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A Self-Guided Walking Tour of Old San Juan with Map

October 13, 2019 By Somto Ugwueze 8 Comments

Last updated on April 1, 2023

The streets of Old San Juan were practically built to be strolled for hours. With colorful, Spanish colonial architecture, picture-perfect corners, and mesmerizing views of the Caribbean Sea, you’re bound to have at least a few awe-inspiring moments during your tour of this historic city. Founded in 1521 by Spanish conquistadors, this port city has long been the cultural and commercial hub of Puerto Rico. It is home to some of the country’s most important landmarks, from fortresses to art galleries. Old San Juan is a charming neighborhood at the heart of the city with cobblestone streets, brightly-colored buildings, a plethora of bars and restaurants, and a whole lot of soul. This post will show you how to put together your own walking tour of Old San Juan and experience the must-see sites in the city. It includes a map so that you can follow along on your phone.

Disclosure: This post contains affiliate links, as explained in my disclosure policy

Time required for a tour of Old San Juan

Old San Juan is a compact area so this tour would take you about 60 minutes if you simply walked to each location without stopping. I would budget about 3-4 hours to give you enough time to take in the sites, tour the historic buildings, and enjoy the food. 

Items to bring with you

• Comfortable shoes – some parts of the tour are hilly so it’s a great idea to wear running shoes or something that won’t kill your feet after three hours of walking and climbing fortresses. This is completely up to you. I wore sandals and was mostly fine, except when it came to climbing steep concrete. Next time, I’ll wear definitely wear tennis shoes. 
• Water – stay hydrated, my friends!
• Snacks – pack some fruit, a granola bar, or my go-to travel snack, the WanderBar , a protein bar made specifically for travelers and frequent flyers. I can’t get enough of the Cocoa Crunch flavor.
• Map or GPS – Google maps, Apple maps, or whatever works best for you. Puerto Rico is a US territory so your phone service from any major US carrier should work just fine.
• Camera – you can use your phone camera, but a DSLR will capture those picturesque streets so much better! I always recommend the Nikon D3400 for beginners.

Old San Juan Walking Tour with Map for First-Time Visitors

The best sites to see, food to eat, and things to do in Old San Juan

Castillo San Cristobal

We’ll start at Castillo San Cristobal, the largest fortress that the Spanish built in the New World. A UNESCO World Heritage Site, this fortress is part of the San Juan National Historic Site , an area that includes fortresses, bastions, and the old city wall. Castillo San Cristobal was built in 1783 to protect the city from attacks when other European powers were trying to take over. 

You need a ticket to tour the inside of the fortress, but there’s an outside area with bastions overlooking the Caribbean Sea that anyone can visit. The ticket is $7 and is valid for two days to allow you to see other parts of the San Juan National Historic Site. 

There are three levels to this fortress: the lowest level, the main firing battery, and the observation deck at the top. To get into the fortress, you have to go through some dingy tunnels at the lowest level. Along the way, there are dimly lit rooms, including a dungeon where prisoners were kept for execution. It was creepy, to say the least. 

Once you get past the tunnels, then everything brightens up – literally. You arrive at the main firing battery with rooms on the periphery that overlook the city. There are plaques explaining what the rooms were used for. Lastly, there’s the top level of the fortress, with breathtaking views overlooking the city. I spent a lot of time here just taking in the scenery.

You can purchase your ticket at the San Juan National Historic Site office or call +1 787 729-6777 . The fortress is open every day of the week from 9 am to 6 pm.

Address : 501 Norzagaray Street San Juan, PR 00901 Hours : 9 am to 6 pm every day Price : $7

Calle de La Fortaleza

Calle Fortaleza is a shopping street in Old San Juan, located by the governor’s mansion. There are tons of little shops and restaurants here. This street used to be an Instagram hotspot when there were umbrellas floating at the top. When I visited San Juan in Old San Juan in July 2019, the umbrellas were unfortunately no longer there. The street was barricaded during my visit to San Juan because of protests against the government due to an political scandal. Not going to complain. People’s livelihoods are more important than my Instagram photos. That said, the umbrellas could be back again, as they are a major tourist attraction. I’ll have to confirm when I visit again.

Address : Calle de la Fortaleza San Juan, 00901, Puerto Rico Hours : 24 hours, 7 days a week Price : Free

La Fortaleza

La Fortaleza, also known as Palacio de Santa Catalina, is the official residence of the governor of Puerto Rico. Located at the base of Calle de La Fortaleza, it is the oldest, continuously used governor’s mansion in the western hemisphere. This blue building sits on a fortification by the Caribbean Sea that was built by the Spanish in the 16th century to protect the city against foreign attacks. You can take a free 30-minute tour of the interior, courtyards, and gardens every weekday from 9 am to 4 pm. To book a tour of La Fortaleza before you arrive in San Juan, you can email [email protected] or call +1 (787) 721-7000. Just can also arrive in person at the tourist office next to the mansion and book your tour, although same-day availability is not guaranteed. I didn’t know you could tour this building when I visited so I’m bummed! Now you know. 

Address : 54 Calle Fortaleza Edificio de la Real Audiencia San Juan, PR, 00901 Requirements : Must be at least 21 years and have a valid photo ID Hours : 9 am to 4 pm Price : Free

El Batey Bar

I was looking for some cheap mojitos and found this place on Yelp. When I walked in, I felt like I had stepped into some kind of punk rock tattoo parlor. That’s the vibe of this place – dimly-lit and dingy. With the somewhat pretentious writings on the wall, like ‘Prohibido Joder,’ and “Donald Eres Un Pendejo,” (not that I disagree with this statement), I didn’t have a good feeling about the place at first. 

But it turns out the mojitos were good and cheap. Also, the bartender, Javier, engaged me in a conversation for like an hour. Then, I ended up chatting with some locals at the bar, too. So I ended up liking this bar after all. It’s a great place to unwind and maybe meet new people.  El Batey is known for its casual atmosphere, politically incorrect posters, and affordable drinks.

Address : 101 Calle del Cristo, San Juan, 00901, Puerto Rico Requirements : Must be at least 21 years and have a valid photo ID Hours : 3 pm to 12 am every day Price : $3-$10

San Se Marisquería Bar de Tapas

San Se Marisqueria is a tapas bar-restaurant located down the street from the co-living community, Outsite San Juan, on Calle San Sebastian, from which it gets its name. This is by far the best restaurant in Old San Juan where I had the privilege of dining. I would recommend their Mofongo , a signature Puerto Rican dish consisting of mashed plantains, and their impeccably-seasoned Pulpo , or octopus (shown above). They are both unbelievably delicious! I’m sure the other items on the menu are equally so.

There is also a bar area serving cheap piňa coladas, mojitos, and other cocktails, which are around the same prices as other San Juan establishments. The food, though, is more expensive than at your average Old San Juan restaurant, but I think this place is definitely worth a visit. You can order takeout, but there’s no delivery.

Address : 152 Calle de San Sebastián, San Juan, 00901, Puerto Rico Hours : 3 pm to 2 am every day except Tuesday, when it’s closed Price : $3-$10

Calle Imperial

Calle Imperial is one of the iconic streets in Old San Juan with a flag of Puerto Rico on the wall. This flag is no ordinary mural; it has cultural significance. Known as Callejon de la Puerta Bandera, it is a symbol of Puerto Rican identity and pride and one of two flag murals in Old San Juan. The other one, located on Calle San Jose, is black and white. Calle Imperial is one of the most iconic places to snap a photo in San Juan. I wanted to get a photo of myself here and waited for someone to walk by. No one did so I just took a photo of the wall. The struggles of solo travel. Next time, I’ll be sure to take a tripod!

Address : Calle Imperial San Juan, 00901, Puerto Rico Hours : 24 hours, 7 days a week Price : Free

Castillo Felipe del Morro

Further west of Castillo San Cristobal is another fort called Castillo Felipe del Morro, simply known as El Morro. This fortress is also part of the San Juan National Historic Center. It has six levels which were built over the course of 200 years, starting in the 1500s.  This place has so much history, it will take you at least 90 minutes to fully tour and appreciate all the parts, from the dungeons in the lower level to the narrow stairwell that leads to the top level to the canons on the roof.

El Morro was one of the original fortifications built by the Spanish to protect San Juan from foreign invaders. Today, it’s popular among locals and tourists alike. The different levels, particularly the higher ones, offer incredible views of the Caribbean Sea and the entire city of San Juan. All around the structure, you’ll find many garitas , or guard posts, which are a great place to snap a photo. 

The best way to experience El Morro is to do a guided tour, like this guided tour of El Morro with an entry ticket that includes stops at other must-see places in Old San Juan. This tour is organized by Get Your Guide, a tour operator I’ve been using since 2016. I love how deeply informative and engaging their tours are, from Spain to China. I always leave their tours with tons of notes on my phone. The local tour guides they employ are knowledgeable and friendly.

Address : 501 Calle Norzagaray, San Juan, 00901, Puerto Rico Hours : 9 am – 5 pm every day Price : $10

Paseo de la Princesa

Paseo de la Princesa, which translates to Princess Promenade, is a pedestrian walkway by the San Juan Bay. Located in the historic district of Old San Juan, this picturesque promenade was built in 1853. It has undergone various renovations since then. You’ll take in breathtaking views of the San Juan Bay on one side, with the waves from the Caribbean Sea crashing against the shores. On the other side, you’ll get a good look at the majestic fortifications that were built centuries ago to protect the city from invasion.

Beyond the views, you’ll find a long line of street vendors selling everything from empanadas to handmade crafts to beaded jewelry. There is also an famous work of art, the Raíces Fountain, that features paintings of the different ethnic groups that make up Puerto Rican society – the African-descended people, the indigenous Taino people, and the Spanish conquistadors. This promenade is the perfect place to go for a stroll in the afternoon, people watch, and go souvenir shopping.

Address : Paseo de la Princesa, San Juan, 00901, Puerto Rico Hours : 24 hours, 7 days a week Price : Free

Catedral de San Bautista

Catedral of San Juan Bautista, also known as the Cathedral of Saint John the Baptist, is the second-oldest cathedral in the Americas. Completed in 1540, this Roman Catholic cathedral finest examples of Spanish colonial architecture. It features a mixture of Gothic and Baroque architecture, with an ornately-decorated altar made of gold. This towering cathedral has played a pivotal role in the cultural and spiritual life of Puerto Ricans for centuries, with many weddings, baptisms, and even state occasions taking place here. The Spanish explorer Juan Ponce de León is also buried at this cathedral. There are many churches in San Juan but Catedral de San Bautista is perhaps the most important. That makes it a must-see on your visit to Old San Juan, even if you’re not Catholic. The church is open to the public for free.

Address : 151 Calle del Cristo, San Juan, 00902, Puerto Rico Hours : 9 am – 4 pm every day Price : Free

Plaza de Armas

Plaza de Armas is the main plaza, or public square, in Old San Juan. Originally built as a training facility for the Spanish military, the plaza is now a a place of leisure. Tourists and locals alike gather here to enjoy concerts, festivals, and other cultural events. There are also a few notable structures at this plaza, including a a statue of the Spanish explorer, Juan Ponce de León and a statue of King Juan Carlos I of Spain. At the center, you’ll find a fountain with statues of religious and historical figures. This plaza is a great place to end your tour of San Juan. In the vicinity, you’ll find the San Juan City Hall and the Department of State building of Puerto Rico. You can sit down, relax, and bird watch before returning to your accomodation.

Address : FV8M+48H, San Juan, 00969, Puerto Rico Hours : 24 hours, 7 days a week Price : Free

Want to tour Old San Juan with a local guide?

While I’m a huge fan of self-guided walking tours, I also know the value of having a local guide show you around their city and explain what you are looking at. That’s why I’d recommend doing at least one guided tour of San Juan with a local operator in addition to your own self-guided tour.

One of the perks of doing a guided tour with my favorite tour operator, Get Your Guide, is being able to skip the long lines. If you wait until you arrive in San Juan to buy your tickets, you may be waiting for a long time, especially during the peak summer travel season. With a guided tour, you also get to learn directly from a local about the culture and history of San Juan, allowing you to better appreciate the sites, food, and other attractions. Below are the Get Your Guide tours I’d recommend in Old San Juan.

First, we have a foodie walking tour of Old San Juan that will give you a taste of Puerto Rican cuisine. A local guide will take you to the must-try restaurants in Old San Juan, where you’ll sample 10 delicious bites. You’ll also participate in a culinary class, where you’ll learn how to make the classic mofongo . The 3-hour tour comes with a bonus rum cocktail so that you can try Puerto Rico’s specialty drink.

The second tour I’d recommend is a sunset walking tour of Old San Juan . The sunsets in San Juan are something special, and you’ll get epic photos of the city at this time of the day. During this tour, a local guide will take you to historic places that aren’t included in this self-guided walking tour, such as the iconic Plaza Colón, Plaza de la Barandilla, and the ancient Palacio de la Intendencia. You’ll also discover the urban legend and mystery behind a chapel known as Capilla del Santo Cristo de la Salud. This 2-hour tour will fully immerse you in Puerto Rican culture and history.

Last but not least, it’s a good idea to get off the island and take in the whole scenery from a sailboat! This 90-minute sailing tour of San Juan is one of the best ways to experience the city. You’ll board a topsail and cruise around Old San Juan, taking in the city from a different vantage point. The sailing adventure comes with complimentary drinks, including rum, of course, so that you can unwind while you spot El Morro, La Fortaleza, and other iconic structures in the city. This would be an epic way to conclude your visit to San Juan.

Travel Resources I Love

CabinZero 36L Backpack – this trusty backpack has has been my go-to luggage for both domestic and international trips since 2018. I’ve used dozens of backpacks over the years and keep coming back to this one. I almost never check in luggage so I need a carry-on bag that is spacious, sturdy, and comfortable, with a laptop compartment. The Cabin Zero 36 L fits the bill. The size makes it small enough for a weekend getaway and big enough for a month of backpacking in Europe. The bag also comes with a tracker in case it gets lost. How convenient! Check out my complete review of the backpack.

Travel WiFI Pocket WIFI Device  – With portable WiFi, you can say goodbye to ridiculous roaming charges and SIM cards for good. I’ve been using the Travel WiFi Portable Hostspot device for years and love the peace of mind it gives me. The device provides 3G-4G WiFi for at least 6 hours and works in 100+ countries. In my experience, it lasts 9 hours. It also works in a variety of landscapes and terrains. I even filmed a Facebook Live from a boat in the Atlantic Ocean using my device. I can also use Google Maps, request an Uber, call my mom, and do tons of other things I couldn’t do before. Quick tip: turn off the device when you’re not using it so that the battery can last longer.

Booking.com – Booking.com is my go-to website for booking discounted accommodations around the world.  What I love most about Booking.com is the variety of properties you can find, from luxury apartments to treehouses to university housing. It’s hard to beat the insanely low prices. The website also has a flexible cancellation policy, which is great if things come up or you change your mind. 

For more travel product recommendations, check out my travel essentials page .

One more thing: if you enjoyed this post, please share it!

Somto Ugwueze

Hi! I'm Somto. Two years ago, I stopped making excuses, ditched my indecisive friends, and started booking flights. Today, I'm a full-time solo traveler on a mission to inspire young women to seek new adventures.

@somtoseeks

Reader Interactions

January 10, 2020 at 12:43 pm

I just got back from Puerto Rico shortly before Christmas 2019. Visited beautiful Old San Juan, with it’s lovely blue cobblestone streets. You forgot to mention their love of gatos! The cats roam the area and are fed by those that live there. ❤️

July 19, 2020 at 9:51 pm

Hi Peggy, yes, I forgot to mention those gatos! I loved seeing all the cute cats roaming around.

February 3, 2020 at 4:15 pm

Isn’t there a walk outside the walls of the city?

March 9, 2021 at 1:18 am

This is AMAZING!!!! It’s absolutely perfect, exactly what I’ve been looking for! THANK YOU!!! I never ever ever write comments/reviews on websites, but I absolutely had to for this. I’m with a group of 11 friends who wanted to see Old San Juan but didn’t plan anything specific, and I didn’t want to waste the whole day going back and forth. Having this all set up in order is going to save our lives! Thank you!!!

April 23, 2021 at 5:04 pm

Hi Auria, I’m overwhelmed that you found this guide helpful. Keep visiting to find more useful content dedicated to travelers!

June 2, 2021 at 11:42 am

Thanks for creating this blog! It was just what I needed. I was asked to come to Puerto Rico at the last minute for work and decided to bring my 15,16, and 20-year old children. We knew we wanted to visit Old San Juan but didn’t know what to do. Your blog came in handy! We didn’t hit every spot but definitely enjoyed our time. As an update for anyone reading the comments, the tour tickets are now $10 for anyone over 15. 15 and younger are free! Also, there was a food truck near El Morro selling non-alcoholic piña coladas. My children said they were delicious! Keep inspiring us through your travels. You are appreciated!

May 1, 2022 at 8:33 am

Very informative article . Thank you for the order. Will be visiting these places ❤️

March 1, 2023 at 11:04 pm

Thank you for writing this blog!! Very helpful! I am planning a trip with my family. I can’t wait to visit Old San Juan and Puerto Rico! It’s our first time.

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Who Is Somto Seeks?

Hi there, I’m Somtochukwu. Can you try pronouncing that? I've always gone by Somto (Sohm-toe). I'm a child of Nigerian immigrants who decided to pursue her dream of living an extraordinary life. In 2015, I chose faith over fear, packing my bags and moving to Spain with $1,000 in my pocket. This was after being diagnosed with an autoimmune disease that caused me to develop a giant bald patch in the middle of my scalp. Living in Spain and traveling around Europe for a year changed my life forever, allowing me to discover the freedom of solo travel and the freedom of working from anywhere. Today, I’m a full-time travel writer whose mission is to help you navigate this big, beautiful world with confidence and have those omg-pinch-me-moments you’ll remember for a lifetime.

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11 Best Tours & Excursions In Old San Juan, Puerto Rico (2024)

• Old San Juan
• Tours & Excursions

Old San Juan is the old part of San Juan that was built by the Spanish in the 16th Century.

There are lots of tours & excursions to experience here. 

I have lived in Puerto Rico my entire life, and have visited Old San Juan countless times.

In this article, I will cover the 11 best tours & excursions in Old San Juan:

1. Walking tour

This tour is full of history. 

Enjoy the streets of Old San Juan and learn the history of the Spanish Colonial era in a small group setting guided by a local.

Walk through the cobblestone streets and enjoy the essence of Puerto Rico’s culture and heritage. 

Perfect for the whole family!

Below is a video showing a Free Walking Tour in Old San Juan:

You can book this tour with Old San Juan Free Walking Tour .

Learn more about Old San Juan’s most famous attraction in our article Castillo San Felipe Del Morro – All You Need To Know.

2. Personalized tour

A personalized tour that will lead you through the mystical colonial city.

This tour can take you to explore La Perla — the oldest barrio of Old San Juan and the setting of many movies and music videos.

You can book this tour with Atabey Tours .

For more ideas about things to do in the area, read our article the 40 Best Things To Do In San Juan .

3. Food tour

Enjoy the old city while trying the local cuisine.

        View this post on Instagram                       A post shared by Flavors Food Tours (@flavorsfoodtours)

Photo Credit: @flavorsfoodtours

You’ll enjoy various restaurants and tasting spots while learning about the history of the old city.

Check out Flavors of Old San Juan Food Tour in the following video:

You can book this tour with San Juan Food Tours .

Read more about the best food tours in our article 3 Best Local Food Tours In Puerto Rico .

4. Rum and cocktail tour

On this tour, you’ll understand why they call Puerto Rico the Rum Capital of the World.

          View this post on Instagram                       A post shared by Flavors Food Tours (@flavorsfoodtours)

A guided tour where you’ll taste all kinds of cocktails and refreshing drinks while admiring the streets of Old San Juan.

Check out the Craft Cocktails in Old San Juan in the following video:

5. Segway PT and Segway Kickscooter tour 

Enjoy the beauty of Old San Juan from a unique perspective.

Experience a tour of the streets and the fortresses of Old San Juan on a Segway PT or Kickscooter.

Most Segway tours last around two hours.

You can book this tour with Segway Tours of Puerto Rico .

6. Photoshoot tour 

Take this tour with a professional photographer.

You can visit Fortaleza Street, San Cristobal Castle, El Morro Fort, and many other enriching sites while stopping to take photos.

Get in touch with local photographer Carmen Salas to book this tour.

7. Private driving tour 

Enjoy a tour in a private luxury vehicle with a knowledgeable local guide.

You will explore stunning landmarks like the San Juan Bautista Cathedral and the narrowest houses in the Western hemisphere while learning the history behind them.

Below is a video showing a private driving tour:

You can book this tour with Bespoke Lifestyle Management .

8. El Morro tour

Enjoy this extensive tour of El Castillo San Felipe del Morro.

In this tour, you will discover the history of this iconic fortification guided by an expert local guide.

You will visit the famous Castillo San Felipe and take pictures in one of the “garitas,” or guard stations, while learning all about this 500-plus-year-old fort. 

Check out El Morro in the following video:

You can book this tour with Spoon .

9. Murder and mystery tours 

This Mystery Tour is no ordinary excursion.

This self-guided tour is filled with challenging clues that will lead you around Old San Juan. 

Form a team to solve the mystery while experiencing the astonishing landmarks of the city.

Below is a video showing the Clue Murder Mystery Tour:

You can book this tour with Mariott Bonvoys Tours & Activities .

10. Old San Juan & Loiza African town excursion

First, you will visit Old San Juan historical sites and landmarks guided by an expert guide.

Enjoy El Morro and La Puerta de San Juan, then you’ll be taken to the small city of Loíza where you will learn all about the influence of our African and Taino heritage.

You can book this tour with Puerto Rico as a Local .

11. Sailing tour

On this tour, you will enjoy Old San Juan’s architecture from the water.

Sail through Old San Juan’s bay.

Experience its amazing landmarks and history while enjoying refreshing drinks.

Here is a video showing the tour aboard the Amazing Grace:

You can book this tour with East Island Excursions .

FAQ section

What is the best tour for families in old san juan .

The best family tour for families is the Old San Juan Free Walking Tour. There is no age limit for this tour and the individualism of it makes it perfect for the whole family!

What is the best excursion in Old San Juan for cruise ship passengers?

The Old San Juan Free Walking Tour only lasts two hours, which makes it comfortable for cruise passengers who may have limited time before returning to the ship.

Final thoughts

Old San Juan is the historical center of Puerto Rico. 

In my opinion, the walking tour and touring El Morro should be on your list.

If you are looking for other fun tours & excursions in Puerto Rico, then check out our article where we cover the 25 best tours in Puerto Rico .

Old San Juan is only a couple hours from some of Puerto Rico’s famous bioluminescent bays. Learn more by reading our article about Puerto Rico’s bio bays . 

Dimary Hernández Soto

Writer at PuertoRico.com. I have lived in Puerto Rico my entire life. When I’m not writing, I work in the healthcare industry as a Quality Control Specialist. After Hurricane Maria, my teammates and I were responsible for ensuring that life support equipment reached patients in need around the island.

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Old San Juan Walking Tour (Everything you need to know)

Table of Contents

If there’s one part of San Juan that everyone should see, that’s definitely the Old Town. The Old San Juan Walking Tour is the easiest way to learn about the history, culture, and top things to do in Old San Juan.

San Juan is one of the cities that truly stands out with its history and uniqueness. It’s a very walkable area if you want to roam around on your own… but I’ve always preferred a guided tour. So, here is everything you need to know about the Old San Juan Walking Tour .

Can you explore Old San Juan on your own?

100%! I did this many times… it’s an easy place to roam around with all the picture perfect streets, cool shops, and popular bars and restaurants.

How long does it take to walk around Old San Juan?

This walking tour takes around 2 hours… if you wanted to explore on your own, I would give yourself 3-4 hours.

You will definitely want to stop to take photos, check out the local shops, and grab a refreshing beverage.

Is it safe to walk around Old San Juan Puerto Rico?

I have been to Old San Juan many times and never had any issues in regards to safety… but, just like in your own city, use common sense. Don’t wander off into unfamiliar areas late at night or after a bunch of drinks.

What is the most beautiful street in Old San Juan?

Most people would agree on Calle Fortaleza (Fortaleza Street). When you see those billboard worthy photos of people in Old San Juan, there’s a good chance it was taken on Calle Fortaleza.

Some people refer to it as “umbrella street”.

What is the best way to tour San Juan?

I would say walking or biking… at least for me, the weather is one of the main reasons I love San Juan. I try to spend as much time outside as possible.

It is a big area with lots of different neighborhoods, but once you get to an area… it’s walkable.

For example, if you’re staying in Condado, it’s about an hour walk to get to Old San Juan. I walked this many times… but if you’re on a time crunch, I would Uber there (or to wherever you’re going), then walk around and explore.

If you don’t want to have to think about it, check out the top rated walking tour below.

Old San Juan Walking Tour Overview

“Explore the colorful buildings and charming streets of Old San Juan in a small group with the help of writer David Rodriguez, author of ‘The Rise and Fall of the Great Barbate.’ During the course of your day, the knowledgeable author helps you discover the area’s key historic sites and gain new insight into Puerto Rican culture. It’s a great opportunity to learn about the many stories of the people who helped to define this unique neighborhood. Your walking trip’s length is flexible based on your needs, and also includes bottled water.” – Old San Juan Walking Tour

What’s included in the Old San Juan Walking Tour ?

• Local Tour Guide
• Take a walking tour of Old San Juan with author David Rodríguez
• Gain new insight into Puerto Rican culture from a knowledgeable author
• Learn the stories of the people that helped to define this unique neighborhood
• Discover key historic sites like Fort San Cristobal, Plaza de Armas, and the city gates

Why should you embark on the Old San Juan Walking Tour ?

The Old San Juan walking tour has over 1,200 5 star reviews! It will feature certified tour guide that has in depth knowledge of Old San Juan.

Joining the Old San Juan walking tour and being a part of this experience is one of the best things to do while in San Juan.

It’s not only going to teach you about the Old San Juan region, but also you get to see the evolution of the city.

Having that window into the past with the Old San Juan walking tour is well worth the couple hours walking around in the tropical heat.

Plus, the Old San Juan walking tour is very safe, and it takes place in a secure part of the city. So your focus will always be on the experience and on enjoying your time here.

Old San Juan Walking Tour Pricing

Pricing and availability may vary depending on time of year you will be visiting…

You can learn more about pricing, availability, and additional information here .

We highly recommend giving the Old San Juan walking tour a try if you’re passionate about walking tours and exploring the history of the city. There’s a lot to learn here, and you will find yourself immersed into the entire experience and process as a whole. We encourage you to enter this great Old San Juan walking tour and visit places like the city gates, plaza de Armas or the Fort San Cristobal. Check these and many other places today, only with this engaging and fun Old San Juan walking tour! 

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Uber in san juan puerto rico- what you need to know (2024), what is the best atv riding in san juan puerto rico (the ultimate experience), how to explore san juan puerto rico waterfalls, caves, and rivers (5-star rating).

Historical Walking Tours in Old San Juan, Puerto Rico

Immerse yourself in puerto rico culture, history & traditions, old san juan walking tour.

Let’s walk! Explore the historic area of Old San Juan. Step back in time, over 500 years, and learn about the island of Puerto Rico. Visit incredible landmarks while your guide regales you with cultural tales.

• Clock 2 Hours

Why Guests Love Our Old San Juan Walking Tours

Juan was wonderful and so informative! He is knowledgeable about the history of San Juan and PR. He is energetic, witty, and a truly enjoyable person to spend a walk with. He is a gem in San Juan!

Juan Carlos was fantastic. Even after everyone else in my group canceled, he showed up on time to give me a solo tour with a bottle of water (which I was looking for) and a sample of his very own art. His tour was a great start to my adventures in Puerto Rico. He’s a native, perfectly bilingual, and very friendly and accommodating! Highly recommend.

Juan Carlos is great and fun tour guide! I would recommend him to anyone who's looking for a relaxing and comfortable tour!

We had a great time with Juan Carlos on our walking tour. It seemed like we saw the entire island by the time we finished as we circled old San Juan and cut through streets along the way. He even brought us water bottles and some of his own artwork as a souvenir!! We learned all sorts of historical facts and memories we will take home with us.

JC it’s the best tour guide you will find in PR !!! He knows the way around PR. Highly recommend JC whenever you visit Puerto Rico.

• Most Popular!

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

Old San Juan Walking Tour | One Day Puerto Rico Itinerary

Whether you’re visiting San Juan on a cruise or spending a few days in Puerto Rico, an Old San Juan walking tour should be at the top of your list of things to do!

As a former cruise ship worker , San Juan was one of my favorite ports to explore week after week.

One of the best decisions I ever made was taking myself on a self-guided walking tour of Viejo San Juan.

In just 3-4 hours, I was able to hit all of the major historical landmarks and popular photo-ops/ Instagram hotspots– and so can you!

Disclosure: This post contains affiliate links. By making a purchase through one of the links, I may receive a small commission at no extra cost to you. Thank you for your support and for helping me keep this blog up!

How to use this map: Click on the faded star next to the title to save this map, and click the square in the top left of the map before the title to view location details.

Self-Guided Walking Tour Suggested Routes

A self-guided tour through Old San Juan can be broken down into two main sections:

• The coastal perimeter (marked in black on the map)- Where most of the historical landmarks are located
• The interior streets (marked in burgundy on the map)- Where most of the photo spots, restaurants, and shops are found

If you want to hit all the locations listed on this free Old San Juan walking tour, I recommend breaking down your route into the two sections like I did and doing one after the other (in any order).

For those arriving from the cruise ship port, it may make more sense to walk around the exterior first and then end the day perusing the downtown streets.

I began this tour in the interior section as I took an Uber to Plaza Colon. After walking all the way down to the Umbrella Street, I then made my way clockwise to the listed destinations.

The Coastal Perimeter

Paseo de la princesa.

Paseo de la Princesa is a beautiful promenade lined with fountains, lamp posts, and trees— all accompanied with stunning views of the San Juan Bay.

On this picturesque boardwalk, you’ll find street vendors, art exhibits and shops, restaurants, bars, and even live music.

Address: 54 C. de la Fortaleza, San Juan

Where to stay in Old San Juan: Old San Juan Guest House , El Colonial Adults Only , Casa Sol Bed and Breakfast , Fortel Hostel

La Fortaleza

National Historic Landmark La Fortaleza (The Fortress) was built in the mid-1500s for military defense.

Since its establishment, it has served a number of purposes in addition to a fortress, including a prison, arsenal, and its current function as the governor’s residence.

Because the building is still an active government building, those interested in looking inside can only do so through official guided tours. These 30-minute tours are offered throughout the weekdays.

La Fortaleza can be seen from a distance while on the Paseo de La Princesa as well as at the end of the Umbrella Street (Calle Fortaleza).

Address: 63 C. de la Fortaleza, San Juan

Puerta de San Juan

Puerta de San Juan is the city’s iconic colorful gate that’s found at the northern end of Paseo de la Princesa.

It’s a historical landmark that was previously used to protect the city during colonial times. 

Standing 16 feet tall, the gate is also inscribed with the phrase, “ Benedictus Oui Venit In Nomine Domini ,” which means, “Welcome those who come in the name of God.”

Address: Cll Caleta De San Juan, San Juan

Museo de las Americas (Museum of the Americas)

The Museo de las Americas promotes the history and culture of the Americas through permanent and seasonal exhibits.

Visitors can learn about the indigenous, African, and European influences that shaped the Americas into the multi-faceted countries that they are today due to colonization and modern development.

The museum is actually inside what used to be the military’s barracks (Cuartel de Ballajá) during the colonial period. The beautiful courtyard is definitely a sight to take in!

You can also find unique, local folk art during the museum’s Domingo de Artesanos , which is an art showcase on the first Sunday of every month.

Address: Calle Beneficencia, San Juan

Website: museolasamericas.org

Hours: Thursday- Sunday 11 a.m.- 4 p.m.

Price: General Admission- $6; Under 12 and over 65 years old- $4

Need to rent a car while in Puerto Rico? Get a quote from Discover Cars here

Castillo San Felipe del Morro (“El Morro”)

Castillo San Felipe del Morro (also known as “El Morro” for short) is the island’s trademark fortification built at the tip of the San Juan Bay. 

Completed in 1790, the six-level fortress was strapped with a cannon, and together with another yet smaller fort, Fortín San Juan de la Cruz (“El Cañuelo”), the two structures produced a crossfire that would protect the bay’s entrance from intruders.

There’s so much to explore inside the fortress, from barracks and batteries to panoramic views of the bay.

El Morro’s presence domineers over everything in nearby site.

The vast green lawn that leads up to the fort’s entrance is the perfect location for a picnic, sunbathing session, or just a short break during your walking tour.

Although there are always groups of people hanging out, the area is so spread out that you’ll have no problem finding space for yourself away from others.

Tip: Keep your receipt! El Morro and Castillo San Cristóbal only require one entrance fee for both locations, so you’ll be able to get a 2-for-1 deal as long as your receipt shows that you’ve already paid for one ticket.

Address: Calle del Morro & Calle Norzagaray

Hours: Daily 9 a.m.- 6 p.m.

Price: General Admission- $7; Free for children under 15

Cementerio Santa Maria Magdalena de Pazzi

Just outside El Morro you’ll find the Santa María Magdalena de Pazzis Cemetery.

While it may seem strange that a cemetery is a landmark, the beautiful graveyard overlooking the Atlantic Ocean is definitely with a visit.

The cemetery’s location by the water was chosen as a way to symbolize a person’s spirit crossing over to the afterlife.

To this day, many of Puerto Rico’s most prominent citizens are laid to rest here.

If you don’t feel like going down and walking through the cemetery, it can easily be admired from the path leading to/from El Morro. 

Address: Calle Cementerio, San Juan

Cruising to San Juan? Book or plan your cruise with Cruise Critic — the industry’s top site for deck plans, cruise tips, ship details, and more!

Next to Cementario Santa Maria Magdalena de Pazzi and alongside the coast is La Perla, a historical shantytown.

The colorful neighborhood is most widely known recently as the filming location for the 2017 worldwide chart-topper “Despacito” by Puerto Rican artists Luis Fonsi and Daddy Yankee.

La Perla was first established as the location of a slaughterhouse as both slaughterhouses, cemeteries, and homes of former slaves and non-white servants were required to be outside of the main city center in the late 19th century.

Address: Calle Tiburcio Reyes + Calle Lucila Silva + Calle San Miguel + Calle Bajada Matadero

Castillo de San Cristóbal

Castillo de San Cristóbal is El Morro’s sister fortress that was build to protect the city from land attacks.

It’s the largest Spanish-built fortification built in the New World, spanning roughly 27 acres.

The fortress features several sentry boxes ( garitas) which are strategic lookout points that guards would use to keep an eye out for any potential threats.

Visitors can explore the different levels of the fortification as well as get a breathtaking panoramic view of Old San Juan and the bay.

Address: Calle Norzagaray & Route 25R (Avenida Luis Muñoz Rivera)

The Interior Streets

Plaza colón.

Plaza Colón is the land entrance to Old San Juan and can be recognized by its monument dedicated to Christopher Columbus.

The plaza is a good meeting or drop-off point if you’re taking a taxi or Uber to/from Viejo San Juan.

Address: C. de la Fortaleza & C. de O’Donnell

Insure your trip to San Juan with travel insurance. Get a quote with Insubuy here .

Plaza de Armas

Plaza de Armas is one of the city’s main plazas.

On the northern end lies San Juan City Hall, and on the west is the Department of State building.

At this plaza, you’ll find several statues, a fountain, benches, and street vendors selling local pastries and coffee.

Address: C. de San Francisco & Calle San José

Umbrella Street (Calle de la Fortaleza)

Perhaps one of the most Instagrammable locations in Old San Juan, Puerto Rico, Fortzaleza Street is home to the iconic and colorful hanging umbrellas.

The popular attraction is located at the end of Calle de la Fortaleza, just in front of La Fortaleza, where the governor resides.

It’s worth noting that the hanging decor changes periodically, so you might not always see vibrant umbrellas.

During one of my visits, the umbrellas were all camouflage patterned to represent the military.

In 2021, the umbrellas were replaced by a large banner with the Puerto Rican flag’s design.

Address: C. de Fortaleza, San Juan

Hotel El Convento

Hotel El Convento is a chic 4-star hotel with a rooftop pool that’s conveniently located in the middle of the city.

But more importantly, the few blocks around the area are absolutely gorgeous and worth checking out if you want some colorful pictures!

Address: 100 C. del Cristo, San Juan

Catedral Basilica Menor de San Juan Bautista

One block away from Hotel El Convento is the America’s second oldest cathedral, Catedral Basílica Metropolitana de San Juan Bautista, also known in English as the Metropolitan Cathedral Basilica of Saint John the Baptist.

Built in the mid 1500s, the cathedral is where the body of Ponce de Leon is entombed.

Address: 151 C. del Cristo, San Juan

La Puerta de la Bandera- Puerto Rican Flag Door

Any visitor will quickly see that Old San Juan is an oasis of art, from brightly painted buildings to beautiful murals on doors.

Another iconic photo spot in Puerto Rico is the Flag Door, or La Puerta de la Bandera from local artist Rosenda Álvarez.

Located at 51 Calle San José, a mural of the Puerto Rican flag is painted on the door of an abandoned historical building.

Address: 51 Calle San José, San Juan

Callejon de la Puerta Bandera- Flag Door Alley

Yet another popular Instagram photo location is also of the Puerto Rican flag on a door, but this time in an alley at the end of Calle Imperial.

I stumbled upon this mural without prior research as I was so immersed in the beautiful rainbow buildings in the neighboring streets.

If you have time (and enough energy), I definitely recommend spending a good half hour wandering through the area.

The streets are so colorful and perfect for photo ops.

You could even hire a Puerto Rico photographer for a fun and memorable photoshoot!

Address: Calle Imperial, San Juan

Where to Eat

A favorite restaurant among us cruise ship crew members is the Stuffed Avocado Shop .

While it’s not traditional or local eats by any means, it is the perfect option if you’re looking for a healthy meal with lots of fresh ingredients and greens– especially if you’re visiting San Juan on a cruise!

At this build-your-own-bowl eatery, patrons can choose from a wide and delicious selection of bases, protein, sauces, and toppings.

The menu also has a few “Signature Avocados,” with combinations already made for those unsure of what ingredients to put together.

From cauliflower rice and baby greens to pulled pork and mango tuna, the Stuffed Avocado is both tasty and healthy.

Address: 209 C. de San Francisco, San Juan

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Michelle is a freelance writer who has traveled to all seven continents and 60+ countries through various forms of employment. Over the last ten years, she’s worked as an ESL teacher in Japan, a youth counselor aboard cruise ships, and a hospitality manager in Antarctica.

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OLD SAN JUAN FREE WALKING TOUR

WELCOME TO PUERTO RICO!

Travel. Learn. Discover.

  WHAT TO EXPECT:

Enjoy a nice walking tour through Old San Juan, the second oldest city in America and the oldest in the U.S.A. For centuries, the city of Old San Juan was an important military base surrounded by fortifications and walls. This tour invites you to see San Juan through a local’s perspective, learn the history of the forts, walk through the colonial houses, and enjoy the eternal summer of the island and feel the essence and the truth of Puerto Rico. 

- The tour lasts approx. 2 hours -

Free Walking Tour: Old San Juan

*Maximum 5 per booking*

Offered Daily

Duration Varies

Free Walking Tour: Art District

*Santurce through Cerra St.*

1 hr 30 min

Private Tour

Through the Old San Juan

Start in $200

Pick-Your-Trip Tour

Through the Island (Max 3 ppl.)

start in $300

CONTACT US:

- For group tours & questions -

+1787-505-5581

Thanks for submitting!

MEETING POINT:

*The tour starts everyday at 10AM*

Two Sisters Abroad

two sisters exploring the world

The 16 Best Things To Do in Old San Juan, Puerto Rico

Old San Juan, Puerto Rico is a charming neighborhood that’s packed full of history and sites to see. Founded over 500 years ago, many people are surprised to learn that Old San Juan is the oldest city in the United States. Today, the city retains its historical charm and is famously known for its colonial Spanish architecture, brightly painted buildings and cobblestone streets. Although Old San Juan is small, you can easily spend a couple full days exploring this beautiful area. Ready to plan your trip to Puerto Rico? Keep reading for the 16 best things to do in Old San Juan! 

FAQ: The Best Things to do in Old San Juan

• At least one day, but I recommend two. Check out my post all about how to have the best 48 hours in Old San Juan . 
• Old San Juan is a neighborhood in the city of San Juan. It’s located on a small island that’s connected to the rest of San Juan by bridges. 
• Yes! Playa del Capitolio is about 15 minutes from Old San Juan and Balneario El Escambrón (Escambron Beach) is around 30. 
• No, Old San Juan is small and very walkable. If you’re staying in Old San Juan, definitely walk everywhere and Uber to other parts of the city. 
• Yes, it’s very safe and also very pretty at night. You’ll also find great nightlife – especially near La Factoria bar. 
• The drinking age in Puerto Rico is 18. 

The 16 Best Things to do in Old San Juan

1: wander the colorful streets.

The first thing I recommend doing when arriving in Old San Juan is taking some time to wander around the streets. 

Old San Juan is small and extremely walkable and this is a great way to get oriented, see colorful architecture and start your day. Every single street is beautiful and it’s truly a photographer’s dream.

If you’d like to take a guided walking tour to learn more about the important sites and history of the city, there are tons of great options.

Walking tours of Old San Juan:

• Old Town Sunset Walking Tour
• Photography & Historical Walking Tour in San Juan

2: Tour El Morro

Visiting El Morro is always a top recommendation for the best things to do in Old San Juan! 

Castillo San Felipe del Morro, shortened to El Morro, is a military fort overlooking San Juan Bay. Construction of this fort began in the 16th century by the Spanish and now this impressive fort is open to the public 7 days a week. 

Tickets are $10 for adults and free for children 15 and under.

TIP: once you’ve paid the entry fee to El Morro, you can also visit Castillo San Cristobal (mentioned below) without having to pay another entry fee. 

Some walking tours of Old San Juan include entrance to El Morro as well as a guided tour.  

Guided Tours of El Morro:

• Inside El Morro Castle & Old San Juan Walking Tour
• El Morro Fort Entry Ticket & Old Town Walking Tour
• Explore El Morro Fort: History and Walking Tour of Old San Juan

El Morro Lawn and Kites 

To get to El Morro, you’ll walk across a beautiful lawn area. This is the windiest point of Old San Juan and you’ll often see people relaxing on the lawn and flying kites. 

Be sure to also walk down the lawn to the Cementerio Santa María Magdalena de Pazzi (The Santa María Magdalena de Pazzis Cemetery). Located on the water, just outside of the walled city, this colonial era cemetery dates back to 1893. 

3: Walk Along Calle Norzagaray for Ocean Views

Calle Norzagaray is one of the central streets in Old San Juan and parts of it also boast beautiful ocean views. You can walk between both major forts in Old San Juan, El Morro and San Cristobal, while enjoying the ocean views and architecture on the way. 

With no stops, the walk between the two forts is 15-20 minutes. 

Starting at San Cristobal, walk along the sidewalk passing by the entrance to La Perla neighborhood and the Museum of San Juan , finally ending up on the lawn of El Morro.

4: Visit Castillo San Cristobal

Castillo San Cristobal is the second most famous fort in Old San Juan, after El Morro. San Cristobal was built to protect  San Juan from Eastern attacks, and therefore, is located on the opposite side of Old San Juan from El Morro. Construction began in 1634 and took 150 years to complete. 

Tickets to San Cristobal are $10 for adults and free for children 15 and under. Your ticket for San Cristobal will also grant you free access to El Morro , and vice versa .

5: Explore La Perla on a Guided Tour

La Perla is one of the most infamous places in Puerto Rico and happens to be nestled right along the Atlantic coast in Old San Juan. 

This neighborhood has had a difficult past and used to be known for being one of the most dangerous areas on the island. La Perla is outside of the walled city of Old San Juan and since its creation has been largely neglected by the government.

However, in the past few years, especially following the production of Luis Fonsi’s famous hit Despacito, who’s music video was filmed in La Perla, the neighborhood is becoming more open to tourists. This being said, it’s still largely residential and nowhere near as touristy as the rest of Old San Juan. There are some streets you should not visit and many locals will warn you not to visit at all. 

Guided Tour of La Perla

If you want to visit La Perla, which I highly recommend, definitely do it on a guided tour. This way, you’ll be visiting the neighborhood safely and respectfully and in a way that supports locals and their businesses. 

I highly recommend taking a tour with Carolina from La Perla Like a Local . You’ll learn the history of the neighborhood, meet locals, support small businesses and really gain an understanding and appreciation for La Perla. You will also feel completely safe. 

After the tour, you’ll also be much better equipped to visit La Perla again on your own. There are great bars in the neighborhood, beautiful street art and everyone we met was so friendly and welcoming. 

You will see some travel blogs and websites saying “it’s totally okay to visit La Perla, no one will stop you and it’s safe!” While this is true in some cases, I still don’t recommend visiting on your own, especially on a first trip. If you do choose to explore on your own:

• Know exactly where you’re going.
• Don’t take photos without asking first (especially of residents or their homes.)
• Understand that there is no police presence in this area and it is still known for drug trafficking. 

I don’t say any of this to scare you, but instead so you understand where you’re visiting and how to do it in a way that is safe for you and respectful to locals who call La Perla home.

6: Have a Piña Colada at Barrachina and El Caribe Hilton

Fun fact: the Piña Colada was invented in Puerto Rico! However, there’s a long standing debate over which establishment, Barrachina or El Caribe Hilton , really made the first one. 

Both spots serve up delicious drinks, but they have slightly different flavors. I recommend trying both to see which you prefer! 

El Caribe Hilton (one of the *supposed* piña colada inventors) is located just 5-10 minutes by car from downtown Old San Juan and is a great place to stay. 

If like a good cocktail, a craft-cocktail walking tour is a fun way to discover great bars and try some delicious drinks.

7: Check out the Art Galleries

Old San Juan is filled with a variety of art galleries and shops. You’ll find handmade souvenirs as well as paintings and ceramics. It’s so fun to pop in and out of these shops and purchase an art piece to bring home. 

A few of my favorite art shops and galleries include: 

• The Poet’s Passage
• Puerto Rican Arts and Crafts
• Galería Éxodo

8: Take an Art Class

In addition to visiting art galleries, taking an art class is so fun and such a great way to learn more about local art and culture. I took a painting class at San Juan Sip & Paint and it was a blast. 

I’m not a very good painter, but with the step by step instructions from the artist, my painting turned out pretty cute. You also get a beverage to sip on (alcoholic or non-alcoholic), making this a fun date night, friends night or even a family activity. 

If you’d rather make something you can wear, you can also take an espadrilles making class . Espadrilles are traditional Spanish shoes that have now spread in popularity across many parts of the world. These shoes are cute and such a fun souvenir to wear home and on other trips!

9: Take a Food Tour and Eat at Delicious Restaurants

Puerto Rican food is delicious and there are so many fantastic restaurants to check out in Old San Juan. A great way to get acquainted with the local dishes when traveling is to take a food tour – it’s always a huge highlight of my trips! Food tours are so much fun and such a great way to try many different menu items. 

They’re also a great way to learn about local restaurants, get recommendations from your guide and decide where you want to go back to for more meals. 

Food Tour Recommendations:

• Old Town Foodie Walking Tour with Tastings
• Old San Juan Walk and Taste Tour

If you don’t want to take a food tour, but instead want to jump right into trying out local restaurants, a few of my favorites for traditional Puerto Rican food are:

• Deaverdura (there will likely be a line)
• Cafe el Punto  
• Cafeteria Mallorca (breakfast and lunch)

10: Eat Mofongo, Tostones, Mallorcas and Paletas

As we’ve been discussing, there is so much great food in Puerto Rico! A few must-try dishes on a first trip to the island definitely include mofongo, tostones, mallorcas, and, my favorite, paletas. 

Plantains are very popular in Puerto Rico and many traditional dishes are plantain-based or have plantains as a side dish. 

Many side dishes, like tostones, are served with the famous mayo-ketchup. This dipping sauce, as you could probably guess by the name, is made by mixing mayo and ketchup. I don’t really like mayo or ketchup on their own, but for some reason I really like mayo-ketchup.

Must-try Puerto Rican foods:

• Some restaurants also serve a vegetarian version. 
• Tostones are crispy, fried smashed plantains.
• Mallorcas are a fluffy, sweet bread (kind of like fried dough) that are sprinkled with powdered sugar. Many people eat mallorcas with ham and cheese, but there are several varieties.
• My favorite popsicle shop is Señor Paleta (it’s also the most famous), but Zippops Gourmet Paletas are also excellent. 

These are just a few delicious foods you’ll find in Puerto Rico! Also be on the lookout for amarillos (fried sweet plantains), alcapurrias (deep fried meat fritters), bacalaítos (fried cod fritters) and empanadillas (fried turnovers with a variety of fillings).

11: Visit the San Juan Cathedral

Built in 1540, the Metropolitan Cathedral Basilica of Saint John the Baptist is the oldest cathedral in the USA and the second oldest in the Americas. It’s also among the oldest buildings in San Juan.

It’s located right next to the historic Hotel el Convento , a former convent dating back to 1651.

12: Drink Puerto Rican Coffee

If you’re a coffee lover, you’ll love Puerto Rico! Puerto Rican coffee is so good and there are so many fantastic coffee shops around Old San Juan. 

A few of my favorites include: 

• Cafe Cuatro Sombras
• Bien Papayas  

Don’t forget to grab a bag of local coffee (or two!) to bring back home!

13: See the Umbrella Street and Governor’s Mansion

This section of Fortaleza Street, starting next to Anita La Mamma Gelato (very good, by the way) and ending at La Fortaleza (the Governor’s Mansion), is known for its colorful hanging umbrellas. 

Depending on the time of year, these umbrellas are swapped out for other equally beautiful decorations, like kites or flags. 

This street is one of the top photo spots in Old San Juan, however, for the past several months (and likely for the foreseeable future) the street is closed. You can still see the umbrellas, but you can no longer walk under them. They’re still pretty to see, but it makes taking photos a little difficult. 

There is a constant police presence in this area as well as barricades blocking the street, so it’s definitely not possible to pass through for photos directly under the umbrellas.

14: Make your own Bracelet at Caribbean Beads

This little hidden gem is such a fun place to go to make your own jewelry! At Caribbean beads you can choose from a huge variety of beads, charms and chains to be expertly assembled into a one of a kind piece of jewelry. 

I went with a group of friends and we all had so much fun picking out charms and making bracelets. The prices are very affordable as well, with all of our bracelets ranging from $14-$20.

This is the perfect activity for rainy weather!

15: Relax on the Beaches

Puerto Rico is known for its amazing beaches. Although Old San Juan isn’t the beachiest place on the island, there’s still a couple decent beaches within walking distance. 

Start on Paseo Puerta Tierra, a walking path with ocean views, and shortly you’ll come to Playa del Capitolio. 

As its name suggests, Playa del Capitolio is right in front of the Capitol Building. This little beach isn’t great for swimming, but it’s a nice place to come to read a book, watch the sunset or look for sea glass. There are no amenities, so you’ll need to bring everything you need.  

If you keep walking for another 20 minutes along Paseo Puerta Tierra, you’ll arrive at Balneario El Escambrón. This beach and park area has bathrooms and vendors and is somewhere you could easily spend an entire afternoon. 

From Balneario El Escambrón, you can walk or Uber back to the old town for a few dollars. If it’s after sunset, I recommend Ubering as the street lamps aren’t the best and the path is less busy at night. 

16: Have a Drink at the Famous La Factoría

A trip to Old San Juan isn’t complete without a night out at the famous La Factoría ! This bar has been named the best bar in the Caribbean and is often featured as one of the 50 Best Bars in the World . 

What makes La Factoría especially unique is that it’s six bars in one, all connected through hidden (and not so hidden) passageways. Each of these bars has its own unique vibe, music and drink menu. It’s so fun to wander through La Factoría checking out the different rooms. 

Tip: if you want to visit all six bars, plan to go after 11pm, as sometimes not all of the rooms are open until then.

If you’re traveling solo or in a small group, a great way to meet new people and enjoy a night out is to go on an Old San Juan Bar Crawl !

For those who’d like to experience more bars outside of Old San Juan, definitely consider a tour to La Placita de Santurce . This is the perfect area for bar-hopping, nightlife, great music and dancing.

You can also easily visit La Placita on your own. There are tons of bars right next to one another and it’s a very fun time. Keep in mind that these bars are not at all fancy and feature an indoor-outdoor vibe.

More Fun Tours

If you have extra time in Old San Juan, there are even more fun and unique tours and activities to partake in. Below are a few great options!

• Old San Juan: Sunset Cruise with Drinks
• Guided Water Bike Tour with El Morro Fort Views
• Old San Juan Murder Mystery Tour
• Old San Juan Segway Tour

The Best Hotels in Old San Juan

Old San Juan has a great selection of hotels, ranging from small, family run establishments to adults-only luxury properties. When visiting Puerto Rico, I love to stay right in Old San Juan, as everything is very walkable and the area is so beautiful. 

Old San Juan isn’t beachfront though, so if you’re looking for a hotel with a beach, I recommend staying in the Condado neighborhood (known for its beaches) and Ubering into the old town. 

Hotels in Old San Juan: 

• Decanter Hotel
• Navona Studios  
• El Colonial  – Adults Only 
• Hotel El Convento
• Villa Herencia Hotel
• Fortel Hostel  

Hotels in the Condado area:

• Caribe Hilton (between Old San Juan and Condado)
• Casa Wilson Inn
• Condado Ocean Club
• Casa Botanica Hotel (close to Condado)
• Trópica Beach Hotel (close to Condado)

Ready to start exploring? I hope you enjoyed this post about the best things to do in Old San Juan, Puerto Rico! If you have any questions, please leave us a comment below or DM us on Instagram, @twosistersabroad .

If you enjoyed this post, we also appreciate you sharing it on social media!

Other posts to check out:

• Itinerary for 48 Hours in Old San Juan
• The Ultimate 7 Day Road Trip Around Puerto Rico

This guide includes affiliate links! Read our disclosure  here .

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Restaurants

• Bars and Night Life

About Old San Juan

• Child Friendly Attractions
• Historic Places
• La Fortaleza
• The Legend of La Rogativa
• A Walk Down Paseo de la Princesa
• Old San Juan Videos
• Old San Juan Gallery
• Insider’s Tour
• Night Legends & Ghosts

Religious Sites Tour

• Capitol & Fort Tour
• La Parguera
• Gilligan’s Island
• Caja de Muerto Island
• A Walk Along Paseo de la Princesa
• Vacation House and Apartment Rental
• Grocery, Health Food Stores, and Pharmacies
• Specialty Stores
• Clothing, Handbags & Shoes
• Factory Outlets
• Art Galleries
• Jewelry Stores
• Events & Festivals
• Major Holidays
• Events in Old San Juan
• Festivals in Old San Juan
• San Sebastián Festival

Map of Old San Juan

• Trolleys and Garitas

Useful Information

• Transportation
• Cruise Ship Travel
• Accessibility

Disclaimer:

Come and explore the second oldest city in the Western Hemisphere. Old San Juan is actually an island connected to the main island by bridges on the eastern side. The oldest section is on the west side and walled in on 3 sides. The historic city is divided into seventeen square blocks. The northern side of the city is uphill and is comprised of the residential area of town. The southern part, or port area (ports 1-4), is the commercial and tourist section that is comprised of shops, piers, and most of the restaurants.

• Walking Tours

Numerous companies offer Old San Juan city tours. They range from theme-specific tours such as culinary or coffee-lovers’ tours to general history tours. Unfortunately, some are too touristy for our liking. With Iggy’s help and expertise, we offer creative walking tour options that emphasize more of a local and cultural flavor still full of history, food, and yes, “café.” Tours: Insider’s Old San Juan Tour – What is it like to live in Old San Juan? Where do locals eat, shop, and enjoy their “cafecito?” Can I go

Top 10 Things to Do

Whether you are only in Old San Juan for a few hours or an entire week, these are the sights that you won’t want to miss while you are here. 1. El Morro As one of the first military defenses in the Americas, it brings you back in time and has an amazing view of the entrance to the San Juan bay. Cruise ships entering or leaving port are almost at the same height as the 6th level of the fort. This remarkable Spanish military fortification took almost 250

Come and explore the second oldest city in the Western

Travel Guide

Old San Juan has a variety of upscale, mid-range, and budget-friendly lodging options to enjoy this old city and its many

Old San Juan is a gastronome’s delight. The options are just about endless.  Whether you are looking to sample the

Out shopping for souvenirs? Looking for authentic hand crafted gifts not the usual plastic items made in China? Look no further

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Insider’s Old San Juan Tour

Capitol & Fort

Night Legends & History

More Great Places to See in Puerto Rico

If you desire to see even more of the island, or you are looking for a little adventure, Puerto Rico has some really spectacular sites all over the island. This list will give you a taste of what you can find.  

Top 10 Things to Do in Old San Juan

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The 10 Best Things to Do in Old San Juan, Puerto Rico

Zen Rial / Getty Images

While Old San Juan has no beaches, no resort hotels, and not a whole lot of natural beauty, it's still one of the most interesting places to visit in Puerto Rico. For all that it lacks, San Juan’s old city (also called Viejo San Juan ) is known for its rich culture and history—established in 1521, it’s the oldest city in the United States to be founded by Spanish colonizers in the New World, as St. Augustine, Florida , was settled a little later in 1565—beautiful architecture liberally splashed with tropical colors, and timeless magic that makes it one of the most enchanting destinations in the Caribbean. You could spend many happy days just walking around the walled city, sampling delicious Puerto Rican cuisine, and dancing to salsa all night alongside the locals. If you're planning a trip, these are the activities worth putting on your itinerary.

Go on a Guided Walking or Foodie Tour

Flavor Food Tours

If you’d prefer to learn more about the places you’re passing by on a stroll through the colorful streets of Old San Juan, consider booking a walking tour with guide Debbie Molina Ramos , who has been leading educational walks around the city since 1999. Choose from daytime or nighttime tours to see the area in a different light.

Those interested in tasting their way around the old city can choose from several foodie-themed tours by Flavors Food Tours and Spoon , which each offer small groups the chance to sample bites from different restaurants around Old San Juan and in some cases, rum-based cocktails, depending on which tour you choose.

Sip Piña Coladas Where They Were Created

Steve Lupton / Getty Images

While you can find piña colada cocktails all over Puerto Rico (it is the national drink, after all) it might be more memorable to indulge in the place they were created. Head to the Caribe Hilton , located on Calle San Gerónimo in Old San Juan, where, in 1954, bartender Ramón “Monchito” Marrero famously blended coconut cream, pineapple juice, and rum to create the world’s first piña colada.

Visit the Old Forts

Walter Bibikow / The Images Bank / Getty Images

History buffs, rejoice! Old San Juan is home to several massive fortresses whose cannons, ramparts, and layered defenses have guarded the walled city for centuries. Start by visiting El Morro (full name: Castillo San Felipe del Morro ) and Castillo de San Cristóbal , which are among the most visited attractions on the island, and for good reason. Then, stop by the governor's mansion, called La Fortaleza (the Fortress) because it served as one of the Spanish settlement's early defensive structures.

Take a Sunset Stroll Along Paseo de la Princesa

Paseo de la Princesa ("Walk of the Princess") is a broad promenade that begins near the docks at the foot of the city and leads to the lovely Fuente Raíces (Raíces Fountain). On weekends, you're likely to find all kinds of stalls lining the road, and occasionally, a free musical or cultural performance to enjoy. Paseo de la Princesa hugs the old perimeter wall of the city and beyond the fountain, continues around Old San Juan to the San Juan Gate, the last remaining of the city’s original five entry points. The best time to enjoy the walk is during sunset when you can take in gorgeous views of the bay from the fountain and escape the midday heat.

Dance the Night Away

Discover Puerto Rico

While salsa dancing and Puerto Rico go hand in hand, the island isn't exactly crawling with hallowed halls of salsa. While old standards like the Nuyorican Café (where Mick Jagger once danced the night away) have closed, newer spots like La Factoría and La Vergüenza Puertorrican Chinchorro —where you can also dance the rumba, bomba , and plena —in Old San Juan have really stepped up to the plate.

Check Out the Former Home of Juan Ponce de León

James Byrum / Flickr / CC BY-ND 2.0

One of the oldest structures in Old San Juan, La Casa Blanca (also known as Museo Casa Blanca ) was constructed in 1521 and served as the city’s earliest fortress as well as the home of its first Spanish ruling family. You might have heard of the man who made the search for the mythical Fountain of Youth his legacy, but before Juan Ponce de León took off on his chase for immortality, he built this home; his family and their descendants went on to live here for 200 years. The house provides a beautiful trip back through the ages and is definitely a historical highlight.

Discover the Old City's Nightlife and Dining Scenes

Marmalade Restaurant & Wine Bar

When it comes to the best lounges , bars, and nightclubs in greater San Juan, you'll find several of them in Old San Juan, a section of the island known for its active nightlife scene. Whether you prefer chic lounge vibes of upscale joints like Marmalade, grungy and funky bars like El Batey Bar, or multi-level discos (there are many to choose from), Old San Juan doesn't seem so old once the sun goes down.

Dining in Puerto Rico is also an incredibly rewarding experience, whether you're seeking local classics like mofongo , gourmet international cuisine, or a delightfully inventive fusion of Caribbean and global flavors. In Old San Juan, Calle de la Fortaleza (Fortaleza Street) has carved out its reputation as the city’s Restaurant Row, and is home to some of the best eateries in town; South Fortaleza, known as the SoFo District, even has its own biannual culinary festival. Of course, you don't need to restrict yourself to Fortaleza Street to enjoy good food in the old city, but the variety and quality of food options found here make it a good bet for a great meal.

Visit Legendary La Rogativa

Paul Downey / EyeEm / Getty Images

Of all the lovely sculptures in Old San Juan, why single out La Rogativa (the procession)? Because of the story of Puerto Rican patriotism it tells. The monument, located in Plazuela La Rogativa near the San Juan Gate, commemorates one of the most evocative legends of the island. When the British attacked Old San Juan in 1797, a quick-thinking priest took it upon himself to lead the outnumbered soldiers and civilians on a religious procession through the city. Apparently the British mistook the citizens’ prayer march for reinforcements and abandoned their attack. The sculptures recreate the moment as a work of art for all time.

Shop for Handcrafted Souvenirs

There's nothing wrong with a T-shirt or a shot glass, but if you want something creative and original to remember your trip by, the island is known for its lovely arts and crafts and you can find plenty of souvenir options throughout Old San Juan. From iconic vejigante masks found in numerous shops to the hand-carved santos (wooden figurines), souvenir shopping in San Juan is a real treat.

Browse the Old City's Art Galleries

Galeri­a Botello

Old San Juan is a haven for artists and proudly houses numerous art galleries that are well worth a look. Leading the list is the outstanding Galería Botello , but it's not the only place to feature fine local and regional works. Obra Galería, which showcases modern and contemporary art, is also worth your time.

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A Self Guided Walking Tour of Old San Juan

If you’re looking for an Old San Juan self-guided walking tour itinerary, you’ve come to the right place! Old San Juan is one of the most interesting cities in the USA.

Many cities in the United States have old towns. These can loosely be defined as colonial era towns that have kept their historical charm. There are quite a few scattered around the US. But perhaps the most spectacular of these old towns can be found in the US territory of Puerto Rico.

Old San Juan is the oldest – and in my opinion most beautiful – of all the historic old cities in the US. Founded by the Spanish in 1521, it’s a walking museum. Here we will cover a full day’s self guided walking tour of Old San Juan! 

Old San Juan – What You Need to Know

A brief history of old san juan, puerto rico , your self-guided walking tour of old san juan, avoiding the crowds in old san juan, eat like a local, outside old san juan , old san juan – faqs.

Note: this article contains affiliate links, which means that should you purchase something or get a quote through them I may make a small commission at no additional cost to you. This helps keep the site running with up to date information. I do not represent GetYourGuide, Booking.com, or Rentalcars.com. This is information only and not a recommendation to buy the product mentioned in this article.

Where is Old San Juan?

San Juan is the capital of Puerto Rico and located on the central north coast of the island. Old San Juan is the historic part of town, on a peninsula that juts out into the Caribbean Sea. Puerto Rico is an island between the Dominican Republic and The Virgin Islands and it’s about a 2 hour flight to the nearest spot of the mainland US.

How to get there

There are a lot of domestic flights into San Juan and a few international flights. Most major US cities on the east coast fly to San Juan. If your city doesn’t have a direct flight you’ll likely layover in Miami or elsewhere on the east coast. From the airport you can take a bus , taxi, Uber, or rental car to the Old Town, which is about 12km (7.5 miles) from the airport. 

If you’re combining a visit to Old San Juan with other destinations around Puerto Rico, it’s beneficial to have a car. You can use the search bar below to find a great deal on a rental in San Juan.

Parking in Old San Juan

If you’ve got your own wheels then I suggest parking in La Puntilla Parking lot . It’s right outside the old city walls and only $3 per day. It’s closed at night but there is free street parking at night nearby. It’s the perfect place to start your self guided walking tour of Old San Juan.

If you’re staying in the Old Town, though, your hotel might have parking included so be sure to check with your accommodation for parking options.

Puerto Rico speaks Spanish, but in Old San Juan just about everyone will be bilingual and speak English too. If you get outside of San Juan then you start running into places where the locals don’t speak English. 

Puerto Rican Food

Puerto Rico has its own unique cuisine. See the section below on Eat Like a Local.

Puerto Rico is part of the United States and uses the US dollar. Cards are accepted just about everywhere and it’s really not necessary to carry any cash, other than for parking lots and street vendors. San Juan is more expensive than you’d expect. It’s on par with smaller US cities in terms of the cost of everything.

You’d think with the GDP of Puerto Rico being lower than US states that things would be a bit cheaper but that’s not the case. It’s not as expensive as New York or Washington DC, but expect similar prices to midwestern cities.

Since you’re still in the US tipping is still a thing. You will be expected to tip at restaurants in San Juan.

Puerto Rico operates sort of like a state, but it’s not. It is a US territory instead, which means that US federal laws still apply, such as federal minimum wage and social security taxes, but citizens who live in Puerto Rico have no representation in the federal government.

They can join the army and go to war and die for the country, yet can’t vote for president. In 2020 Puerto Ricans voted by a slim majority to become a state, but it remains to be seen if that will ever happen.  

Weather in Old San Juan

Puerto Rico has a tropical climate and it’s hot and humid year-round. Summers are a bit hotter and rainier. San Juan is usually clear while the interior mountains are cloudy. You can reasonably expect San Juan to be hot, humid and sunny. 

You can also reasonably expect to get some rain if you’re there for more than a few days, so be sure to bring an umbrella with you on your trip.

Where to stay

There aren’t really any major hotel brands in Old San Juan. You’ll find a Sheraton on the south coast, but that’s really it. Old San Juan is full of small boutique hotels and holiday rentals instead, which adds to the charm.

They won’t be that much more expensive than staying outside the Old Town in one of the major brand hotels, but there are definitely more options and larger hotels outside. We stayed at Aloft San Juan but don’t recommend it due to loud music from the mall next door till well after midnight. 

Within the old town consider the 352 Guest House Hotel Boutique or the Casa Sol bed and Breakfast . Outside of the old town I like the Hyatt House or the Hyatt Place . They are right next to each other and It’s easy to get to the old town from there. Or check out all the listings on booking.com to find another great option!

Time of year to go

The peak tourist season runs from December to May. The weather is a bit cooler and drier. The summer months are the hottest and wettest but offer an experience with fewer tourists. The ideal time might be late spring to early summer. 

Just be mindful of when cruise ships stop in the port, because if you can avoid a cruise day that would be best. I explain how to avoid cruise days in a section below.

How long to stay in Old San Juan

It’s easy to see Old San Juan in one day. This self guided walking tour is structured around one day in the old town. A trip to San Juan should be combined with a beach vacation to Puerto Rico or a hike through the jungles of El Yunque National Forest, the only tropical rainforest in the US National Forest system.

Puerto Rico – “rich port” – was first settled in 1508 by the Spanish in a location outside San Juan’s city limits. A year later the settlement was moved to what is now San Juan and the name was officially added in 1521, which is the year the city is considered to be founded. Fortifications were built over the years and helped fend off numerous attacks, especially from the Dutch, French and English. 

For centuries it remained a small Spanish port city, never expanding beyond the original city walls. In 1898 the United States did what the Dutch never could and took Puerto Rico, thus ending the Spanish-American war. However, Puerto Rico did not become a territory until 19 years later. It has remained an American territory now for over 100 years. 

Over the years the colonial houses and buildings in Old San Juan degraded into a state of disarray. What you see today is the result of painstaking restoration of the old buildings that has taken place over the last 80 years. And they’ve done a hell of a job restoring the city to its original charm. These days Old San Juan is mainly a tourist destination. No more fending off invaders! 

If you’re curious what San Juan would have turned into had the Dutch taken over, then be sure to check out my complete guide to Amsterdam !

The Old Town is not large but there is a lot to see and do. Hitting all these spots will log 8-10 miles on your Fitbit. You can choose your own order of precedence, but hitting them in the order I have given below will make for happy feet. Check out the map below for the points of interest you’ll need to hit on this self guided walking tour of Old San Juan. 

The Colorful Streets 

Perhaps the main draw of Old San Juan is not one particular location, but the architecture of the city itself. The buildings are nearly all colonial-era Spanish architecture. The Caribbean has all sorts of old colonial-era cities, like the Zona Colonial in Santo Domingo or the Pietermaai district of Willemstad in Curaçao. But when it comes to colonial architecture, nothing beats San Juan.

This means cute balconies and colorful facades. All the streets are lined with charming houses of eclectic, bright colors. The old city itself is a UNESCO World Heritage Site. There is no single street to go for the best views. It depends on how many cars are parked and how crowded the city is. Rest assured there will be no shortage of photo ops on the streets of Old San Juan.

Castillo San Felipe del Moro 

Old San Juan’s most notable attraction is almost certainly Castillo San Felipe del Moro , the city’s original fort. This Spanish fortress was built over the centuries, starting in 1539. It’s an impressive structure and was used to fend off attacks, most notably from the Dutch in 1625.

These days the fort is part of San Juan National Historic Site, managed by the National Park Service. It was last used for military purposes during WW2 and since then has been solely a tourist site. It’s $10 per person to enter unless you have the NPS Interagency Pass or another yearly pass. 

The fort itself is an impressive structure. It rises seven stories from the water below and includes multiple fortifications and lookouts. It really reminded me of the beautiful ancient forts in Malta.

Allow at a bare minimum of an hour to visit the fort, but more if you want to walk along the coast along the promenade back to the Puerto de San Juan, the old city’s main entrance station. 

Castillo de San Cristóbal  

On the other side of Old San Juan lies another Spanish fort, Castillo de San Cristóbal . While not as well known, this fort is actually larger, the largest of its kind in the New World, i.e. the Western Hemisphere.

It was built about 100 years after San Felipe and meant to protect San Juan from land attacks. The two forts are connected by the old city wall that runs between them. 

Entrance to San Cristóbal is included with admission to San Felipe (and vice versa), so be sure to keep your receipt. It’s similar to San Felipe but has more viewpoints over land. This way the Puerto Ricans could see if the Dutch were gonna attack by landing somewhere else on the island and approaching on foot.

The two fortresses worked like a charm and Spain held on to Puerto Rico until it was surrendered to the United States in 1898. 

Catedral Basilica Menor de San Juan Bautista

The Catedral Basilica Menor de San Juan Bautista is the oldest church in the United States and the second oldest church in the Americas. While that might pale in comparison to some of the European gothic cathedrals, it’s still nearly 500 years old, dating back to 1540. I only admired it from the outside, but you’re free to walk in and have a look around. It’s not big and will only take a few minutes. 

Casa Blanca 

Casa Blanca is now a museum, but centuries ago this house belonged to famed Spanish explorer Ponce de Leon. It’s San Juan’s oldest house and contains many artifacts from the colonial days of the city. The house has some odd hours so consult the website linked above for the latest information. 

Puerta de San Juan 

Old San Juan’s original entry gate is found at Puerta de San Juan. It’s just an entryway in the city wall, but you can imagine old aristocrats arriving here hundreds of years ago. From here there is a lovely walk along the coast on the promenade. This takes you outside the city wall and eventually to the base of Castillo San Felipe de Moro. 

Situated outside the ancient city wall, La Perla is a former shantytown. Many years ago the slaves and lower class were forced to live outside the walls, thus La Perla was born. It’s full of colorful houses and right on the water, but you can tell the residents are not quite as rich as those inside the wall by one walk through the village.

It was also seriously damaged by hurricane Maria in 2017. Still cool to walk through though and your self guided walking tour of Old San Juan should definitely include a detour here. Just be careful at night, as there have been recent reports of violent crime aimed at tourists.

Musea de las Americas

If you’re into museums, or trying to beat the heat for a bit, pop into Musea de las Americas to learn a little bit about colonial life in Puerto Rico and see some artifacts from those days. 

Guided Tours

If you’d prefer to have a guide walk you around the city and add a bit of historic context onto your day in Old San Juan, then there are numerous short tours available with GetYourGuide , including walking tours as well as sunset cruises and sailing. You can even add on food tours, ziplining and all sorts of other adventurous activities. 

Make no mistake, Old San Juan can get pretty crowded. It’s not a huge area but it is an extremely popular place for American tourists. This is especially true on days when cruise ships dock at the port. The largest cruise ships can hold thousands of people. Now imagine all those people getting off at the same time and walking around Old San Juan.

If you’re not a part of one of these cruises then I highly recommend planning your trip to San Juan on a day where no cruise ships dock at the port. You can see which days have cruises using this link . About 500 cruise ships visit San Juan every year, and the vast majority visit between November and March.

In those months it’s very possible to have a day where three cruises stop at San Juan. And you absolutely do not want to be in town when three cruise ships are docked. So do yourself a favor and plan around the cruises. We were there on a summer day with no cruises and felt like we had the city to ourselves! 

For a small island, Puerto Rico has its own culinary culture. This isn’t intended to be a full rundown of Puerto Rican food but a quick synopsis on some of the main things to try. 

• Mofongo: the most Puerto Rican dish of them all. It’s essentially mashed fried  plantains served with some sort of meat. I’ve never seen it anywhere else in the world. It’s delicious. 
• Empanadas: Puerto Rican empanadas are fried and scrumptious. Don’t have too many though, as they are super unhealthy.
• Tostones and amarillos: deep fried green plantains and ripe plantains, respectively. 
• Arroz y habichuelas: red beans and white rice, served as a side with many meals. 
• Lechón asado: Puerto Rican succulent pig 
• Pastelon: Puerto Rican lasagna, made with plantains 
• Paella: this Spanish staple is found nearly everywhere in Puerto Rico 
• Flan: a vanilla custard cake. Simply amazing. 

Restaurants

There are tons of great restaurants in Old San Juan. Prices are in line with any large American city, and tipping is expected like anywhere else in the US. Most restaurants are indoors, as the narrow old streets don’t allow for much of a patio presence. You can find some rooftop bars and cafes though. 

To eat like a local, head to Cafe Manolin, a no frills ‘50s diner style restaurant with a huge menu. We had lunch there and dinner at Raices, which was recommended by the bartender at our hotel. It’s very popular and we waited over an hour for a table. But the stuffed avocado was excellent and worth the wait. The flan was also to die for. 

Some other restaurants that were recommended to us were Cayo Caribe, Cafe El Punto, and El Patio de Sam. Lastly, if you want to try the original pina colada, head over to Barrachina, where the drink was invented by bartender Ramon Portas Mingot in 1963. 

If you have longer in San Juan there are some more areas of the city that are worth checking out. Though I would say that I don’t recommend a beach vacation in San Juan city – even though there are plenty of beach resorts – due to the possibility of smoggy skies. It’s a big, dense city and you’re likely to get more beautiful skies further outside the city. 

Condado is the main beach area for San Juan. It’s lined with hotels and restaurants and worth a stop if you have a few days in San Juan. Pinky’s is a great spot for breakfast if you are in Condado.

In the Isla Grande region you will find a lot of new hotels (this is where we stayed) and a huge mall that has DJs every night in a common courtyard. Parque Isla Verde contains the airport and a long stretch of beach, as well as many 4 and 5-star hotels. 

The best beaches in Puerto Rico are well outside of San Juan. If you really want to see some amazing sand and water, take a day cruise to Icacos Beach on Cayo Icacos, a small island northwest of mainland Puerto Rico.

To get there you have to drive out of town quite a bit and take a boat to the island. There are tons of organized tours – like this one – so it’s not an issue getting there.

How long does it take to walk around Old San Juan?

Depending on your pace and how long you want to stop at the various sites, it could take anywhere from a few hours (no stops) to a few days if you stop to see everything. 

Do you need a tour guide for Old San Juan? 

No, you don’t need a tour guide for Old San Juan. This article explains how to do a self-guided walking tour of Old San Juan. If you want additional information on history and a knowledgeable local, having a tour guide can be beneficial though. 

Is one day in Old San Juan enough?

Yes, one day in Old San Juan is sufficient to see the highlights of the beautiful old city. 

Is it safe to walk around Old San Juan at night? 

Yes, it’s perfectly safe to walk around Old San Juan at night. It’s a happening place and there are people all over. Just see the next section about places to avoid. 

Where to avoid in Old San Juan?

After dark it’s best to avoid the La Perla neighborhood. Tourists have been known to get mugged and stabbed there in the wee hours of the morning. 

What is the difference between Old San Juan and San Juan? 

Old San Juan is a neighborhood of San Juan, a large city in Puerto Rico. “Old” comes from the fact that it was built in the Spanish colonial era. It’s the original San Juan. Since those days a sprawling metropolis has emerged from the old city, while the old city still retains all its colonial charm. 

Where do I park to access Old San Juan,

As discussed in the introduction, I suggest parking in the La Puntilla Parking lot when visiting Old San Juan. Cheap and right outside the city walls. 

Old San Juan is one of the most picturesque cities in the Americas. Walking the old cobblestone streets makes you think you’re in some historic European city. And if that wasn’t enough, the beautiful Spanish forts that protected the city for centuries really make you feel like you’ve landed in Europe. You’ll have a great time if you follow this Old San Juan self guided walking tour!

Chris Heckmann

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Walking Tours in Old San Juan 

Get to know the colorful old town with our knowledgeable guides, 24-hour full refund policy​​ cancel at least 24 hours before the tour starting time and receive a full refund. also, you can reschedule for another date for a small rescheduling fee.  easy going pace​ all of our tours are design for a pleasant walk. the speed of the tour is around 1 mile per hour (1.6 kilometers per hour). there's breaks along the way where you can seat to rest. ​ photo ops ​ we want you to create unforgettable memories of old san juan. for that reason, you will have time to take pictures along the way. feel free to ask your guide for help with pictures.  ​ small groups the maximum capacity of our tours is 20 participants. depending on the group size the guide could use an speaker so you do not miss any detail. certified tour guide  our local guides are knowledgeable about the history and culture of puerto rico. they are licenced by the puerto rico tourism company and are fluent in conversational english and spanish.  , our walking tours have:.

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All Tours in Puerto Rico

Take a look at all of our private tours in puerto rico.

Whether you’re interested in Old San Juan tours, heading into a rainforest, or relaxing in Puerto Rican hot springs, Private Tours of Old San Juan has something for everyone!

Don’t see the tour you’re looking for? Create your own itinerary with our customized tour and choose your own Puerto Rico tourist attractions! No matter where we go, I look forward to showing you our beautiful island.

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The Best of Puerto Rico in One Day – Private Tour

This tour focuses on the “must-see” sights in Puerto Rico. You will get a tour of Old San Juan (know the history and culture of Puerto Rico), El Yunque Rainforest (amazing), Maria de la Cruz Caves (impressive), Loiza (culture), Pinones (beach forest) and more.

• Up to 14 people
• Hour Glass 7 hours
• Tags All ages

• Hour Glass 7 hours or 10 hours

Customized Puerto Rico Private Tour

With this customized Puerto Rico tour, I will be your personal guide for a day! We can visit caves, lagoons, rivers, mangroves, coffee plantations, historic cities, archaeological sites, small towns, research centers, rainforests, among other places.

Private Wellness Tour: Waterfalls and Hot Springs in Puerto Rico

Waterfall tours in Puerto Rico are a must-do experience! We will explore some of the prettiest waterfalls in Puerto Rico. We’ll also go to the Coamo Hot Springs which many people consider to be the Fountain of Youth that Ponce de Leon was trying to find.

El Yunque Rainforest Wellness Tour

The rain forest is a great place to relax, take pictures and learn. But is more than that. Walking in the jungle (with the right consciousness) can help you grow, connect, get inspired and become a better person.

Atlantic Coast Full Day Private Tour

During this Atlantic Coast tour we will visit some of the best “off the beaten path” destinations like Cataño for great views of Old San Juan, Isla de Cabro, the statue of Christopher Columbus (largest in the Hemisphere), caves with petroglyphs, and La Boca, a beautiful black sand beach Puerto Rico has along the north coast.

Ponce Private Tour (from San Juan)

Ponce Puerto Rico is full of archaeological sites, museums, natural wonders, architecture and hidden gems. This tour can be customized to meet your requests. Take a tour from San Juan to the historical city of Ponce!

Rainforest and Hot Springs Private Tour in Puerto Rico

Have you always wanted to go on a Puerto Rico rainforest tour? Then come along with me and we’ll see rainforests, hot springs all while learning about Puerto Rican history, culture, geography and ecological features (birds, plants, etc).

• Hour Glass 4 hours

El Yunque Rainforest – Private Half Day Tour

Enjoy the best of El Yunque Rainforest in 4 hours.

Private Tours of Old San Juan operates under Special Use Permit from the USDA Forest Service on the El Yunque National Forest, permit number YNF22061.

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Rum Runners Craft Cocktail

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Eat. Drink. Explore.

Authentic Puerto Rican food tours with local cuisine & cocktails

Flavors Of San Juan™

The original Flavors of San Juan food tour. You’ll enjoy up to 5 restaurants/tasting spots while you see the real Old San Juan and learn about the “Fortress City’s” personality, rich history and interesting local tales.

• Rum Runners Craft Cocktail Tour™

Find out why they call Puerto Rico the Rum Capital of the world. Join us for a night of drunk history on our craft cocktail tour through the streets of Old San Juan. You’ll leave knowing a little bit more about why that rum in your drink is so special.

History Walking Tour

A smart and simple way to learn about and explore Old San Juan is with a local, knowledgeable guide who will lead you on an easy 2 hour history stroll through the oldest section of the city. Following the tour you will understand the…

El Morro Fort Tour

Bring your hat, water bottle and walking shoes on this expertly guided tour of Castillo San Felipe del Morro and learn how and why this fort was critical to Spain’s success in the region. We meet right outside El Convento Hotel so you’ll learn about Old San…

Have a special occasion you’d like to celebrate or simply want a little privacy? Planning your next corporate event? It’s time to do something out of the ordinary! Pamper your employees, partners, friends and family with an unforgettable tasty experience. 

Eat Well, Be Inspired

Join us for Puerto Rico’s original food tour of Old San Juan. We’ve been featured on CNN, the BBC, USA Today, Lonely Planet, and are ranked #1 food and walking tour in Old San Juan – trust you’re with the pros.

Passionate Tour Guides

Come as a valued guest, leave as a friend. Our passionate, local foodie guides eat, sleep, walk, talk, live Old San Juan and can’t wait to share it with you!

Tasty Foods, Hidden Gems

You didn’t come to Puerto Rico to eat a cheeseburger. Let us take you off the eaten track to show you the magic of adding pique to your arroz y habichuelas.

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Things To Do In Old San Juan

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Ever wonder why Old San Juan is a must-visit? Picture this: a compact, walkable city brimming with history, stunning architecture, and a vibe that’s both laid-back and buzzing with life. It’s the kind of place where you can explore centuries-old forts, enjoy the local cuisine at a street-side café, and soak in the views of a sunset that lights up the harbor. Old San Juan offers a blend of experiences that caters to the curious traveler, the history buff, and the foodie in all of us.

Do You Need A Passport to go to Puerto Rico?

Do you need a passport to visit san juan.

If you’re a U.S. citizen, the answer is no—you don’t need a passport to visit San Juan, Puerto Rico. Since Puerto Rico is a U.S. territory, all you need is the same identification you’d use to fly domestically. This typically means a government-issued photo ID, like a driver’s license or ID card.

However, if you’re traveling from outside the United States, standard international travel requirements apply, and you will need a passport to enter. It’s always a good idea to check the latest travel guidelines before your trip to ensure a smooth experience.

What is Old San Juan?

It’s the historic heart of San Juan, Puerto Rico, known for its well-preserved Spanish colonial architecture, vibrant blue cobblestone streets, and a laid-back yet lively atmosphere. Imagine wandering through narrow lanes lined with brightly colored buildings, stumbling upon hidden courtyards, and soaking up views of the ocean from ancient forts.

It’s not just about the sights, though; this place buzzes with energy from its cozy cafes, lively bars, and artisan shops. Essentially, Old San Juan is a blend of history, culture, and Puerto Rican flair, all packed into a walkable area that feels like a world of its own.

Historical Gems in Old San Juan

Puerto Rico has a rich and diverse history that is deeply ingrained in its culture. The island was first inhabited by the Taíno people before being colonized by the Spanish in 1493. The colonial legacy can still be seen in the architecture of the old town of San Juan, a UNESCO World Heritage site. In Old San Juan, you can visit impressive forts like El Morro and San Cristobal, stroll through colorful streets, and admire the colonial architecture.

Puerto Rico is also home to several museums and cultural institutions that showcase the island’s history and art, such as the Museum of Art of Puerto Rico and the Museum of the Americas. If music interests you, Puerto Rico played a significant role in the development of salsa with popularizing the Afro-Spanish music traditions of Cuba. Salsa music and dancing still play a significant role in the culture today.

Old San Juan Festivals

Puerto Rico is an island that knows how to party, and they know how to do it well. Some festivals are going on every month all year long. There are even festivals and celebrations that go on all year.

These festivals are highlighted with parades, music, food, drinks, and dancing. They are a convergence of Puerto Rican culture. The best months for these festivals are December and January, and daytime is the best time to experience them. At night, they tend to get a lot more crowded and rowdier.

Great Drinks

Puerto Rico is considered to be the King of Rum, and they embrace the moniker. There are amazing innovative mixologists! All over the island, they are using Puerto Rican rum and native fruits (like passion fruits, mangoes, papayas, and more) to create a perfect taste of Puerto Rico.

Many of these mixologists also compete internationally, so they are a lot of fun to watch work. There is everything from great drinks to beautiful paired drinks and courses, and you can find it all.

I took a food and drink tour recently and it’s definitely one of the best things to do in Old San Juan. I loved that you could tie so many things into one package, a historical walking tour, a couple tasty local dishes and some refreshing drinks! You can find the link to this tour here. Here are just a few photo’s of my day.

Bacardi Rum Factory

The Bacardi Factory in Puerto Rico is the largest in the world. This factory can bottle up to 100,000 bottles a day. Aside from just touring the factory itself, you can also go on a tasting tour.

This tour allows visitors to learn all about the rum, the bottling process, and the different flavors and tastes that Bacardi manufactures. It is an important part of Puerto Rico, and it is a lot of fun. I highly suggest you take an Uber, the fumes alone make it so that you’ll need a designated driver home.

The Food of Old San Juan is …Chef’s Kiss

The “Dining Capital of the Caribbean,” is the way that many Puerto Ricans refer to their homeland. Their cuisine is a harmonious blend of Taino (the native people of Puerto Rico), American, and Spanish cuisines. These different influences combine to generate amazing dishes like mofongo (mashed plantains) and Arroz con gandules y Lechon (rice with pigeon peas and pork). This is my go to!

Things to Do Outside of Old San Juan

The island has so much to offer that it might prove impossible to try to get it all in one trip. If you happen to want to venture outside of Old San Juan, you can check out my post on different locations to visit. You’ll find it here .

Here are just a few of my top recommendations.

Head Over To Vieques

Nestled just a few miles off the southeastern coast of Puerto Rico is the island of Vieques. The tiny island of Vieques offers visitors a rich history and a plethora of exciting activities to explore. Once used as a naval bombing range by the US Navy, Vieques is now a peaceful oasis with pristine beaches, bioluminescent bays, and lush wildlife reserves.

For those with a taste for adventure, hiking, snorkeling, and kayaking are popular activities. History buffs can explore the remnants of Vieques’ historic sugar plantations. And if you’re looking for a companion getaway, don’t worry!

Vieques is just a short ferry ride away from San Juan. If you are more adventurous, you can take a small plane. I don’t have the stomach for it!

But, if you’re looking for an island paradise that’s both rich in history and filled with excitement, head down to Vieques and experience all that this enchanting island has to offer!

Vieques is the home of a beautiful bioluminescent bay, and El Yunque is the location of the only subtropical rainforest in the United States. Below are my top three tours of El Yunque rainforest.

Don’t Forget Water Fun

No matter where you are going in the Caribbean, the beaches and ocean are an essential part of the trip. In Puerto Rico, areas like Culebra, Vieques, and El Yunque are great places to visit. Culebra is the perfect spot for snorkeling and scuba diving. Flamingo Beach in Culebra offers the ideal backdrop for your snorkeling and diving adventure. Below are a few of my top suggestions.

Which Things to Do in Old San Juan Will You Do?

Whether you’re a history enthusiast, a food lover, or a seeker of authentic experiences, Old San Juan offers something special for everyone. If you’re ready to turn this virtual adventure into a reality, our team of travel experts is here to craft a personalized itinerary that brings your dream vacation to life. Contact us today!

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