the coffee shop. There are two sets of wings, one for kids (suitable for 3-4 year olds) and one for adults.

• Callejon de la Puerta Bandera : The most noteworthy thing on this street is the door painted with the Puerto Rican flag. Walk a block or more towards Museo de San Juan and you will find even more colorful houses.
• Puerto Rican Flag Door : This is another super popular Instagram photo spot in Old San Juan, featuring a black and white Puerto Rican flag painted on the door of a very old and abandoned building.

10:30-12pm: Visit Castillo San Felipe del Morro

After you see the doors with Puerto Rican flags, go up north to the main road of Bulevar del Valle (Calle Norzagaray), go left and walk towards Castillo San Felipe del Morro, one of the two citadels in Old San Juan.

Located at the western tip of Old San Juan, Castillo San Felipe Del Morro is a Unesco World Heritage Site. It was used as a military fort by the Spaniards after it was built in 1790. The fort featured high walls that surrounded the city as well as different levels of ramps, cannons and barracks that protected the city from attacks from sea.

The reason I recommend visiting this fort earlier in the morning rather than going in the afternoon is that there is not much shade at the fort and San Juan can get REALLY hot and sunny. I don’t think you want to be exploring this in the melting heat at 2pm in the afternoon.

It costs $10 (USD) to visit this fort as well as San Cristobal Fortress within 2 days (so you can technically visit one today and another one the next day). Children under 16 can get in for free.

No cash is accepted at Castillo San Felipe del Morro so you must pay with credit cards.

While you are at Castillo San Felipe del Morro, be sure to explore all levels of the fort, take a look at the beautiful Cementerio Santa Maria Maqdalena de Pazzi (a beautiful cemetery) and enjoy a stroll on the lawn outside of the fort. You can also buy a kite from a local store to fly on the lawn (but I saw most people failed to get their kites up).

You can expect to spend at least 90 minutes at the fort and you could spend more time if you are a history buff (or if you spend more time flying a kite outside on the lawn).

12-12:30pm: Cuartel de Ballajá

After exploring the fort and on your way to lunch, do a quick stop at Cuartel de Ballaja , a beautiful courtyard that houses the Museum of the Americas, the Museum of Our African Roots, and the Museum of Popular Arts.

This courtyard is significant as it used serve as a Spanish military barrack and it was the last building by the Spaniards in Puerto Rico.

If you are into arts, you may spend some time exploring the museums. But if you are like me and don’t really care much about arts, then take a quick stop and grab a photo, or grab coffee from Don Ruiz Coffee, one of the best coffee shops in Old San Juan.

1-2:30pm: Lunch in Old San Juan

Finally it’s lunch time! There are a ton of good restaurants so you have a lot of choices. Some of the most popular lunch spots include Deaverdura and Barrachina.

However keep in mind that the popular restaurants also tend to have a long wait. Another thing I noticed is that sit down restaurants can take quite a while! This is so different from restaurants in New York City that I was surprised how long a meal takes.

Unless you are just grabbing a sandwich or something quick, I would recommend setting aside at least an hour to 90 minutes just for lunch.

2:30-4:30pm: Explore more of Old San Juan

There is still a lot left to explore in the Old San Juan and you have a lot of options now.

• Casa Blanca : this museum used to be the home of the Ponce de Leon family. It was the first fortified building in Old San Juan and now it is a museum open to the public.
• Puerta de San Juan : This iconic gate is one of the remaining entrances to the walled city. Constructed in the 16th century, the gate was originally part of the extensive defensive walls built to protect the city from potential invasions. It served as a crucial entry point for ships and traders during the colonial era. You would not miss this red door when walking along the water on the western end of Old San Juan.

• La Fortaleza & the “Umbrella Street” : the governor’s residence used to be a castle built to defend the city. It has now served as the governor’s residence since the 16th century. What’s noteworthy is the street leading up to La Fortaleza (Calle de la Fortaleza) is also known as the “umbrella street” with colorful umbrellas hanging above it. But sometimes the decorations change and it’s not always umbrellas.

• Fuente Raices & Paseo de La Princesa : As you finish exploring the west side of Old San Juan, ultimately you will come to the famous fountain Fuente Raices and Paseo de La Princesa, one of the most scenic and famous streets in Old San Juan.
• Shopping at outlet stores : Did you know that there are some outlet stores in Old San Juan, such as Coach, Guess, and Polo Ralph Lauren? Besides the outlet stores, there are also other chain and local stores as well as souvenir shops and jewelers. I am leaving shopping in the afternoon in case it gets too hot outside so you will appreciate the AC inside.
• Plaza Colon & I <3 SJ Sign : This is another public plaza on the east side of Old San Juan. The statue at the plaza was erected on the 400th anniversary of the discovery of Puerto Rico. At the plaza you will also find the I <3 SJ sign, a popular photo spot!

• Castillo San Cristobal : This is the fort at the eastern end of Old San Juan. Built between 1634 and 1765, this fort was also built by the Spaniards to defend the city. It is larger than the other fort and the ticket you paid would also cover this fort. However I think you just need to visit one, but you can always take photos outside of the fort.

• I <3 PR Sign : Now that you are on the east side, walk down to the cruise ship pier and find the I <3 PR Sign, another cute photo spot that you cannot miss.

4:30-7pm: Bar & Dinner in Old San Juan

After an eventful day of exploring the colorful Old San Juan, it is time to relax and enjoy some drinks and food.

There are a number of highly rated bars and restaurants in Old San Juan.

You can always grab a drink and chill at La Casita de Rones and try their Pina Colada or chill at Scryer Rum Barrelhouse & Rooftop or Antiguo 26. Or you can always hop to different bars or join a bar crawl and try a few different places and drinks.

Where to Eat in Old San Juan

Since we are on the topic of food, you are in luck because I have a ton of restaurant recommendations in San Juan for you. But keep in mind that most of these places are pretty touristy (I mean you are in a very touristy spot).

Breakfast and brunch in Old San Juan

• Chocobar Cortes : known for everything chocolate. You can even get a chocolate martini and chocoburger. Their chocolate milk actually had real chocolate pieces in it!
• Cafe Cuatro Sombras : popular cafe known for their avocado toast and guava n cheese toast. If you want perfect Puerto Rican coffee, this is also a place to go.
• Cafe Mimosa : Feeling mimosa for your brunch in San Juan? Located inside the Casablanca hotel, this little spot is perfect for a quick brunch. Get the waffles and french toast while you are there.

Coffee shops in Old San Juan

You can never go wrong with Puerto Rican coffee and you are in luck because there are some pretty good coffee shops in Old San Juan.

• Spiga : This small quaint coffee shop is a great stop if you happened to park your car in the Dona Fela parking structure. They have both savory and sweet pastries and I really loved both the Guava butter pastry and their savory pastry. Their coffee was great and basic, you won’t find things like Mocha here though.
• Ron Ruiz Coffee : This little coffee shop is inside Cuartel de Ballaja and you will find it only if you are looking. They have one of the best coffees in Old San Juan and they also have sandwiches and other food. There are seatings inside and outside.

Ice cream & Desserts in Old San Juan

• Drunken Cookies : The name says it all! This bakery is famous for their rich soft cookies as well as cookie shots (with alcohol). You will find all different flavors for the cookies as well as cookie made shot glasses with or without alcohol (or you can have craft milk).
• Anita La Mamma del Gelato : This spot is super popular with long lines. You will find a ton of different flavors as well as coffee.
• Zippops Gourmet Paletas : If creamy gelato is not your thing, then go a block east to Zippops Gourmet Paletas, where you will find fresh fruit pops.

Popular restaurants in Old San Juan

There is no shortage of restaurants in Old San Juan, like seriously there are so many so you will need to make a hard decision deciding where to eat for a day.

• Deaverdura :You will find traditional Puerto Rican food and large meat dishes at this colorful restaurant. They have a lot of gluten free options and their sampler platter is the most popular thing to get.
• Restaurante Raíces : One of the most popular restaurants in Old San Juan, Raices has cute decorations inside and offers traditional Puerto Rican food, such as Mofongo, skirt steaks, etc. We ordered fish tacos and the famous Kan Kan pork chop, both were delicious and portions were large.
• Barrachina : As the place where Pina Colada was born, Barrachina gets a lot of love from tourists. You can expect a bit of a wait due to its popularity.
• Marmalade : This upscale restaurant is one of the restaurants that multiple people recommended to me. Believe it or not, this restaurant is known for its white bean soup and people that recommended this place didn’t even like white beans, but they certainly loved the soup.

Where to Stay in Old San Juan

If you happen to spend a night or two in Old San Juan, you will find a number of chain hotels as well as boutique hotels in Old San Juan.

The best boutique hotel in Old San Juan is Hotel El colonial , an adult only hotel near Castillo San Cristobal on the eastern side. The room is tastefully decorated with amazing service. There is a free open bar which is a bonus.

Another boutique hotel in Old San Juan to consider is Hotel El Convento , which is super cute and many instagrammers love to come here for photos. The hotel has a rooftop pool with an amazing view of the water. It is also pretty much located in the center of Old San Juan, making exploring much easier.

Other questions you may have about Old San Juan

How to get around Old San Juan

The Old San Juan is very walkable and it is absolutely the best way to get around. The streets are narrow and there is a lot of traffic, especially on the south side of Old San Juan.

Get time to visit Old San Juan

Mid November to late March is the best time to visit San Juan in Puerto Rico.

Being a Caribbean island, Puerto Rico has a tropical season. The temperature stays relatively constant, between 70F (lowest) and 90F (highest) throughout the year.

You can expect more humidity and fewer clear skies between April and November with the most uncomfortable months of July and August.

Can I use credit cards in Old San Juan

Credit Cards are actually the best payment methods in Old San Juan. Almost all restaurants, shops, bars and cafes accept credit cards.

If you plan to visit the forts, you can only pay by credit cards, cash is not accepted. However keep in mind that some souvenir stores may have a minimum of $5 to $10 before you can pay with credit cards.

Can I use US SIM cards in Old San Juan

Yes! US SIM cards and phones work perfectly fine in Puerto Rico. There’s no international roaming charges.

Do I need a passport to visit Puerto Rico

You do not need a US passport to visit Puerto Rico, the flight is treated as a domestic flight if you are flying from the US.

Is Old San Juan kids/ stroller friendly

You can push a stroller on the sidewalks of Old San Juan. Occasionally you may need to carry the stroller up/down a step if there is no ramp but 90% of Old San Juan is stroller friendly.

However, do keep in mind that Old San Juan can get really busy with a lot of people on the sidewalks, so it may be annoying to navigate with a stroller.

If you were to bring a stroller to Old San Juan, you should bring a lightweight one. I do not recommend bringing a large and chunky stroller like Uppababy Vista.

Is Old San Juan safe? For female solo travelers even?

Old San Juan is very safe, even for old female travelers. With that said, you should always watch your surroundings and your things. Keep your bags zipped and close by.

There is a neighborhood called La Perla on the very northern side of Old San Juan by the water. It was once known as one of the most dangerous neighborhoods in San Juan.

La Perla was featured in the music video Despacito and actually sort of became a tourist attraction. You probably wouldn’t wander there anyway but I would not recommend going. If you do end up going there, be respectful, don’t take photos and videos of people’s businesses and houses.

Where to park in Old San Juan?

There are several parking lots and parking garages in Old San Juan, with Multipiso Doña Fela and La Puntilla Parking lot being two of the most popular ones. I personally parked in Multipiso Doña Fela and was very happy with my choices.

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OLD SAN JUAN HISTORY WALKING TOUR

Quick Details

• Hour Glass Duration: 2 hours
• Users Capacity: Requires a minimum of 5 participants, maximum 15
• Walking Effort Level : This walking tour involves moderate physical activity, requiring a reasonable level of fitness or mobility. Participants must be able to complete this tour without walking aids.
• Wheelchair Accessibility: If you have mobility concerns, feel free to contact us before booking to discuss alternative recommendations for your needs.
• Clock Check-in: Arrive 15 minutes early for check-in before your tour.

Unveil Centuries of History in a Small Group Setting

Our walking tour immerses you in the rich history of Old San Juan. As we stroll through historic landmarks, we share the narratives woven into the streets, exploring themes of indigenous and ancestral cultural heritage, colonization, and mesmerizing architecture.

Join us on this shared adventure, peeling back the layers of Old San Juan’s rich tapestry.

• Chevron down What's Included?
• Guided walking tour of Old San Juan
• Professional Tour Guide certified by the Puerto Rico Tourism Company
• Chevron down What's not Included?
• Entry to Castillo San Cristobal or Castillo San Felipe del Morro is not part of the tour.
• Access to the inside of any buildings during the tour is excluded.
• Tipping is optional but appreciated.
• Chevron down FAQs

To ensure a smooth experience, let’s address some key details:

• Tour Specifics This is a walking tour in its entirety.

If the minimum is not met, we will offer:

• rebooking the same tour at a different time
• rebooking into a Private Tour with 15% discount, based on availability
• full-refund cancellation with 48 hours notice, giving you plenty of time to find an alternative tour.
• Transportation Unfortunately, we do not provide transportation. Please arrange your own to our meeting point.
• Wondering where to park your rental in Old San Juan? You can find parking options at: Doña Fela Parking, La Puntilla Parking, and Multipiso Covadonga.
• Restrooms Restrooms are available along the walking route for your convenience.
• Is there an additional charge associated with this tour? Online purchases include a 6% convenience fee.
• Planning to join us on short notice? Same-day bookings are unavailable, so we recommend securing your reservation in advance for a stress-free experience.
• Languages Spoken Our guides speak English and Spanish. Upon request, we can accommodate tours in both languages to enhance your experience.

Should you have any further inquiries, do not hesitate to reach out to us at [email protected] .

Should you have any further inquiries,  do not  hesitate to reach out to us at [email protected]

• Chevron down Health & Safety Policy

Your well-being is our top priority!

At My Puerto Rico Tours, your safety is our paramount concern. Our Health & Safety Policy is designed to ensure a secure and enjoyable experience.

Please take note of the following detailed guidelines:

• Hydration Essentials Remember to carry water to stay adequately hydrated during your activities.
• Footwear Recommendations Opt for comfortable walking shoes to ensure ease and safety.
• Weather-Appropriate Dress Code Choose light, breathable clothing suitable for tropical weather for your comfort.
• Sun Protection Measures Shield yourself from the sun using a hat, sunglasses, and sunscreen to prioritize your well-being.
• Weather Resilience Commitment Rain or shine, our tours go on. Stay informed on weather conditions to enhance your preparedness.
• Chevron down Cancellation Policy

Customers will receive a full refund with 48 hours notice of cancellation. Cancellations made less than 48 hours in advance will be eligible for a 50% refund. In case of operator cancellation due to weather or other unforeseen circumstances, customers will also receive a full refund.

No-shows or cancellations on the day of the tour will not be eligible for a refund.

To cancel or inquire about rebooking your tour, please contact us:

• Phone: +1 (939) 475-4386
• Email: [email protected]

We appreciate your understanding and cooperation.

• Chevron down Customer Reviews

Note: We’re Back! 🎉

After a brief hiatus, we’re thrilled to announce our comeback!

We appreciate your patience and continued support. Here’s a glimpse of what our customers have said about their experiences.

Informative, entertaining tour – highly recommended!

First time to Puerto Rico and My Puerto Rico Tours made this an awesome visit.

Thank you for being part of our journey! – Carlos & Alexandra

35 Best Things to Do in Old San Juan Walking Tour & Map

• Post author: Lisa Garrett
• Post last modified: March 30, 2024
• Post category: Caribbean / Cruise Ports / Favorites / USA

Disclaimer :  This page may contain affiliate links.  I earn a small commission if you make a purchase through these links (at no additional cost to you).

Planning a visit to San Juan, Puerto Rico? There are so many amazing things to do in Old San Juan!

This is one of my favorite Caribbean cruise ports, and you’re going to love it!

I’ve visited as the embarkation point for a cruise and also for a day as a cruise port stop. I’m always amazed by all the great things to do in Old San Juan Puerto Rico .

Historic San Juan is a compact area and very easy to explore on foot. So, you can see plenty of great attractions during your cruise port day in Old San Juan.

Are you ready to book your trip to San Juan?

Looking for the top picks for your trip to San Juan ? Here are some of the best tours and hotels to help you plan the perfect vacation!

Top Tours and Experiences in San Juan:

• Flavors of San Juan food tour (Award-winning tour with 3300+ 5- star reviews!)
• Mixology class at Casa BACARDÍ (Distillery tour + cocktail-making class!)
• Old San Juan Segway Tour (See 25 top attractions on this small-group tour)
• Craft Cocktail walking tour (Old San Juan cocktail + history tour)
• Old San Juan walking tour (Top-rated tour with local author guide)
• Sunset Harbor Cruise (A romantic way to end your day in Puerto Rico!)

Top Hotels in Old San Juan:

• CasaBlanca Hotel (We stayed here before our cruise. Enjoy the rooftop deck with stone bathtubs overlooking the city!)
• Hotel El Convento (Fabulous 4-star hotel in a former convent!)
• Sheraton Old San Juan (Best-selling waterfront hotel with a rooftop pool!)

If you’re lucky, your cruise ship will dock in Old San Juan. (We were happy that our Caribbean cruise did!)  This makes it very easy to hop off the ship and take a Viejo San Juan walking tour of all the amazing sights.

Wondering what to do in Old San Juan Puerto Rico ? I’ve got information on all the top San Juan sights right here for you (along with a handy map to point you in the right direction).

Lace up your shoes and let’s go!

Table of Contents

Best Things to Do in Old San Juan Puerto Rico

1. take a guided walking tour of old san juan.

Old San Juan is the perfect place to take a walking tour . Since it’s such a small area, you can certainly cover a lot of the historic city and see many incredible landmarks .

However, just winging it sometimes results in missing out of some really awesome sights. Trust me — that’s what happened to us on our first visit to San Juan. I hate it when I’m just back from visiting a city and a friend says ‘did you see X? It’s the best!’ Doh!

Taking a guided walking tour is a great way to get a feel for the layout of this historic city. Plus, you’ll learn a lot more about the unique culture and history of Puerto Rico while you see some of the city’s best sights. You’ll even get tips to help you maximize the rest of your sightseeing.

You’ll find many great walking tours to choose from. The best Old San Juan walking tour has over 900 5-star reviews. Your guide is a local author, so you know you’ll hear plenty of amazing stories as you take in the sights!

On this small group walking tour of Old San Juan, you’ll see top landmarks such as the Paseo de la Princesa, Calle de la Fortaleza, Castillo de San Cristóbal, and more.

See the top highlights of Old San Juan while being entertained with stories about the history of this unique city on this Old San Juan Walking Tour .

Prefer to explore on your own? That’s what we typically do!

If you’re short on time, the 11 starred items on the list below will give you a great taste of the top attractions in Viejo San Juan Puerto Rico . (And they make a convenient loop from the Old San Juan cruise port.)

2. See the Puerto Rican city crests at Plaza Dársena ***

If you’re arriving by cruise ship and have docked in Old San Juan, hang a left as you exit the dock and head west.  The first thing you’ll run across is the lovely Plaza Dársena , also known as Plaza de la Marina. 

This plaza overlooks San Juan Bay and has little tables and benches where you can relax and watch the ships in the harbor.

On the eastern side of the plaza is this gorgeous fountain .  The sparkling blue waters of the fountain really pop against the backdrop of this vibrant pink building (the La Casita de Rones restaurant).

Be sure to take a look at the ground around the base of the fountain.  You’ll find several mosaic coats of arms here.  These represent different cities and villages in Puerto Rico.  You’ll also find these mosaic city crests on the northern side of the city, in Plaza San Juan Bautista.

3. Admire Art Deco architecture from Plaza de Hostos

One thing you’ll be quick to notice is how many plazas there are in Old San Juan, just as you would find in iconic Spanish cities such as Madrid and Barcelona . 

Some of them are quite grand, while others are more modest.  You may find statuary, fountains, gardens, or shady benches to enjoy in a plaza.

The Plaza de Hostos is one of the more modest plazas in San Juan.  It honors famous Puerto Rican independence advocate Eugenio María de Hostos. 

Take a moment and look to the north of the plaza.  Rising eight stories is the stunning sleek building housing the Banco Popular de Puerto Rico.  This is a gorgeous building in the Art Deco style. 

If you look closely, you can see reliefs flanking the intricate central window.  Some of these represent Roman gods (Mercury, Ceres) while others represent attributes that make for good banking (wisdom and security).

Tip: Plaza de Hostos and the Banco Popular are popular tour meeting points . So this is a good place to be able to find!

4. Enjoy local cuisine on a food tour

The best way to get to know a culture is by sampling its cuisine. You’d be missing out if you didn’t try some of local Puerto Rican favorite dishes!

• Mofongo : Mofongo is a must-try when visiting San Juan. This flavorful dish consists of mashed plantains mixed with garlic, olive oil, and chicharrones (crispy pork skin) or other fillings.
• Tostones : Tostones are a popular dish in Puerto Rican and Caribbean cuisine. They’re made from green plantains that are sliced, fried, smashed, and then fried again until they’re crispy and golden brown.
• Trembleque : This creamy coconut pudding, whose name translates to “trembling,” gets its moniker from its jiggly, wobbly texture. My good friend Keren (from Puerto Rico) made my family trembleque for the holidays and it was delicious!
• Rum : (This one needs no explanation!) Puerto Rico is known as the rum capital of the world! Visit Casa BACARDÍ and enjoy a rum tasting and distillery tour or this fun mixology class !
• Piña colada : Speaking of classic Puerto Rican drinks, we can’t forget about the piña colada. It’s one of my favorite cocktails, and it was invented right here in Puerto Rico! Enjoy some specialty cocktails on this Puerto Rico Craft Cocktail Walk .
• Coquito : Coquito is creamy, coconut-infused drink with a hint of rum. It’s kind of like eggnog but with a distinct island twist. It’s the perfect blend of sweet, rich, and indulgent, making it a beloved holiday treat in Puerto Rico. (Keren made this for us too. Yum!)

Check out these great food tours in San Juan — your taste buds will thank you!

5.  Look at the adoquines (blue cobbles of Old San Juan) ***

Be sure to take a look down as you are exploring Old San Juan.  You’ll see the roads use distinctive blue cobblestones , called adoquines .  There are a few different explanations for how these blue cobbles came to Viejo San Juan, but both of them have a flavor of colonialism.

Sources indicate that the original materials traveled to Puerto Rico as the ballast on Spanish ships .  These stones were dropped off to free up cargo space to carry precious natural resources from Puerto Rico back to Spain . 

The stones were then used to build various things in Puerto Rico including pavers for the roads.  Over time, the slag turned blue from exposure to the elements.

The US did a lot of renovation in Puerto Rico to bolster the idea of its Old World charm and hence to enhance its desirability as a tourist destination .  This even included ordering new cobblestones to line the streets (newly manufactured to look like aged, weather-worn cobbles).

These blue cobbles are part of Old San Juan’s identity, and you can even see them as creative foundation for San Juan’s artisan community.   

I found this lovely piece of art on display, available for you to take home as a souvenir of your visit to Puerto Rico.  Noel Estrada’s ‘ En Mi Viejo San Juan ’ is a famous song of nostalgia for Puerto Rico.

6. See the ornate San Juan Customs House

The San Juan Customs House is a very ornate Spanish Colonial Revival building.  It was built in 1924 and is listed on the National Register of Historic Places.  You can’t miss this sprawling two-story pink and white concrete building with its arched windows and doorways. 

The Customs House features terra cotta embellishments in the plateresque style, which is a Spanish architectural style featuring intricate, silversmith-like detailing.   The terra cotta is further accented with bright colors and includes patriotic motifs such as the eagle. 

The Customs House was under construction on our visit – it is undergoing a massive multi-million-dollar renovation –so we could only get a picture of the rear of the building.  The front side, facing the harbor, is much more spectacularly decorated.

7. See the Old Arsenal of the Spanish Navy

La Antiguo Arsenal de la Armada Española translates as ‘the Old Arsenal of the Spanish Navy’.  The thought of the Spanish Armada certainly conjures a trove of mental images featuring treasure-laden galleons, cannons, and pirates.

The Arsenal is a Neoclassic building constructed in the 1800s by the Spanish.  As you can guess, it stored weapons and ammunition.  It became used as government offices after the Spanish-American War.  Today, you’ll find it used to showcase cultural events and art exhibitions if you time your visit right.

The simplicity of the Arsenal’s design is a significant difference to its fancy neighbor, the US Customs House.

8. Stroll along the Paseo de la Princesa ***

The Paseo de la Princesa is a wide paved sidewalk framed by trees and ornately wrought lamp posts.  It heads due west towards the sea and the fabulous plaza containing Fuente Raíces.  There are many benches bordering the wide walkway where you can relax in the shade and engage in some people-watching.

Since it is such a photogenic location , you’ll find a lot of folks here trying to get that Insta-worthy shot.  You’ll likely need to wait your turn for a perfect Paseo de la Princesa picture.  We had to wait a bit while two ladies worked really hard to get the best photo for their social media.

I’m not kidding – the gal in yellow was the subject of the impromptu shoot.  Her friend, clad in black, gave her instructions like ‘suck in your gut’ and ‘hold your foot up like you’re walking’.  We kind of giggled at this since very few of our vacation photos contain pictures of us.

Note there are some public restrooms in a small building on the south side of the Paseo de la Princesa, close to its eastern end.  There were other public restrooms indicated in Google maps in Old San Juan, but these were the only ones we were actually able to locate.

9.  Relax in the Jardin del Paseo la Princesa

Most people dash west along Paseo de la Princesa to the fabulous fountain at its western end.  But if you do that, you actually miss out on some pretty cool stuff.   So, it pays to take your time and explore all the little nooks and crannies that you run across in Old San Juan.

To the north, you’ll find the Jardin del Paseo la Princesa .  This lovely little garden plaza sits between the Paseo and the high fortified walls surrounding old San Juan.  This is one of my favorite hidden gems in Old San Juan .

The garden features lush plantings and a gorgeous fountain .  It also contains this wonderful statue of a woman all dressed up in a floral suit accented with pearls and her fan.  

And, just in case you were looking to get in a little aerobic exercise during your trip to Old San Juan, you’ll find a parkour course squished in between this garden and the looming city walls. 

10. Fuente de la Herencia de las Américas 

Continuing west from the Jardin del Paseo la Princesa, you will find Fuente de la Herencia de las Américas.  This translates as Fountain of the Heritage of the Americas – which is a bit misleading as I couldn’t find a fountain.

Instead, you will find a small plaza with a symmetrical double staircase.  There are three bronze statues at the top of the staircase, with two additional statues flanking the plaza. Sculptor José Buscaglia created these statues, which together serve as a reminder of colonialization and Hispanic heritage .

11. Pop into the former prison of La Princesa

As you stroll toward the sea along Paseo de la Princesa, you’ll note a grand historic building to your right:  La Princesa .  At one time, La Princesa was a prison . 

Today, it houses a tourist information office and an interesting art collection.  You can stop in and get a nice map of Puerto Rico including a detailed map of Old San Juan.

The lady staffing the information desk let us know that we could view some of La Princesa’s original prison cells .   So, of course, we had to take a quick peek. 

Walk straight through the building and out the back door.  You will find a narrow passageway on the right leading to the cells, with the fortified city walls looming large in the background.  Not my preferred San Juan accommodations, to be sure.

12. See the lovely Raices Fountain ***

Raices Fountain (Fuente Raíces) is located in a grand plaza at the westernmost end of Paseo de la Princesa.  The shimmering waters of the bay serve as a lovely backdrop to the plaza’s majestic fountain — a must see in Old San Juan!

Unveiled in May of 1992, Fuente Raíces celebrates the 500 th anniversary of Spain’s ‘discovery’ of the New World.  The fountain’s bronze statues represent gods and goddesses of the Taino, African, and European cultures which make up Puerto Rico’s cultural heritage, or roots.

This is one of the most gorgeous locations in Old San Juan . So, it is understandably very popular for photos. 

Just as a tour group cleared out and we were ready to take our pictures, we were dismayed that the waters of the fountain turned off.  Luckily, after a few moments they resumed and we were able to get some fantastic photos of this Puerto Rican landmark .

From Fuente Raíces, if you look to your north, you can get a good view of La Fortaleza, the governor’s mansion.

13. Walk along the El Paseo del Morro National Recreational Trail ***

Head north from Fuente Raíces and you’ll find El Paseo del Morro National Recreational Trail .  This waterside trail is one of the best activities in San Juan Puerto Rico (and one of my personal favorites!).

This paved one-mile trail is an easy walk that will take you to Paseo del Morro, the headlands underneath Castillo San Felipe del Morro, one of Old San Juan’s forts. 

There are interpretive displays along the way which provide you with historical insights.

This is a picturesque stroll : to your right are the imposing fortified city walls of Old San Juan, studded with garitas (sentry boxes).  And to your left, you have an expansive view of the sea with ocean waves rolling in and crashing on the rocks. 

It is easy to get caught up in the excitement of what amazing things you’ll find around the next bend.  But don’t forget to take a look back at where you’ve been.  As you reach the end of El Paseo del Morro National Recreational Trail, you can get a fantastic view looking back towards Fuente Raíces. 

The castle-like governor’s mansion, La Fortaleza, gleams in the sunshine atop the city walls.

14. Walk through the San Juan Gate ***

The Puerta de San Juan , or San Juan Gate, was the main access point to Old San Juan for visiting dignitaries and travelers during Puerto Rico’s Spanish colonial era .  The gate’s towering wooden doors would have been closed and barred at sundown to protect the city from invaders.

There were originally several such gates in Old San Juan, but this one is the last one remaining today. 

The massive San Juan Gate is painted a vibrant red, which really makes it stand out against the surrounding stone.  

The doorway passes through the city walls and measures sixteen feet high and twenty feet thick.  The Puerta de San Juan as you see it today was built in 1635 (with various restorations since).

The San Juan Gate was named after Saint John the Baptist.  At the top of the gate the inscribed Latin text reads “Benedictus qui venit in nomini Domini”.  This translates to “Blessed are they who come in the name of the Lord”, and reflects Puerto Rico’s Catholic roots.

If you want to pop through the San Juan Gate into Old San Juan for refreshment before continuing along the trail towards the fort, this is your opportunity.

15. Watch the cats at Parque de Los Gatos

As you walk along El Paseo del Morro National Recreational Trail, take a close look at the shrubbery lining the pathway.  Chances are, you’ll see quite a few cats dozing in the shade or stalking a bird or a lizard.

There is a large feral cat colony along El Morro Trail.  Save-a-Gato is a nonprofit organization dedicated to improving the welfare of the cats of Old San Juan.  It has an agreement with the National Park Service to care for the cat colony along Paseo del Morro.

Save-a-Gato traps, neuters, and vaccinates the cats you find along this stretch of national parkland.  They work to find homes for the stray cats of Old San Juan, but cats that are feral and non-adoptable are returned to this colony.  The volunteers provide food and water for this feral cat colony to ensure their well-being.

Although most of the cats keep to themselves, this dapper fellow hopped up on a boulder and obligingly posed for our photo.

16. Enjoy the views from the Paseo del Morro viewpoint

El Paseo del Morro National Recreational Trail ends at the tip of the peninsula, guarded by Castillo San Felipe del Morro looming overhead.   From here you have a decision to make. 

One option is to walk back along the trail towards the Puerta de San Juan and Fuente Raíces.  If you’re ready for a bit more exertion, you can choose to climb the stairs to Castillo San Felipe del Morro and explore the fort .

But, before you do either of those things, take a few minutes to enjoy the views .  Watch the waves rolling in and crashing along the rocks.  I always find the sound of water relaxing (and have ocean waves as my white noise to fall asleep).  Here’s a little video of the surf from this viewpoint:

17. Explore the historic fortress of El Morro ***

Castillo San Felipe del Morro , commonly referred to as ‘ El Morro ’, is one of Puerto Rico’s historical defensive structures and impressively spans six levels. 

This citadel was constructed during the 16 th through 18 th centuries.   It is part of the San Juan National Historic Site , a UNESCO World Heritage Site , and is one of the top San Juan attractions. 

Across the bay from El Morro is a smaller fort, Fortín San Juan de la Cruz (called El Cañuelo ).  These two forts protected the bay by setting up a deadly crossfire that would block enemy ships from being able to enter the harbor.

If you are arriving in San Juan by cruise ship, you can’t miss it as you near the island and enter the harbor.  It’s one of the best sights in Old San Juan!

Here you view the grand fortress of El Morro protecting the harbor.  In the background you can glimpse the colorful buildings of La Perla , Old San Juan’s historical shanty town.  La Perla is actually built outside of the city walls.

Visiting El Morro

After you climb up the stairs from the Paseo del Morro Trail, you’ll reach the grounds of the fort – which are actually quite extensive. 

You can explore the grounds for free , but if you want to tour the fort and visit its museum, you’ll need to pay a fee.  (Note that this ticket will also grant you entry to Old San Juan’s other major fort, Castillo San Cristóbal.)

Castillo San Felipe del Morro has played an exciting role over the centuries in protecting this Spanish port.  El Morro’s defenses and artillery were key in defending Puerto Rico against attacks from the British, the Dutch, and the pirates of the Caribbean.

By the time of the Spanish-American War, El Morro’s impressive defenses had become outdated, and it was not able to withstand advanced weaponry.  During the two World Wars, El Morro was used as an active US military base .  Today, it is a museum operated under the National Park Service .

If you visit Castillo San Felipe del Morro from the land side, you’ll approach across this grand expanse of lawn called a glacis .  While scenic, it is actually yet another of the citadel’s defensive features.  A glacis is a plain gently sloping downward from a fort which exposes attackers to the weaponry of the defenders.

Interested to know more about El Morro? Watch this brief video from the Smithsonian Channel:

18. View the Cementerio Santa María Magdalena de Pazzi

On the northern edge of El Morro’s glacis and just outside of its walls, you’ll find the Cementerio Santa María Magdalena de Pazzi.  This ornate cemetery overlooks the ocean and is the final resting place of many famous Puerto Ricans.

The most prominent and eye-catching feature of this cemetery is its chapel.  Capilla del Cementerio Santa María is a circular building with arches and columns all around, topped by a red dome.  You will also find many gorgeous statues gracing the tombs.

19. Visit Casa Blanca, built for Ponce de Leon

Casa Blanca (not to be confused with the San Juan hotel of the same name) is a house that was built for Ponce de Leon.

You may remember him from your history books as a famous Spanish conquistador. But you probably don’t know that he was also the first governor of Puerto Rico.

Unfortunately, Ponce de Leon passed away before Casa Blanca was complete. Dating from the year 1521, Casa Blanca is the oldest residence in Old San Juan. And today it serves as a house museum filled with artifacts from the 16th and 17th centuries.

20. Visit a museum at the Cuartel de Ballajá

The Cuartel de Ballajá, or the Ballaja Infantry Barracks Building , was constructed from 1854-1864 to be used as housing for the Spanish soldiers and their families.  This majestic 3-story building covers six city blocks and features a grand interior courtyard.   During WWII it served as a military hospital and then later fell into disuse. 

The Cuartel de Ballajá was restored as part of the 500 th anniversary, with the intent of supporting cultural and educational purposes.   

It now houses the Museo de las Américas , a museum featuring Latin American Art.   The museum showcases three permanent collections:  Popular Arts in the Americas, The African Heritage, and Conquest and Colonization: Birth and Evolution of the Puerto Rican Nation.  

21. See the giant totem pole in the Quincentennial Plaza ***

The Plaza del Quinto Centenario (Quincentennial Plaza) is the highest point in Old San Juan.  Built in 1992, the Plaza commemorates the 500 th anniversary of Christopher Columbus’ first voyage to the New World. 

The focal point of the plaza is a 40-foot-tall totem pole , El Tótem Telúrico.  This totem is constructed of clay from across the Americas and symbolizes the origin of the New World.

From the totem you can look across the expanse of the grand Plaza and enjoy the ocean views .  There are benches scattered around the plaza if you want to give your feet a break!

22. Photograph the colorful buildings of Old San Juan ***

Take a peek down any street in Old San Juan, and you’ll see a lovely jumble of colors and styles.  Colorful buildings are common in the Caribbean , as bright colors help to reflect the rays of the sun and keep the interior rooms cooler.

The buildings contain hotels, restaurants, and shops all vying for your attention.  The bright, rainbow-colored buildings are accented with white-framed doorways and windows and decorative wrought iron balconies . 

This is definitely one of the best things to see in Old San Juan !

This view is down Calle de San Francisco.  At the street’s end, you can catch a glimpse of Castillo San Cristóbal, the largest Spanish fort in the New World.

23. See the Catedral Basilica Menor de San Juan Bautista ***

Catedral Basilica Menor de San Juan Bautista was first built on this site in 1521.  After being destroyed by a hurricane, it was rebuilt in 1540. Thus, it is the second-oldest cathedral in the Americas, and the oldest church on US soil.

You’ll note the Cathedral is located rather close to the San Juan Gate, the primary point of entry for travelers to the city.  It is said that sailors and visitors to Puerto Rico made this church one of their first stops upon their arrival, to thank God for a safe journey.

The cathedral’s neoclassical exterior is rather plain and austere, painted mostly white with few embellishments.  But the interior is definitely worth a closer look. 

Inside, you’ll find soaring arches, brilliant stained-glass windows , and the tomb of San Juan’s founder, the famous explorer Juan Ponce de Leon .  (The Puerto Rican city of Ponce is named in his honor.)

24. Relax in Plaza de Armas ***

Plaza de Armas is the Old San Juan’s historic town square .  To its north, you’ll find city hall, and to its west, the Puerto Rico Department of State.  The plaza features this lovely fountain anchored by four 19 th century statues .  These four statues, representing each of the four seasons, were originally located on the corners of the plaza.

There are many benches lining the edge of the plaza.  Buy a cup of coffee and a pastry from one of the nearby vendors and entertain yourself with a little people-watching.  Be careful—you might have to fight some pigeons for your snack!

25. Enjoy harbor views from the Bastión de las Palmas de San José

Old San Juan is protected by the fortified city walls, complete with garitas ( sentry towers ) – all part of the San Juan National Historic Site.  As you criss-cross Old San Juan by foot, whenever you reach an ‘edge’ of the old city, you’ll get a great view. 

The Bastión de las Palmas de San José is one such locations.  It is a small plaza with benches, lots of shady trees, and fantastic harbor views . There is a garita here, although there is a door blocking public entry. 

(Looking for a photo op of you or your traveling companion inside a garita?  Some sentry towers are open to the public, such as those at the El Morro fort.)

This plaza does come with a little something extra:  two whimsical cat chair statues .  And perched jauntily on the shoulder of each cat is a bird wearing a hat.  The birds may be intended to be doves, since this bastion is quite close to the Parque de las Palomas .

26. Seek out the Capilla del Santo Cristo de la Salud

Capilla del Santo Cristo de la Salud (Chapel of the Holy Christ of Health) is a tiny chapel on the edge of Old San Juan near the city walls.  It was built in the 18 th century in the Spanish Baroque style, and sports a tiny belfry .  When we were exploring Old San Juan, we overheard a tour guide tell the origin story of this chapel. 

Story has it that a horse race occurred on Calle del Cristo. There was an accident in which one of the riders could not stop his horse, and went over the cliff. 

Stories vary as to who invoked the aid of Santo Cristo de la Salud –the young man or the Secretary of Government — but the young man miraculously survived the fall from the cliff. The Secretary immediately ordered the construction of this chapel to honor the miracle.

Pilgrims visit the Capilla del Santo Cristo de la Salud in hopes of benefiting from its healing powers .  It is only open on certain days and times, so check before your visit if you want to view the interior of the chapel.

Next to the Capilla del Santo Cristo de la Salud you’ll find the Parque de las Palomas.  This translates to ‘Park of the Doves’ or ‘ Park of the Pigeons ’, and you’ll always find flocks of pigeons atop the chapel. 

27. Visit La Fortaleza

La Fortaleza , also known as Palacio de Santa Catalina , was the first of San Juan’s original fortifications and is part of Puerto Rico’s UNESCO World Heritage site .  This fortress was built in the 16 th century to protect Puerto Rico’s valuable harbor. 

La Fortaleza is Puerto Rico’s governor’s mansion .  This impressive structure is the oldest executive mansion to be continuously used in the New World and has housed 170 governors over the centuries.

Stories say that in 1898 as Puerto Rico was invaded by the United States , the last Spanish governor of Puerto Rico hit the longcase clock with a sword.  The clock stopped at that moment and forever marks the time at which Spain lost its control over Puerto Rico.

How to see La Fortaleza

The portion of La Fortaleza facing the harbor looks very much like a medieval castle , complete with a large round tower and crenellations.   The newer additions which face inland feature stately Neoclassic architecture.  You can visit La Fortaleza as part of a guided tour , but you cannot explore on your own.

You get an excellent view of La Forteleza from the harbor.  As you can see in this picture, it gleams a brilliant white in the rays of the setting sun. This makes it a vivid contrast to the stone city walls. 

Be sure to keep an eye out for La Fortaleza as you are sailing out of San Juan as you’re savoring a refreshing a delicious drink on your cruise !

28. Shop along vibrant Calle de la Fortaleza (Umbrella Street) ***

Calle de la Fortaleza is, literally, the road that leads to La Fortaleza. This road boasts many restaurants, shops, and bars and bustles with activity.   Also known as ‘ Umbrella Street ‘, this road is popular for its colorful decorations .

 On the day of our visit, Calle de la Fortaleza was bathed in vibrant pink from the installation of hundreds of pink butterflies strung overhead. 

The overhead art on this road changes over time – sometimes it is decorated with umbrellas in all the colors of the rainbow, sometimes swathed in giant Puerto Rican flags .  Calle de la Fortaleza has become a tourist attraction of its own for these colorful displays.

29. Stroll through historic Plaza Colon

Plaza Colon is a plaza located at what used to be the easternmost edge of Old San Juan.  This plaza (previously known as Plaza Santiago) would have been the first thing seen by visitors entering Old San Juan through its eastern city gate, the Puerta de Santiago . 

The Plaza features, not surprisingly, a monument to Christopher Columbus .  This was erected in 1893 for the 400 th anniversary of the ‘discovery’ of Puerto Rico.  Prior to this, the plaza featured a statue of Juan Ponce de Leon , which was relocated to Plaza San Jose.

The monument features a tall pedestal topped by Christopher Columbus.   The intricately carved statue features realistic textures on Columbus’ clothes and cloak.  At the pedestal’s base, a ship’s prow and looming sea monster protrude from each corner.

Many restaurants and shops surround this popular plaza, often used for markets and vendors.  On its south side, the plaza is bordered by the Teatro Tapia, one of the oldest freestanding theaters in the United States. 

On its east side is the striking Antiguo Casino de Puerto Rico. And, from here you can see the imposing fortress of Castillo San Cristóbal just a stone’s throw to the northeast.

30. Explore Castillo de San Cristóbal

Castillo de San Cristóbal , or Saint Christopher’s Castle , is the third of the triumvirate of fortresses you’ll find in Old San Juan.  It is named after Saint Christopher, the patron saint of land travelers, and is one of the best Old San Juan tourist attractions .

 Construction on Castillo de San Cristóbal began after Puerto Rico’s existing defense system proved unable to sufficiently withstand attacks from the English and Dutch. 

The Spanish really went all-out on this citadel – it is the largest Spanish fort in the New World , covering over 27 acres.  The first shots in the Spanish-American War were fired from this San Juan fort.

Castillo de San Cristóbal is part of the San Juan National Historic site and is open to the public daily.  There is a fee for entry, but your ticket will also allow you to visit San Juan’s other major fort, El Morro. 

Definitely give yourself time to explore the citadel and its interesting defensive features – triangular bastions, sentry boxes, a deep dry moat, and an extensive network of tunnels.   From Castillo de San Cristóbal, enjoy amazing views of the coastline and its sister fortress, El Morro.

You can really get an appreciation of the scope of Castillo de San Cristóbal from a distance – this picture is from the top deck of our cruise ship docked in Old San Juan’s harbor.   In the foreground is the Antiguo Casino de Puerto Rico with its curving metal domed roof.

Garita del Diablo (The Devil’s Sentry Box)

There are plenty of garitas , or sentry boxes, throughout San Juan’s forts and fortified city walls.  One of Castillo de San Cristóbal’s garitas has its own legend:   Garita del Diablo (the Devil’s Sentry Box ). 

This particular garita is the most isolated and projects out further from the coast into the ocean.  Stories say that strange noises were often heard at night here, in addition to the loud crashing of the ocean’s waves.  So, between the unusual noises and its remote location, the guards didn’t like being stationed for duty at this garita. 

At night sentries would shout to check on each other.  One night a soldier named Sanchez was on duty, but didn’t respond to any of his compatriots’ calls.  The soldiers were afraid to check on his safety until dawn – and all they found was his weapon and uniform.  And so, the legend was born that he was taken by the devil.

The more pragmatic offer another explanation:  Sanchez ran off that night with his true love , fleeing under the cover of darkness since her family did not approve of him.  (And yes, in this version, she brought him a change of clothes!)

31. Admire the Old Casino of Puerto Rico

Just south of Castillo de San Cristóbal you’ll find the Antiguo Casino de Puerto Rico .  This beautiful building was constructed in 1917 as a social club, but has changed purpose many times over the decades. 

It served as an officers’ club for the US Army during WWII, the became home to a music school, followed by a cultural institute, and is now an events center and popular wedding venue.

The exterior of the Old Casino of Puerto Rico calls to mind a romantic graceful age.  Tall columns flank the entryway, balconies abound, and its domed metal roof gleams copper in the sun. 

The interior is also gorgeous with white marble floors, a grand staircase, and a sparkling 12-foot-tall chandelier .

32. Tour the Capitol building

Puerto Rico’s Capitol, El Capitolio , is a stately Neoclassical building.  Also known as ‘The Palace of Laws’, it symbolizes Puerto Rican self-government and houses the Puerto Rican legislature.  

The inscription across the Capitol is the Abraham Lincoln quote “Government of the People, by the People, for the People shall not perish from the Earth.”

El Capitolio is open to the public on weekdays, so feel free to take a look around.  Inside the Capitol building you’ll find historic documents on display.  Enjoy the classical architecture and décor, from the marble floors and columns to the detailed paintings on the inside of the dome portraying Puerto Rican historical events.

Cross the road to Plaza San Juan Bautista to enjoy the best views of the capitol .  This grand semicircular plaza honors Saint John the Baptist and features the mosaic city crests like the ones seen at Plaza Dársena.

33. See the magnificent mosaics

Even if you have no need of visiting the Tourist Information office, you’ll want to make a stop at this one.  Be sure to approach from the south side of the building, on Paseo Covadonga.   The tourist information office is a charming salmon-colored building with white accents. 

But the real star of the show is the fantastic art just in front of the office.  There is a gorgeous brightly colored mosaic that stretches over twenty feet in length.  Here are two segments of this mural, and if you look closely, you’ll see the words ‘San Francisco’ and ‘San Cristobal’ in intricate mosaic script.

And, just a smidge further to the west, you’ll find this spectacular staircase mosaic .  (I do love staircase art!)  The detailing on the bottom two stairs reads: “Fiestas de la Calle San Sebastian 50 anos / Los 500 anos de la Ciudad de San Juan.” 

Old San Juan has so much fantastic street art, from murals to mosaics.  This makes it such a joy to explore all the nooks and crannies of the city.  Take your time strolling Old San Juan so that you don’t miss any hidden treasures.

34. Go for a walk in the park at Bahía Urbana

Along the edge of the harbor is the Bahía Urbana .  Long term, it will redevelop the waterfront area and transform it into a major tourist destination with high end shops and restaurants.  For now, it is mostly a beautification of the port area. 

If you head eastward from the Old San Juan Cruise Port Terminals, you can’t miss Bahía Urbana.  It announces itself with this large spiraling stone monument.  There are lots of arty chairs, shade areas, and water features along Muelle 6 (dock 6) heading towards this giant seahorse statue.

There is a pedestrian bridge connecting over to Muelle 8 (dock 8) which is a large park-like area with a carousel, an outdoor dining area, and public restrooms.

35. Take a selfie with the ‘I love PR’ sign

Yes, indeed, I love Puerto Rico !  And I’m willing to bet that you will too.  This sign is located along the waterfront right by the cruise ship docks for your easy photo op.

Old San Juan Attractions Map

With so many great things to see in Old San Juan, you might be having a hard time figuring out where the attractions are located. Here is a map of these attractions in San Juan to help you get your bearings:

If you prefer to have a downloadable map of these things to do in Old San Juan, check out this one:

Old San Juan Puerto Rico Travel Tips and FAQ

The best time to visit Puerto Rico is in the winter and spring, when the temperatures make for a great escape from cold winter climates. This is also the most popular time for Caribbean cruises to Puerto Rico. Puerto Rico is still quite popular in the summer, when temperatures are hotter.

The island of Puerto Rico is a US territory , so if you’re a US citizen, you don’t need a passport to visit!

The official currency in Puerto Rico is the US Dollar.

Spanish is the official language of Puerto Rico, with English being the second official language.  Do a little homework before your trip and brush up on a few common phrases in Spanish.  Easy phrases like ‘hello’, ‘please’, and ‘thank you’ go a long way in any foreign destination.

Puerto Rico is located in the Caribbean , and it is one of the islands of the Greater Antilles.  

Puerto Rico’s year-round temperatures are pretty consistent, with highs in the 80s and lows in the 70s. 

I hope you have enjoyed this whirlwind tour of Old San Juan as much as we did! And now you know exactly what to see in Old San Juan . 

There are some of the best things to do in San Juan Puerto Rico , and I hope that I have inspired you to visit!

Planning a visit to San Juan, Puerto Rico? Pin this for later!

You may also enjoy these posts on my favorite winter cruise port destinations in Mexico and the Caribbean:

• 11 Best Cabo San Lucas Tours: 5-Star Mexico Fun
• Best Camel Ride in Cabo San Lucas
• Best Things to Do in Puerto Vallarta: A Fun DIY Walking Tour
• 38 Fun and Easy Things to Do in Mazatlán
• 7 Best Dominica Tours and Shore Excursions
• Perfect Day in St Barts: Best Things To Do on a Walking Tour

Lisa Garrett

Lisa Garrett is the founder of Waves and Cobblestones. She has taken 18 cruises ranging from a multi-generational Caribbean cruise to solo Alaska cruises to fabulous Mediterranean cruises.

She lived in Ireland for 4 months and has taken over a half-dozen multi-city vacations in Europe (primarily relying on train and public transit). Lisa helps people plan amazing vacations to Europe and popular cruise destinations.

Learn more about Lisa !

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A Self-guided Walking Tour of Old San Juan

April 1, 2019

When planning our cruise to the Eastern Caribbean , there were many excursions to choose from at each port of call. We had already planned kayaking, snorkeling, zip line adventures, and water parks at our other ports and we were looking for something different to do in Puerto Rico. John had visited many years ago and suggested that we take a self-guided walking tour of Old San Juan.

Old San Juan Shore Excursion

The ship docked at the San Juan cruise port terminal, and we were able to walk into the old town from there. Consider a self-guided walking tour of these sites for your shore excursion instead of the usual offerings – it is a lovely day of wandering.

Upon leaving the Carnival Breeze , the bright colors were the first thing to catch my attention. Even though there were grey clouds and misting rain during our visit, Old San Juan is colorful, vibrant and has a real charm about it.

Where to eat in Old San Juan

Since it was raining when we arrived, we decided to have lunch first before exploring Old San Juan on foot. You’ll want to see Plaza Colón , a beautiful square with markets and a statue, so I recommend Cafe Berlin . Overlooking the square, it has a great terrace for people-watching; and serves delicious Puerto Rican food. I had the Ceviche and it was a real flavor pop!

Things to See in Old San Juan

I recommend that upon arrival at the cruise port, you walk north towards Plaza Colón . This walking tour will take you in a counter-clockwise direction around Old San Juan.

Castillo San Cristóbal

Castillo San Cristobal is the largest fortification built by the Spanish in the New World. In 1783, when it was completed, it covered about 27 acres of land and basically wrapped around the city. After nearly 100 years of peace, one-third of the fort was demolished to help ease the flow of traffic in and out of the walled city.

The fort served many purposes during its time and in 1961 the US Army moved out of the fort. It then became the jurisdiction of the United States National Park Service , to be preserved as a museum only.  

There are 3 levels at the fort.

• Level 1 is the main plaza and lowest level.
• The 2nd level is the main firing battery.
• Level 3 is the observation area and the highest level.

We explored them all, from the lowest of the dark tunnels to the highest hills above. Admission is free for children 15 and under and for adults it is $5.

Garita del Diablo

One of the sea wall fortifications of Castillo de San Cristóbal is Garita del Diablo. This bastion is right down by the ocean, and you have to walk through a graveyard to reach it. It is said to be haunted by spirits. Spanish soldiers used to be sent out on patrol here as punishment!

Old Fortifications

Upon exiting the fort, we chose to walk along part of the old wall that once protected the city. Payton enjoyed running around the open spaces along this coastal area. John and I spent a long time looking out over the Atlantic Ocean. You can see why the fortifications existed along this coast, Puerto Rico has so much coastline to invade!

There are several bastions along the north coast of Old San Juan. Bastión de Santo Tomás, Bastión de Ánimas, Bastión de San Antonio, and at the entrance to the San Juan Harbor, Castillo San Felipe del Morro. San Felipe del Morro is a 1-mile walk from Castillo San Cristóbal, and the nearby Panoramic overlook has a good view back towards where you’ve just walked.

Old Town Shopping

Had enough of fortifications? Time to weave your way through the streets of the old town for some shopping!

Weave your way south down Calle del Cristo, and then east along the great shopping street of Calle de la Fortaleza.

If museums are more your thing instead of shopping, there are a few in the upper left quadrant of Old San Juan. Museo de las Américas – a museum of pre-Columbian and modern art from the Americas. Casa Blanca , a museum in a beautiful estate, built in the 1500s for the Spanish conquistador, Ponce de León.

Or learn more about the local people at the Institute of Puerto Rican Culture . Built in an old convent, it is definitely an interesting place to visit. Not far from there is the Museum of Art and History , which is housed in an old market building with an internal courtyard.

Needless to say, there is more in Old San Juan than can be seen or done in 1 day of shore excursion. So, pick what suits your tastes on this self-guided walking tour of Old San Juan.

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Old San Juan Parks

The joy of a self-guided walking tour is that you can stop when you need to. In the summer, the many lovely gardens and coastal breezes will help you cool down. Payton loved Parque Las Palomas on the south coast of Old San Juan. It has beautiful scenic views, and A LOT of friendly pigeons. I don’t think we’ve ever seen so many. Relax and feed the birds at this park, but maybe don’t try and eat a sandwich – they might steal it!

Walk back towards the cruise port via Paseo de la Princesa, this manicured promenade has fountains, cafes and shady spots to get out of the sun.

Interesting Fact : If you have ever visited Savannah, Georgia, then you know about the cobblestones that make up River Street downtown. Here, in Old San Juan, they have cobblestone streets as well, but they are blue! These bricks were cast out of the remains of the iron-refining process. The moisture of the iron gives them their deep blue color. Legend says that if you listen closely, you can hear the footsteps of the Spanish soldiers who once walked the streets.

See more of our Caribbean cruise adventures in Amber Cove , the US Virgin Islands , and Grand Turk !

We really enjoyed our day in Old San Juan, Puerto Rico while cruising with Carnival. I would recommend taking some time to explore all that is there. The colorful city, the historical forts, and the vast views of the Atlantic Ocean are all worth the visit. From the cruise port, everything we experienced was within a 20-30 minute walk from the port. Perfect for a self paced walking tour!

Have you visited San Juan? If so, what was your favorite spot?

Let us help you plan your cruise to Puerto Rico, with our full service Travel Agency !

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4 thoughts on “A Self-guided Walking Tour of Old San Juan”

It’s officially on my list!

It’s officially on my list! Thanks 🙂

Beautiful pics…PR is on my list and this post wants me to bump it up on my list. Thanks for sharing!

The pic with the suspended umbrellas remind me of some of the streets in Italy. Puerto Rico is a wonderful cruise port with tons of activities. Old San Juan particularly is classic. Great pics!

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San Juan Drive Around Food Tour™

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• Tags Category: Driving Food Tour

When: Thursday, Friday & Saturday Morning.

Duration: Approximately four (4) hours

Group Size: 6 guests minimum/ 12 guests maximum

Meeting Point: San Juan (exact meeting point provided with booking confirmation)

Attire: Comfortable shoes and light clothing (the van is air conditioned, but some of our stops are outside)

Tours take place rain or shine!

Off the beaten path culinary & cultural experience!

On this driving culinary tour , you’ll get a real off the beaten path experience and feel like a local. Hop into our Spoon van and explore up-and-coming neighborhoods, enjoying scrumptious local spots along the way. We designed this immersive tour to give our guests the chance to discover hidden treasures throughout the areas visited.

Your epicurean guide takes you on a gastronomic adventure, digging deep into the history of the ingredients and cultures that make up Puerto Rican cuisine today. Learn about mangoes, plantains, and local peppers; sip on rum and coffee all while savoring tasty dishes at unique locales.

On our San Juan food tour, you’ll visit  Calle Loíza , a revived gastronomic hub,  Santurce , a culinary, arts, and music district, and Piñones, a neighborhood deeply rooted in African tradition all while tasting along the way. This guided, narrated food tour is both a cultural and culinary experience. You also learn about the history, architecture, art, and people of the communities visited.

SPOON is firmly committed to reinvigorating Puerto Rico’s economy and agricultural heritage. By frequenting small, independently owned establishments that use local, sustainably-sourced ingredients , we bring you the best and help our beautiful island thrive. Our experiences are kept small in number to ensure that you don’t get tourist trapped. You’ll enjoy the full attention of our guides and walk away with the best advice of what to eat, see, and do throughout the course of your stay. Whether your traveling solo, with friends and/or family, you’ll soon see why touring with SPOON is one of the best things to do in Puerto Rico.

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Old San Juan Walk & Taste Tour™

Walk at a relaxed pace along the historic cobblestone streets during this Old San Juan food tour and use gastronomy, history, and architecture as a passage to discover Puerto Rican culture.

• Clock Afternoon

Sunset Walk & Taste Tour™

Our afternoon guided walking food tour lets you experience Old San Juan like a local. You’ll taste several dishes, including two alcoholic beverages, and stop at major points of interest along the way. It’s a food, drinks, history and culture tour all in one!

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Travel Itineraries , North America , Travel Destinations , Travel Tips

24 hours in san juan: the perfect one day itinerary.

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Having only 24 hours in San Juan isn’t necessarily ideal (it’s way too beautiful there and I could stay forever). Don’t despair, though! Even with limited time, you can still see and do a lot in a single day.

As an Caribbean island, Puerto Rico is very popular for many reasons. Americans don’t need to bring a passport, for example, and plenty of direct flights depart the United States each day.

In addition to its natural wonders, San Juan’s vibrancy is a huge draw in and of itself. I fell in love with this city as a solo traveler. There are so many things to do alone in San Juan that I could’ve stayed forever.

Furthermore, San Juan is a starting point for many popular cruises. Luis Muñoz Marín International Airport also has several flights that connect to other islands that may not have direct routes from the United States. It’s not uncommon to do a long layover here, before departing for other Caribbean destinations. 

So, as you can see, there are many reasons why travelers might only have a brief stop in San Juan. 

Don’t despair, though. You can still see and do a lot with 24 hours in San Juan, but (unsurprisingly), it’s still important to wisely manage your time. 

Table of Contents

24 Hours in San Juan: Practical Advice

First I wanted to share a couple of practical suggestions, before going into more detail regarding this 24 Hours in San Juan Itinerary.

Over all, San Juan is a very easy travel destination, especially if you have travel experience under your belt and speak a bit of Spanish, but it’s still better to be prepared. Just in case! 

Transportation to San Juan 

Most travelers will arrive at Luis Muñoz Marín International Airport. This airport is very centrally located. I’m not exaggerating when I say that most San Juan hotels are a 15 minute car ride away, which is fantastic. I know it certainly made arriving at 1 am. a little more bearable for me. 

Upon arrival, I would just let other people handle the transportation logistics for you. 

For instance, I don’t personally recommend renting your own car for your stay in San Juan. Parking is a nightmare in Old San Juan, and rideshares are so readily available that a car would just be an expensive hassle. 

Download Uber to efficiently get around town. 

What to Bring for One Day in San Juan 

Whether you only have a single day in San Juan, a longer trip around Puerto Rico, or a Caribbean cruise, you will want to be adequately prepared for tropical weather. 

Here are a couple of essentials for your 24 hours in San Juan.

• Bathing Suit: Okay, I know you only have a day, but still. You’ll want to go into the water in San Juan. Whether you’re swimming in a pool or kayaking, don’t forget a good bathing suit! 
• Bug Spray:  Bugs are super annoying and you don’t want them to bother them on your trip. Pack a small bottle of bug spray as an additional precaution. 
• Comfortable Walking Shoes: Old San Juan is gorgeous, but the cobblestones will legit destroy your feet if you wear crappy shoes. Ditch the strappy heels and go for a solid pair of walking shoes that you’ll appreciate once you’re out and about. 
• Day Bag:  A lightweight day bag is really all you need for exploring San Juan. As a FYI, I had no issues with pickpockets or safety in San Juan, but at the same time, I understand that some travelers want a bit of extra protection. Bring a crossbody Pacsafe bag for the extra peace of mind. 
• Sunglasses:  Without question, sunglasses are very important to keep your vision pristine while you wander the streets of Old San Juan and beyond. You can find many affordable sunglasses to take with you if you don’t want to spend a ton of money. 
• Sunscreen: You don’t want sunburn to be one of your souvenirs in Puerto Rico. The UV rays are very strong here, especially at the hottest times of the day. Make sure to pack high quality, environmentally friendly sunscreen to stay safe as you sightsee around San Juan. 
• UBF Clothing: So, not to be a jerk, but let me repeat myself … Don’t mess around with the hot sun in San Juan. For even more precautions, pack clothing with UBF protection that will keep your body safe from the sun’s rays. Even though they’re a little expensive, Coolibar makes great quality clothing that’s perfect for San Juan including this fun sundress tunic and these gorgeous white wide leg pants . Explore their line for pieces that fit your style. 

Where to Stay in San Juan 

For a short visit in San Juan, I recommend staying either close to the airport or Old San Juan. This will make your next day departure a lot easier to handle. I’ve listed a couple of suggestions to get you started on finding accommodation. 

• Caribe Hilton:   The home of the original frozen Pina Colada (supposedly), Caribe Hilton has a great pool and beach, and also is very close to the airport, making a great choice for one day in San Juan. See prices on Expedia.com and Booking.com  
• Candado Vanderbilt Hotel:   If you want to splurge, then you ought to check out Puerto Rico’s first luxury hotel, which was opened in 1919. This resort is only five miles away from the airport. See prices on Expedia.com and Booking.com
• DREAMCATCHER By DW:   Looking for something a bit smaller but still wonderful? DREAMCATCHER by DW is the perfect little boutique hotel that’s only a block from the beach. See prices on Expedia.com and Booking.com

What to Do in San Juan in Only 24 Hours

Not sure what to do with 24 hours in San Juan?  I completely understand. Whenever I research a new travel destination, I easily feel overwhelmed at all the attractions and restaurants and cool neighborhoods, and always end up trying to see too much in a limited time. 

Short itineraries are tough.

Admittedly, even though I narrowed down my ideas, I still feel like I’ve listed a lot of options in this one post. So, feel free to edit some items out, or if you’re a super active traveler, then maybe this itinerary will work for you. Live your truth. 

Either way: I hope you have a wonderful time even with only 24 hours in San Juan. 

Explore Old San Juan 

Old San Juan is home to cobbled streets, colorful homes, trendy boutiques, historical sites, and so much more. Although touristy, I believe no visit to this city is complete without a leisurely stroll around Old San Juan. I could’ve hung out here forever. It’s so cute. 

Old San Juan is confined to a reasonably small and walkable area, so once you arrive, you don’t need to worry about driving again for awhile. I know I already talked about car rentals, but I feel like it bears repeating: I actually wouldn’t recommend having your own car, because parking here is a bit of a … nightmare, to say the least, especially when there are construction projects. 

For those of you interested in history, I would suggest taking an organized San Juan Walking Tour to maximize your time. San Juan’s history is incredible, and I feel like it’s important to learn about the places that you’re visiting.

Whatever you do, don’t miss Calle de la Fortaleza or the umbrella street! It’s so pretty! I don’t even think Instagram does it a justice, haha. 

As a side note, I felt like travel in Puerto Rico was very safe , particularly in Old San Juan. You can pretty much wander everywhere (except La Perla) and not feel worried about your personal safety – which is a nice bonus. 

Visit Castillo San Felipe del Morro

Castillo San Filipe del Morro offers some of the most iconic views of San Juan.  This historic citadel is run by the National Park Service and strategically overlooks the entrance to San Juan Bay. Take plenty of photos. 

The citadel is reasonably big, but not overwhelming either. I think I spend about an hour and a half here, and felt like I saw everything without rushing. 

My one piece of advice is to go to Castillo San Filipe del Morro early in the day. It gets hot and humid inside the citadel, and although some rooms have fans, sightseeing later in the afternoon might be uncomfortable for some travelers. 

And don’t forget to see families flying kites on the expansive lawn! Flying kites is very popular in this area, and some of them are very beautiful. 

Eat as Much Delicious Puerto Rican Food as Possible 

Puerto Rican food is literally the best thing ever. It doesn’t matter if you have only 24 hours in San Juan. It doesn’t even matter if you only have five minutes in San Juan. You need, need,  need  to eat some Puerto Rican food. Come to San Juan on an empty stomach. 

Do your research ahead of time, and pick a couple local restaurants to enjoy. Do not go to chains in Old San Juan, haha. Eater has a great restaurant guide that will help you plan your food adventure. 

However, if you’re a major foodie and want to try as much as possible, then I suggest booking yourself on an organized food tour to maximize your time in San Juan. The guide will take you to a variety of places, so you’re able to sample a bunch of delicacies. 

Take a Rum Tour

You can’t spend 24 hours in San Juan and miss out on a rum tour (I mean, unless you don’t drink, in which case, spend extra time outdoors). However, huge rum fans will appreciate a visit to Casa Bacardi. 

Casa Bacardi is technically outside Old San Juan, but rideshares and tours are frequent enough to make a visit possible on a one day trip. I think it took about twenty minutes for me to go from the Caribe Hilton to Casa Bacardi. 

At Casa Bacardi, the guided rum tasting tour will take you through the brand’s history. You will also receive a free drink and sample a variety of rums, including a special one that’s only produced in Puerto Rico! The guides are entertaining and informative too.

On a pretty day, don’t forget to enjoy your free welcome drink at the expansive outdoor bar. 

Go for a Swim (or Do an Outdoor Activity) 

Okay, I know you can be lazy in the pool anywhere in the world, but I need to build a break into every itinerary. Take advantage of a pool or a beach in San Juan, and simply relax. 

Even an hour of relaxation makes a big difference in your own. 

Of course, you’re also welcome to seek out more active outdoors adventures, such as kayaking, but me personally, I love the pool. Love, love, love. 

Keep in mind that San Juan may have a couple of beaches, but Puerto Rico’s most beautiful beaches are located elsewhere on the island. Sure, you’ll enjoy plenty of sweeping and blue bay views, but beach seekers shouldn’t have super high expectations, especially with only 24 hours in San Juan. 

Plan a Cocktail Crawl & Enjoy the Nightlife 

I can’t talk about San Juan without including a nightly cocktail crawl. Your 24 hours in San Juan are slowly coming to an end. Why not close out today with a bang? 

San Juan is known for having an incredible cocktail scene. Even if you don’t drink, a mocktail Pina Colada tastes like a rich (and delicious) dessert that you’ll savor once your trip has officially come to an end. 

In many ways, the bars themselves are huge attractions worthy of a visit in their own rights. For instance, La Factoria is one of the most famous bars in the Caribbean (and the world). It’s so much fun exploring the different bars and sampling the drinks. Obviously, La Factoria gets crowded, so arrive early to ensure you have a seat somewhere. 

Of course, there are a ton of other wonderful bars to choose from. Casa de Montecristo, for instance, is a relaxing cigar bar that’s perfect for unwinding after a busy 24 hours in San Juan.

24 hours in San Juan in definitely doable. I hope this guide gives you plenty of ideas of how to best spend your time in San Juan. Don’t worry, though. I’m sure you’ll be back again soon. It’s super easy to fall in love with this magical island. 

Rachel Elizabeth

At 22, I took my first overseas trip to Bermuda. Took a break to follow the "American Dream." Had my self-esteem broken. Embarked on my first solo trip to Scotland at 26. The travel bug dug its way under my skin. I now book multiple trips a year.

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Top 13 Must See Things to Do in Old San Juan, Puerto Rico

Published: Feb 3, 2024 Modified: Feb 3, 2024 by Karen Kelly

Are you looking for things to do in Old San Juan during your next trip to Puerto Rico?

You can enjoy the city when visiting old San Juan for a day, but there is so much to do you might feel you missed out on part of the experience.

On my last cruise to the Caribbean, Old San Juan was one of my favorite stops. The vibrant colors, delicious food, and historical landmarks were stunning. The San Juan cruise port was an afternoon/evening stop. Although my friends and I saw a lot of the city, I want to go back to experience more Old San Juan has to offer.

For your itinerary, look at the activities in Old Town Puerto Rico and narrow it down based on your interests and some travel tips highlighted below.

You might prefer visiting one of the forts in Old San Juan with awe-inspiring ocean views or enjoying the vibrant nightlife with dancing and Piña Coladas. Whatever your preference, San Juan has something you’ll enjoy.

Photo Credit: Deposit Photos

Top Things to Do in Old San Juan

Old San Juan used to be named “Ciudad de Puerto Rico,” meaning the City of Puerto Rico. The city has a rich history involving the Spanish colonial government. 

The preserved old colonial vibe makes unique things to do in Old San Juan, Puerto Rico. You can explore a Spanish fortress or enjoy a San Juan walking tour of the city through its blue cobblestone streets.

If you’re visiting Puerto Rico from the United States, you don't need a passport since it is an unincorporated territory of the United States.

Whether you are stopping by on a cruise ship or planning to stay at a resort, there are many fun things to do in Old San Juan.

Photo Credit: Katie Restrepo

1. Colorful streets of Old San Juan

One of the things to do in Old San Juan for free is to walk around. 

Sure, you can join a guided tour- and I’ll highlight a few later- but the charm of this old city is all around you.

Take in the colorful buildings while you walk along the blue cobblestones. 

My friends and I saw a cobblestone street in the process of being repaired during our visit. It was so cool seeing this old-fashioned way of making streets in Old San Juan being preserved. It was like walking back in time.

The more you walk through the rainbow buildings, the more you’ll find great Instagram-worthy photo ops. There are balconies with flowers and street art that pop out at you. The brightly colored walls are a perfect backdrop to record your adventures.

Bonus: it’s one of the free things to do in Old San Juan. A vacation in the Caribbean can add up, but some islands are cheaper than others .

2. Castillo de San Cristobal

Do you want to continue walking into the past? Then you must visit Castillo de San Cristobal. The fortress is a popular attraction in Old San Juan and is only a 10-minute walk from the cruise terminal in Old San Juan's harbor.

Part of the San Juan National Historic Site, Castillo de San Cristobal is a fortress built by the Spanish to protect against attacks by land.

Fun Fact: This fortress gets its name from Saint Christopher, the patron saint of land travelers.

The 27 acres of Castillo San Cristobal make it the largest fortress the Spanish built in the New World. 

You can explore the dungeons, tunnels, and ramparts on your own or through a ranger-led tour. Check out the “Garita del Diablo,” or Devil’s Sentry Box, where legends say multiple soldiers mysteriously disappeared.

If you're not a history person, you can still take in amazing views of the ocean and the city of San Juan. 

3. Castillo de San Felipe del Morro

Another of the best places to go in Old San Juan is Castillo de San Felipe del Morro . The fort is a little further away but worth the 30-minute walk (it only took my group 15 minutes, but we are fast walkers) from the cruise terminal.

The purpose of Castillo de San Cristobal was to defend San Juan from invaders by land. Castillo San Felipe del Morro protected the city from invaders by sea. 

El Morro and Castillo San Cristobal are both impressive military forts of Old San Juan, but I prefer El Moro if you have to choose one to tour.

When you walk up to El Morro, you are greeted with large green lawns. It was a little too windy for me (my hat kept flying off), but it was perfect for flying kites. 

We stopped at an ice cream cart nearby before going into the fortress. I can never pass up ice cream, especially passion fruit-flavored ice cream!

Similarly to Castillo de San Cristobal, El Moro has dungeons, ramparts, canons, and all sorts of fortress nooks and crannies to explore. Fair warning- there are a lot of stairs, but the panoramic ocean views are worth every step.

Paseo del Morro is the boardwalk going around the fortress and eventually merges with Paseo de la Princessa.

4. Paseo de la Princesa

If you’re looking for something less fort-centered and more romantic, take a walk along the Paseo de la Princesa. 

Start or end your walk of Paseo de la Princessa at the San Juan Gate. The walkway has old-fashioned street lamp posts with sweeping views that overlook the bay of San Juan. Fountains and gardens line the path.

  The San Juan sunset is stunning over the water. After a romantic walk on land, you can book a sunset boat tour.

Try eating at the Princesa Cocina Cultura restaurant for a fancy, romantic dinner. They offer a "real Puerto Rican gastronomy." Don’t worry- gastronomy is a good thing. It’s the art of cooking and eating good food.

Weekends are full of street vendors and performers along this historical pathway. If you have kids, they’ll love the live music and the Paseo de la Princessa playground.

If this sounds like your type of activity, book a walking tour of Old San Juan . 

5. The Governor’s House, La Fortaleza 

One of the National Heritage Site landmarks you’ll walk by on the Paseo de la Princesa is the Governor’s Mansion, La Fortaleza.

Take a guided walking tour of the Governer’s House rooms and gardens. Just check their website to see if it’s open to the public during your stay.

The street leading up to the Governer’s House is Fortaleza Street. It is the oldest street in the area and offers all kinds of shops, restaurants, and hotels.

You might recognize Fortazela Street as the one with colorful umbrellas over it. Sometimes the umbrellas are replaced with other art or the Puerto Rican flag, but it’s still a beautiful art display you can’t miss. 

When I visited, the umbrellas were rainbow. My group couldn’t walk under the umbrellas since the street was closed to passers-by, but we could still get a great picture!

6. Eat, Eat, and Eat

Deaverdura on the corner of Sol St and Calle de la Cruz in Viejo San Juan is a must-try. It’s an Old San Juan restaurant, and their traditional Puerto Rican food was absolutely worth the 30-minute wait for a table. 

The “pernil” (slow-roasted pork) was so tender and full of flavor. I also got the sampler platter with my friends, which was more than enough for all of us with the “pernil” and rice. The platter came with fried yucca, “morcilla” (blood sausage), and “tostones” (fried plantains).

The old city is also famous for its food trucks. If I hadn’t filled up on food from the restaurant, I would have stopped to buy from the San Juan food trucks on the walk back to the cruise ship.

If you’re a foodie , don't leave Puerto Rico without trying mofongo. It’s fried plantains mashed up with “chicharrón” or pork rinds.

You can book a food tour so you don’t miss any Puerto Rican food highlights!

7. Enjoy a Rum Tour and a Piña Colada

Puerto Rico is one of the best Caribbean islands to visit for its history and food, but it’s also well known for its drinks.

Did you know that the Piña Colada was created in Puerto Rico? The story says a bartender at the Barrachina restaurant invented the Piña Colada. 

If you don’t have time to make a reservation at Barrachina, you can walk up to their courtyard bar and order a Piña Colada. They even offer small cups of virgin Piña Coladas for kids if you’re traveling with family. The legend holds up because it was the best Piña Colada I’ve ever had.

San Juan Rum Tours are also popular, and this 75-minute Rum Tasting Tour takes you to the world-famous Casa Bacardi. You’ll taste many different styles of Bacardi rum and get a tour of the distillery.

Food, drink, and dancing are the top things to do in Old San Juan at night, so after your tour, check out more local businesses as you explore the city.

8. El Yunque National Forest

If you like more outdoor adventures like hikes and waterfalls, then don't skip El Yunque. 

El Yunque is the only rainforest in the U.S. National Forest system and is only a 40-minute drive from Old San Juan. I skipped this on my visit to Old San Juan because it would have taken up most of my afternoon/evening cruise port time. 

Pick a hike and explore on your own, or choose from multiple tours that focus on everything from adventure, wildlife, and nature walks.

You can see amazing views from the Mount Britton Tower or swim in the natural pools below La Mina Falls.

A full-day tour of El Yunque picks you up from your hotel or the cruise terminal. The tour includes hiking to waterfalls and natural pools. 

You can even slide down natural waterslides and have fun on rope swings and cliff jumping. Start at 8:00 am and end after 4-5 hours with lunch at the famous Luquillo Kiosks at Luquillo Beach before returning to your Puerto Rican resort .

9. Capilla del Cristo

Not into hiking or cliff jumping? Tone things down a bit with a visit to Capilla de Cristo, the Chapel of Christ.

This chapel was created in the 1700s and has beautiful architecture. The coolest thing is the miracle. Legend has it that a horse race ended with a rider and horse falling off the nearby cliff. The rider survived, and the chapel was made to commemorate the miracle.

If you’re into art, check out the famous painting by Jose Campeche, a famous Puerto Rican painter, inside the chapel.

Enjoy looking out at the bay from the Capillo del Cristo, then check out the Plaza de Armas next door. The Plaza de Armas was the main town square where soldiers gathered. Plaza de Armas is now known as the heart of Old San Juan and is often full of music and dancing.

10. Casa Blanca

The history behind Casa Blanca and the other monuments, buildings, and fortresses make Puerto Rico a World Heritage Site.

Close to the fortress El Morro, Casa Blanca was the first building in San Juan, Puerto Rico. The White House was built for the Governor, Juan Ponce de León, and his family. 

Juan Ponce died before he could move in, but his family was able to live there. The Spanish Army and then the American Army occupied Casa Blanca.

Casa Blanca is now a museum with relics from the 16th and 17th centuries. You can still see what the rooms were like for those who lived there while enjoying a view of San Juan Bay.

11. Shopping in Old San Juan

You can’t enjoy a Puerto Rican vacation without buying a souvenir. There are shops everywhere so you can easily stop to shop while walking around to the tourist activities.

  The shops and restaurants are all intermingled along the city streets. You’ll find a mix of name-brand companies and mom-and-pop storefronts. Browse for clothing, jewelry, perfume, art, and so much more.

One of the most unique (and delicious!) stores I like is Chocobar Cortes. They have a variety of chocolate products, including cacao wine. It’s perfect for finding a unique gift for a chocolate-loving friend back home.

The Poet’s Passage is another fun shop with original poetry and art made from those poems.

12. Catedral de San Juan Bautista

If religion or beautiful stained glass windows in a cathedral with beautiful architecture are more your speed, then check out the San Juan Cathedral on your visit to Puerto Rico.

Juan Ponce de León, the first Governor of San Juan, who didn’t get to live in his Casa Blanca mansion, was buried at the Catedral de San Juan.

The cathedral blends Gothic and neoclassical architecture and has been refurbished over the centuries.

Fun Fact : The San Juan Cathedral was built in the 16th century and is the first church built on U.S. soil.

13. Rogativa Plaza

The best 180-degree view overlooking San Juan Bay has to be from Rogativa Plaza.

It’s a beautiful, historic plaza where you can see the El Yunque forest, La Fortaleza, Isla de Cabras, and the San Juan Gate. Just walking along the path by the city wall gives you the full historical vibe of Viejo San Juan.

The famous statue, "La Rogativa" is a statue of a Bishop leading a procession. The statue is at the plaza's center and represents the precession that scared off the British invaders.

I guess they took one look at the hundreds of torches and aborted their mission because they thought the torches were military reinforcements. 

Summary of Best Things to Do in Old San Juan, Puerto Rico

With so many things to do in San Juan, Puerto Rico, I recommend walking around Castillo de San Felipe del Moro. In my opinion, it has better ocean views than its sister fortress, Castillo de San Cristobal.

Try the local cuisine during your visit. I would get “pernil” (pork) from Deaverdura and a Pina Colada from Barrachina.

If you have a full day to explore, take a fun waterfall adventure tour in the El Yunque rainforest followed by lunch at the famous Luquillo Kiosks on your way back to Old San Juan.

Whether you’re enjoying Puerto Rico travel as a family, finding yourself on a solo trip, or enjoying a vacation with friends, Old San Juan is a must for your itinerary. 

What activity would you choose first?

Karen Kelly

Hi, I'm Karen Kelly a certified health coach, freelance food and travel writer, and blogger. At Seasonal Cravings, you will find delicious recipes and fun travel ideas.

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December 21, 2023 at 12:29 am

Great job Karen for the writing about Puerto Rico. particularly Old San Juan. 👏👏👏👏👏⭐⭐⭐⭐⭐

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Puerto Rico Private Tours

Old San Juan Historic Driving/Walking Tour

Pick-up time & location :, we pick you at the doorsteps of your hotel or home. tour start time is completely flexible., duration: 4-5 hours, all of our tours are private and the duration of them is completely up to your group, from our experience most san juan tours take 3 to 4 hours but it is not uncommon for tours to stretch 5 to 6 hours if both of the major forts in san juan are explored and some shopping time is added., tour description:, discover the atmospheric streets, amazing architecture and intriguing history of the second oldest european settlement in all of the americas, a truly unique experience san juan is considered one the best preserved spanish colonial cities , boasting layers of unique architecture ranging from the medieval gothic style of the san jose church, to the neo classic façade of the late colonial period. while the city's building make it a unique and grand spectacle, it is the people of san juan who will make you feel at home, join us for a taste of traditional puerto rican coffee, limber frozen fruit treats or a hearty meal of mofongo and churrasco and discover your new home away from home., our tours feature a mix of walking and driving portions, our guides will inquire as to which areas you would like to explore best on foot, they will also recommend stops at some of the major landmarks of the city. our tours are built around you and your group, if you prefer to tour the city by driving only or if you would rather explore most of the city by foot just notify us while booking your tour and your tour guide will be ready with a tour itinerary catered to your exact needs. our competitive hourly rates include pick up/drop off at your hotel or place of lodging and cold bottled water ., among the many sites visited:, * el morro (castillo de san felipe del morro) * san cristobal fortress * capitol building, casa de españa and the city wall * plaza de armas (arms square) * plaza colon (columbus square) * san juan cathedral, pricing: all of our tours are private and are priced per hour , depending of the vehicle size, not per person,  please call us at 787-918-7748 or click here for exact pricing, book your san juan tour:, book easily by calling 787-918-7748, or select the old san juan tour option on our online booking tool accessed by clicking here .

El "Yunke" Rain Forest, Surrounding Areas Tour

We pick you at the doorsteps of your hotel or home. tour start time is completely flexible. (in order to avoid crowds we recommend being picked u at your hotel between 7:45 and 8:30 am), duration: 4-7 hours (including travel time), all of our tours are private and the duration of them is completely up to your group, depending on the number of waterfalls, trails and other attractions you choose to visit while in the forest the tour can range between a quick sightseeing/picture talking outing of 4 hours to an extnsive outing covering all of the east coast of the island. , while most of the rain forest remains closed due to the passing of hurricanes maria and irma, our tour now includes the surrounding areas that were least affected by the passing of the hurricanes., finally while moving from one attraction to the other enjoy the scenery from our luxurious mercedes benz sprinter vans, with huge window areas and a comfy ride; we pride ourselves on having the best tour vehicles to go along our excellent tour guides., among the many sites visited are…, * las pailas, natural water slides * la frutera, the legendary tropical fruit smoothie spot * loiza scenic coastal road, pricing: all of our tours are private and are priced per hour, depending of the vehicle size, not per person, please call us at 787-918-7748  or click here for exact pricing: , book your el yunke surrounding areas rain forest tour:, book easily by calling 787-918-7748, or select the el yunke rain forest tour option on our online booking tool accessed by clicking here .

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Getting Around Guide for Cruise Visitors San Juan, Puerto Rico

Puerto Rico ⎮ San Juan ⎮ San Juan Cruise Guide ⎮ Getting Around from the Cruise Piers

Photo: San Jose Church – Old San Juan, Puerto Rico

Save a Spot - Most Popular Walking Tour

One of the most frequent questions for cruisers is regarding getting around.  From the Old San Juan Piers , you can simply walk to the historic district to enjoy most of the attractions, museums, shops, restaurants, scenic walkways, and cultural experiences.  If your ship stops at the Pan American Pier , you will need a taxi.  

There are many great tours you can choose from local enthusiastic and friendly operators that have put together great itineraries so visitors can make the most of their time during their cruise stop, we have listed them below.  Some cruise ships offer tours, however, you may wish to compare prices, since often they cost more than booking with local operators, most can be booked ahead and paid later, and they’re easy to cancel if needed.

Exploring by Foot

Photo: Paseo de La Princesa – Old San Juan, Puerto Rico

Old San Juan – The historic district of Old San Juan is a very walkable city, keep in mind the streets are narrow going uphill, we recommend you wear comfortable footwear.  Going to the forts you’ll have to walk uphill a little, but for the average person is not difficult.  Various excellent walking tours are available to make the most of your time in Old San Juan.  Please read “ Visiting Tips ” in the Old San Juan Guide. 

Condado – The tourist district of Condado is also walking-friendly, but you’ll need a taxi to get there from the pier.

Top Rated Walking Tours in Old San Juan

+ Tours in Old San Juan

Taxis & Private Transfers

• Taxis: You’ll see plenty of taxis by the cruise port; the rates are set, and you’ll see them posted on the taxi/van doors.
• Private Transportation:  If you want a more personalized experience and have special needs, the driver will arrange the meet-up point that’s convenient for you.  See private transportation / transfers below.

+ Popular / Budget Friendly Private Transfers

+ luxury transfers, + shared / lower coast transfers, + large group luxury transfers, private driving tours, old san juan trolley.

The Old San Juan trolley is not currently in operation.  If you have special mobility needs we recommend you take a look at the private and driving tours our local friendly guides offer.  Feel free to express your needs, Puerto Ricans are known to go out of their way to accommodate visitors’ wishes.  See below for private tours.

+ Old San Juan Trolley

There are private driving tours, and we recommend them for visitors with mobility challenges or visitors that wish to enjoy Old San Juan suited to their needs and only their group.

Exploring by Bike

There are bike rentals to explore the tourist districts of San Juan.  Old San Juan has scenic routes perfect for riding bikes, however, be aware that the streets of Old San Juan are narrow and the sidewalks are only wide enough for pedestrians.  Puerta de Tierra and Condado have designated bicycle routes.

Bicycle Rentals in San Juan

Renting a car near the cruise ports.

Just a day in San Juan as part of your cruise itinerary?   If you’re arriving in San Juan on a cruise and you only have a day, renting a car may not be the most convenient option.  You may consider hiring a tour operator or private transportation to take you to interesting places around San Juan.  You will pay some extra money, however, you won’t have to worry about logistics or much planning.

Extending your stay?   If you’re staying a few days in Puerto Rico before or after your cruise, having a car rental gives you the most freedom to experience the island.  With some planning, you can enjoy some great attractions by getting behind the wheel.

+   Car Rentals near San Juan Cruise Ports w/ Map

Puerto Rico Tourism ⎮ San Juan ⎮ San Juan Cruise Ports Guide ⎮ Getting Around from the Cruise Piers

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January 4, 2024

Airport Transfers – Luis Munoz Marin International Airport “San Juan Airport” (SJU) to Hotels & Nearby Tourist Destinations

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Zip Around Old San Juan on a Segway

1/21 Segway Tours are open and offering tours!

People always ask about the best way to tour Old San Juan. Should you take a taxi, the free trolley , or just get in your car and drive around, or what? We always tell people that the best way is to walk around the city on your own . The old city isn’t really so big that it can’t be covered on foot. Besides, you’ll miss a lot if you’re driving in the streets, and you’ll most likely get stuck in traffic and waste a bunch of time. We recently heard about another option … a Segway tour. OK … So you’re asking "What the heck is a Segway?" A Segway is a two-wheeled, self-balancing, electric, personal transportation device . Huh? Take a look at the photo. You’ve probably seen them at the mall or being used by city police. You’ve probably pointed and laughed at the funny looking machine. Ever since they came out, riding a Segway was one of those things Ray always wanted to do. Kind of geeky, I know! When we would see the security people in the malls riding around on them, we would wonder where we could try them. When we found out about the Segway tours offered right here in Old San Juan, we knew we had to give it a try. They’re located next to the ferry terminal on the waterfront. That’s real convenient for anyone visiting the old city, especially if you’re on a cruise ship that is docked right there. So this past week we had some free time to "play tourist". We contacted Segway Tours of Puerto Rico , made a reservation for their 2-hour tour and off we went to Old San Juan.

The Training

We stopped by their office when we first got to town to say hello and just to make sure we were still "on" for our 3:00pm reservation. When we got there, we met Jose, Natalie and Geraldo who own the operation. Since they were between tours, and we had some time to kill before lunch, we opted to get our Segway training at that time. First, Jose hops on a Segway and starts zipping around in their little office. Forward, backward, turning in tight little circles … he makes it look real easy and fun. Then they explain the Segway, how it works, a little bit about the technology (it has a computer and gyroscopes inside), and how it self-balances and won’t let you tip over. Then it’s your turn to try. After they put you through the "step on, step off, go forward, go backward, turn left, turn right" drill, they have you navigate through their doorway and out onto the sidewalk, where they have you practice going up and down slopes, over some small bumps, and turning corners. All in all, the training only takes about 10 or 15 minutes. The whole time, one of them is right there by your side while you find your center of balance. At first it is weird and you feel all wobbly on the Segway. But after a few minutes, you feel pretty good about it. It is just kind of odd. It not like a skateboard, or skis, or roller skates. It’s like no other transportation device you have ever used. You can turn on a dime, go forward and backward with just a small movement of your body. A slight lean this way or that will move you around town. All you need to be able to do is balance and watch how close you are away from things. Once you find your center of balance, the machine does most of the balancing for you. I honestly felt it was really easy, and getting off was the most "difficult" thing about it. And all that really requires is a slow steady step straight back and down. So now that we were trained "experts", off we went to eat lunch.

Out on the Open Road

After killing some more time in Old San Juan, we returned to their office for our tour, and, as it turned out, the other people on our tour had to cancel, so we got a private tour with Jose. They gave us sunscreen to put on our faces and arms (very important!) and away we went!

Jose was very knowledgeable about the old city, and he is very personable too, so we felt very comfortable with him. Safety is always a concern (for their clients and their Segways), so you travel on less-congested routes and walkways. As I said, I was a little wobbly at first after the training, but after a few minutes of riding during the tour, you forget all about the "how to do it" and it just comes naturally. I think that going through the forward-backward-turn-turn-off-on drill, though it shows you the basics, is unnatural and a bit stressful. Once you’re cruising along at 5 MPH your stops and turns are more natural, and not happening in rapid secession.

The 2-Hour Tour

We opted for the two-hour tour, which makes a number of stops at historical places along the route. All along the way, Jose explains you what you are seeing and what it’s significance is. We went along the waterfront, and then along the Princess Promenade. We stopped at the Roots Fountain and had our picture taken. Then up through the San Juan Gate to EL Morro. Old San Juan is full of beautiful statues and buildings. You’ll pass many of them, such as the Roagtiva and La Forteleza, where Jose explains the who, what where, when & why of what you’re looking at. We also made a quick stop at Casa Blanca, to see the gardens. And we went by the cemetery and a number of public squares.

The two-hour tour also includes entrance to El Morro fort and about 30 minutes of a guided walking tour inside (you leave the Segways parked outside the fort). We have been in the fort loads of times, but when you go with a guide, it really adds another dimension to the place. Jose has lots of little known facts, and he points out many easily overlooked things. At many of the stops, Jose will take your picture if you want, so you will have photos to show all your friends. I have to say that riding a Segway is one of those experiences that seems to be universally known, but few have ever tried it. During our tour almost every person we passed commented on the Segway and many people took pictures of us on them. It was an interesting and fun experience and after two hours of sightseeing in hilly and beautiful Old San Juan we hadn’t even worked up a sweat! Now that is the way to enjoy the old city!

The Short Tour

The 1 hr tour follows the first part of the route of the two-hour tour. You will see and learn about the old jail, the city wall, the Old San Juan city gate, and many of the lovely statuary along the way. This would be a nice way to try the Segways and learn a little bit about the old city at the same time. They also run this tour after dark, so if you’re on a cruise that arrives in port in the late afternoon, you might check these guys out.

The Details

There is a maximum age limit for the tour of 65 years old. The other big issue for this tour is a weight limit. Since you tell the Segway which way to go by shifting your weight, you need to weigh at least 100 pounds so the machine can feel it. Jose did say, for children who weigh less than 100 pounds, they may be able to make a short tour with an attendant walking along side of them to help control the machine. The maximum weight allowed is 260 pounds. You need to be able to stand up for the duration of the tour. And you should wear flat shoes. If you have a knapsack or something like that, you can leave it behind in the office for safe-keeping while you’re on the tour.

The two-hour tour is $93 plus IVU (sales tax), per person. The 1 hr tour is $63.00 plus IVU (sales tax), per person.

If you're happy, let them know it — Don't forget to tip your your bartender, tour guide or trip operator if you enjoyed yourself. Gratuities are appreciated and typically aren't included in the price they charge you.

I hear they now have contracts with some cruise lines, so days ships are in port, it may be harder to get a reservation. Also if you are on a cruise ship, you may not be able to book directly.

They run tours 7 days/week. The two-hour tours are scheduled for 10:30am, 1 pm, and maybe a 4:00pm. The 45-minute tours are done through out the day 8:30 am onwards, as long as there are Segways available. They are pretty flexible with the times, and they can do tours later in the evening if requested.

Reservations are required for the two-hour tours. They can take a maximum of 5 riders on each tour with the guide. If you have a larger group, you will have to be split up an put on back-to-back tours. They have 12 Segways now, so they can run tours every hour if demand requires. You can reserve online or call. If don’t have a reservation, they’re located right at the waterfront, so just pop in and see if they can accommodate your group. They can hold your luggage in their office during the tour.

Allow enough time for the tour itself (45 minutes or 2 hours) and then about another 15-30 minutes (depending on the size of your group) for your training. They ask that you show up at least 15 minutes for your scheduled tour.

You can call them at 787.598.9455 for more information or to make a reservation.

You can get more information or make reservations online on their website www.SegwayToursPR.com

Segway Tours of Puerto Rico is located in Old San Juan on Pier 2, just to the left of the Ferry Terminal (when facing the water). There’s an ice cream shop on the corner by their place. You’ll see the signs.

Click on a placename below to view the location on Google Maps ...

• Segway Tours of Puerto Rico

PuertoRicoDayTrips.com assumes no responsibility regarding your safety when participating in the activities described in this article. Please use common sense! If your mother or that little voice in your head tells you that you are about to do something stupid … then don't do it! Read more about Safety →

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