sunset cruise key west

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• Key West Wind & Wine Sunset Sail

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running.... Read More

• Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise... Read More

• Key West Sunset Champagne Cruise

Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy... Read More

• Key West Sunset Dinner Cruise

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar.... Read More

• Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran... Read More

Key West Schooner Sunset Sail with Hors D’oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and... Read More

• Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines... Read More

Key West Sunset Snorkel Sail

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and... Read More

Key West Dolphin Watch Sunset Snorkel Cruise

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous... Read More

Sunset Sip & Sail

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •... Read More

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Key West Private Wind & Wine Charter (for up to 30 guests)

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on... Read More

Key West Sunset Cruises Overview

A Key West sunset cruise is a vacation must-do that adds an unforgettable experience to any Key West visit. Choose a graceful sailing schooner, a sleek modern catamaran, or a roomy dinner cruise liner with live music and all the trimmings – this curated selection of the best Key West sunset cruises offers good times set against one of nature’s grandest spectacles.

Depart the harbor in the late afternoon to enjoy an evening on the water, or combine dolphin watching, snorkeling, or a glass-bottom boat tour with sunset and the perfect end to another day in paradise. Key West sunsets are famous for highlighting nature’s grandeur as the sun sinks below the broad ocean horizon and brings on dramatic color changes of a range and intensity not seen on land. The unobstructed fetch of the light, atmospheric moisture, and other refractory factors combine to produce awe-inspiring natural beauty.

Add a chilled beverage and a loved one to share the occasion and the result is sublime. Click on a selection below to learn more about the most popular Key West Sunset Cruises.

Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What type of boats are used for Key West Sunset Cruises?

A: The diversity of available sunset cruise vessels is one of the things that make Key West Sunset Cruises so special. Guests who enjoy sailing can choose a 65-foot skipjack schooner with authentic lines that replicate the sailboats used by 19th century Florida Keys fishermen and wreckers. Or a modern sailing catamaran with the stability, speed, and generous deck space these craft are known for. Power catamarans are fast and smooth, perfect watersports or dolphin-watching platforms. And of course, enjoying a buffet dinner and cocktails aboard a 65-foot custom party catamaran should be on everyone’s bucket list. For a wedding, anniversary, or other special occasion, try a private charter to have a sail or power yacht all to yourself.

All the boats used for these popular Key West Sunset Cruises are top-of-the-line designs built for safety, comfort, and fun on the waters around Key West. The United States Coast Guard regularly inspects every Key West Sunset Cruise boat, and all required safety equipment is aboard and properly updated at all times. This is luxury sunset cruising at its best, with expert local captains and crew members, high-tech navigation gear, and the latest in quiet, efficient, low-emission engines. Plus, there are those added touches to enjoy like room for cocktail and wine service, deck space for top local musicians to perform, and even a bit of space to dance on some cruises.

Q: What makes a Key West Sunset Cruise so special?

A: Something about sunset in a tropical island location inspires people to a greater appreciation for what is normally a simple daily event. The famous and elusive Waikiki sunset “green flash” draws hundreds of camera-toting tourists to the Kalakaua Avenue beach walk each evening. Maui has Mt. Haleakala, the “House of the Sun” with sunsets worth an hour drive up the mountain. Beach bar decks in Phuket Thailand get packed as early evening comes on. And sunset in Key West is definitely a big deal whether seen from land or water.

Mallory Square and the nearby anchorage waters have been a hub of activity in Key West for over two hundred years, and when hippies arrived in town during the late 1960’s, they discovered that Mallory Pier offered a perfect wide-open view to the west. The custom of celebrating the amazingly colorful ocean sunsets took hold, and now Mallory Square and the Key West sunsets are both world famous.

Visitors have been boarding boat tours out of the harbor near today’s Mallory Square since the mid-19th century. With quiet, unobstructed on-deck views, the blazing orange, red, and purple clouds along the horizon and the awesome disc of the sun visible as it slides out of sight captured attention very early on. Now, modern vessels are able to provide visitors with a nice range of specialized sunset-watching cruises to suit any taste, and the best way to find out why Key West Sunset Cruises are so special is to come aboard and try one (or more).

Q: Which Key West Sunset Cruise is best for me?

A: The only easy choice among the many popular Key West Sunset Cruises is deciding to go on one. After that, the variety of attractive options may easily lead a visitor to decide that the only solution is to enjoy more than one sunset on the water! But if a choice of just one (or two) must be made, the best strategy is to consider what you like best and who is joining you for what could easily be the highlight of any Key West visit.

Naturally, the idea of gliding smoothly over turquoise water under sail while toasting a perfect day with a cold beer, glass of wine, or cocktail is very tempting. A Sunset Sip & Sail or Premium Sunset Sail with Hors D’oeuvres and Full Bar will provide a perfect happy hour start for a couple planning an evening on the town.

For an active family, or anyone who enjoys the water, taking an afternoon snorkeling trip that winds down with a beautiful sunset (and beverages) offers the best of both worlds. A Key West Sunset Snorkel Sail is just the ticket. Nature lovers should try a Glass-Bottom Boat Tour Sunset Combo or take the Dolphin Watch Sunset Snorkel Cruise.

Looking to party with some reggae or just enjoy live music and a cocktail hour at sunset? Take a look at Rum n’ Reggae or the Sunset Party Cruise. The award-winning Key West Wind & Wine Sunset Sail is notable for its pairing of fine wines and craft beers with gourmet appetizers. Special occasions (and every Key West sunset is special) call for a Sunset Champagne Cruise or Dinner Cruise. And for the ultimate in luxury, gather family and friends or just one significant other on a 65-foot schooner and sail away on a Key West Wind & Wine Private Charter.

Q: What kind of wine is served on the Key West Wind & Wine Sunset Sail?

A: Looking for a sunset cruise with a focus on fine wine to go with the fine view? The Key West Wind & Wine Sunset Sail is a legend with locals and visitors alike. This elegant and awesome sunset cruise has pulled down top ratings on Trip Advisor for several consecutive years in addition to earning a Top Sunset Cruise designation (one of the top 2 in North America) from Coastal Living Magazine. The Wind & Wine is a cruise that stands above the rest because it is one of very few sailing excursions in the United States that offers a selection of “real” fine wines from America and around the world.

A small group will gather on deck beneath the billowing sails to enjoy an intimate atmosphere, tropical music, and the incredible Key West sunset along with 8 different wines from around the world and 5 types of domestic and imported beer. There are usually 4 red and 3 white wines plus a champagnoise open for the tasting. The charcuterie and cheese board goes far beyond simple sailors’ rations to deliver the perfect wine pairings with Dill Havarti, Smoked Gouda, fresh Mozzarella, and Brie cheeses. Caprese skewers, summer sausage, honey-drizzled green apple slices, fruit, water crackers and more make for the ultimate water-borne wine tasting session.

Q: Skipjack schooner or catamaran – which one is best for a sunset cruise?

A: Sailing schooners and sailing or powered catamarans are the two most popular Key West sunset cruise vessels. In fact, these are the most commonly used craft for all types of Key West water tours from Backcountry snorkeling and kayak tours to glass-bottom boat rides. The reason for this is simple – skipjack-style schooners and catamarans are both shallow-draft boats that are well-suited to navigating the sandbar- and reef-filled waters around Key West.

Skipjack schooners were originally designed for harvesting oysters in shallow Chesapeake Bay. Adopted for use by 19th-century Florida Keys wreckers, sailors who would race out to salvage cargo from ill-fated ships caught on the reefs around the Keys, skipjacks became very common in local waters as general working and fishing boats. Modern catamarans are adaptations of ancient Polynesian boat designs used by sea-going peoples who lived on tropical islands ringed by shallow coral reefs and lagoons. The ability to skim through the shallows and land directly on the beach was critical. Known for their stability and versatility, today’s catamarans are the fastest and shallowest-running boats on the water.

Both types of vessel provide a safe, comfortable ride and can take guests to the best places to sightsee and play in Key West waters. Do you enjoy a touch of history and the romance of a tall ship under sail? Then a schooner would be a good choice. These classic ships have been sailing out of Key West for over 200 years, and guests who come aboard a Key West schooner today are in for an award-winning luxury sunset cruise.

Catamarans also move very gracefully under sail, but a key difference is that the cat’s deck remains level at all times because the vessel does not heel (lean over under the wind power) like a single-hull sailboat. A catamaran can also offer more wide-open deck space between the two hulls. This allows for seating at tables, live music and dancing, and ease of movement around deck for enjoying the view and taking pictures. The broad, flat deck also makes the catamaran a great play boat for an afternoon of watersports and sunbathing.

Schooners and catamarans are both a lot of fun on the water, so the choice between them is mainly about a guest’s personal preference. Planned activities for the sailing trip as well as any physical limitations and the need for ease of movement should also be considered. Of course, many Key West visitors end up going out on both types of vessel to enjoy not only beautiful sunset cruises but the many other opportunities for fun on and in the water that have made Key West a world-famous tropical vacation destination.

Q: What are the best options for Key West Sunset Cruises?

A: According to verified reviews on Cool Key West and TripAdvisor, the best Key West Sunset Cruises are:

Q: What are the best kid-friendly options for Key West Sunset Cruises Activities?

A: According to verified reviews on Cool Key West and TripAdvisor, the best kid-friendly Key West Sunset Cruises are:

View all kid-friendly Activities →

Q: Which Key West Sunset Cruises have Instant Confirmation?

A: Key West Sunset Cruises with Instant Confirmation include:

View all Activities with Instant Confirmation →

Q: Which Key West Sunset Cruises have Free Cancellation?

A: Key West Sunset Cruises with Free Cancellation (in most cases up to 24 hours in advance of your activity date, check the specific activity page) include:

View all Activities with Free Cancellation →

Q: I need a ride! Which Key West Sunset Cruises include Hotel Pickup?

A: No problem. These Key West Sunset Cruises include Hotel Pickup:

View all Activities with Hotel Pickup →

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KEY WEST SUNSET SAIL with LIVE MUSIC

Come sail along on an ocean breeze and enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun. You’ll eat, drink and party the night away on Key West’s original live music sunset sail. So, grab someone’s hand and let the music move you as we chase down the world famous Key West sunset.

• Check-In, 5:30pm
• Departs, 6:00pm

Commotion On The Ocean Sunset Sail

Key West’s Original Live Music Sunset Sail

• Check-In 5:30pm
• Departs 6:00pm

Guests (Ages 4-10)

Guaranteed best price when you book direct.

Flexible & Refundable Reservations. Guaranteed best price when you book direct. *Seasonal discount restrictions apply.

• DEPARTURE POINT

Trip Features

• World-Famous Key West Sunset
• Hot & Cold Appetizers
• Private & Wedding Charters Available Learn More

What's Included

• Ice Cold Margaritas
• Draft Fury Lager, Michelob ULTRA & Seasonal Beer
• Wine (Chardonnay, Pinot Grigio & Cabernet Sauvignon)
• Sodas & Water

What to Bring

• Valid, Government Issued Photo I.D.
• Gratuities Customary

“ Commotion on the Ocean was a wonderful experience. The crew was absolutely fantastic! There was no need to worry about your cup ever being empty. The team was there before you could empty it to fill it back up. The ride was smooth, band was fantastic and the sunset was beautiful.”

This is a 10 out of 10!! It was an awesome day, professional, friendly staff all the way around! Thanks for a great day in Key West!

“ The crew, drinks and appetizers along with the live music made for a wonderful evening. Would definitely recommend Fury and Commotion on the Ocean to everyone!”

“ What a fun evening! The food was great, the band was great and the crew was even better; headed Captain Willie! I highly recommend Commotion on the Ocean, for a spectacular sunset cruise!!”

“ Commotion on the ocean was a great time. Fun music, excellent service, and beautiful views. Highly recommend!”

“ The Commotion On the Ocean was absolutely beautiful! Great music, dancing, tasty snacks, magnificent margaritas and an awesome catamaran! The sail ship was so much fun that we want to repeat it again once we return to Key West!”

“ This was our first Commotion on the Ocean and will most definitely become a must do every visit to Key West. EVERY staff person was over the top in customer service. Always smiling, taking care of any needs and best of all making sure your drink was always topped off. The food was plentiful and very good (loved the meatballs) And the live music was the perfect compliment to the entire experience. Great job Fury, I’ve ahead recommended you and will continue to do so!”

• Mojo Seasoned Chicken Tenders
• Shrimp Cocktail with Cocktail Sauce
• Fresh Vegetables with Ranch
• Jalapeño Cilantro Hummus
• Smoked Fish Dip
• Assorted Cheese & Cracker Platter

Chef’s seasonal selection of appetizers are subject to change

• Selection of Sodas
• Draft Fury Lager, Bud Light & Seasonal Beer

Menu Disclaimer

Unfortunately, we are not able to provide alternative menu items for those patrons who adhere to a specific diet or those susceptible to food allergies. Please feel free to contact us for details concerning our menu offerings should you have any questions. If you have any further reservations, we encourage you to bring a pre-packed meal of your own choosing.

BOAT FEATURES

• State-of-the-Art Catamaran (65ft)
• Large Seated Sundeck
• Shaded Lounge Area
• Modern Marine Restrooms

COMMOTION ON THE OCEAN KEY WEST SUNSET SAIL with LIVE MUSIC

Sail into the World Famous Key West Sunset aboard a FURY Catamaran!

Historic Seaport

Located on the corner of Greene St. and Elizabeth St.next to The Conch Republic Seafood Company.

• Commotion on the Ocean Live Music Sunset Sail
• Champagne Sunset Cruise

Double Dip Snorkel Trip

• Double Dip Combo
• Island Adventure
• Island Adventure Combo
• Ultimate Adventure H2.0
• Dolphin Watch & Snorkel
• Dolphin Watch & Snorkel Sunset Combo

Watching the sunset from shore is beautiful but a Fury Sunset Sail is a very unique way to watch the sunset while being on the water, listening to live music, hot and cold appetizers and unlimited drinks.

The sunset time varies every day throughout the year. But don’t worry, we will make sure you see the sunset before heading back to shore.

We serve a seasonal selection of hot and cold appetizers that include:

(Menu is subject to change)

Yes! We serve water, sodas, margaritas, champagne, beer and wine.

The live band is dependent by the day. The music is an eclectic mix of songs and styles. It is a wide range of popular cover songs. There is something for everyone to enjoy!

The exact location and route of your sail is dependent upon the wind and marine conditions. Your captain will choose the route that allows for the best view of the sunset. You will most likely sail by Mallory Square, Sunset Key and the Key West Harbor.

All of Fury’s sunset sail trips are family friendly. The Commotion on the Ocean has a very lively atmosphere. If you would like a more low key excursion, we suggest the Champagne Sunset Cruise or the Glass Bottom Boat Sunset Cruise .

There are three multiple viewing decks on the sailing catamaran.

Yes, but the space is limited in the shaded areas.

Fury Water Adventures does not operate in unsafe weather conditions, but a light rain shower is not a deterrent. The Captain will assess the weather and should the Captain determine that the conditions are unsafe to run the tour, the tour may be postponed or it will be canceled. If a trip is canceled by Fury Water Adventures for any reason, every effort will be made to reschedule the trip during your stay in Key West. If you are unable to reschedule, you will have the option of receiving a voucher for a future trip or receiving a full refund. Every effort will be made to run tours, as advertised. Should Fury have to amend or alter your tour due to extraneous circumstances, tickets remain non-refundable on tours taken.

Departure Location #3 631 Greene Street – Located on the corner of Greene St. and Elizabeth St. next to The Conch Republic Seafood Company.

No, we do not provide parking at any of our check in locations, but you can use street parking, pay to park lots or parking garages.

All cancellations must be made at least 24 hours prior to your trip’s scheduled departure time. To place a cancellation, please call 1-888-976-0899 or email [email protected] and refer to the confirmation number at the top of your confirmation document. Failure to place a cancellation at least 24 hours in advance will result in your credit card being charged the full amount of the reserved. No refunds will be issued for reservations cancelled within 24 hours of departure, unless reservation refund protection was purchased. Please note that failure to show for the reserved trip  without cancellation will result in no refund. If a trip is cancelled by Fury Water Adventures® for any reason, every effort will be made to reschedule the trip during your stay in Key West. If you are unable to reschedule, you will have the option of receiving a voucher for a future trip or receiving a refund.

Fury has a 24 hour notice cancellation policy to receive a refund. Guests can purchase Reservation Refund Protection for a 10% fee to be eligible to cancel or transfer tickets up to 1 hour prior to their scheduled departure. All you have to do is email a request to [email protected] no later than 1 hour in advance of your reservation time.

Reservation refund protection fees are 100% non-refundable in the event of any cancellation or reservation change.

Yes! Fury operates 365 days a year. Be sure to check out our Special Trips & Events page to see if we are running any special Holiday trips.

It is necessary for Fury to check you in and give you a boarding pass. This helps us maintain an accurate count for the coast guard. You may also be required to fill out various liability waiver forms for the activities you participate in.

No, we do not offer any wifi on our vessels.

Please bring a Valid Government Issued Photo ID. Gratuities are customary.

You may bring your own food and non-alcoholic drinks as long as there are no glass containers and it fits in a small soft cooler.

Yes! To receive a military discount on any Fury trip, please book through the MWR office on Key West’s Sigsbee base by calling (305) 293-4174. The ticket buyer must purchase tickets in person and present a valid Military Issued ID.

Most Fury tours will require the minor guest’s natural parent be present at check in to sign them in. Please call 888-976-0899 for specific policy details for your preferred tour.

Yes, life jackets are onboard for everyone in case of emergency.

Fury allows service animals only. A service animal is any dog that has been trained to perform tasks to benefit an individual.  The work performed must be directly related to the individuals disability.  According the ADA service animals for emotional support, therapy, comfort or companionship are not considered service animals.

The guest requiring the service animal must be in possession of the animal at all times. Due to the nature of Fury tours,  guest and service animal  may  be required to remain on the boat for the entirety of the tour . This is to ensure the guest’s safety as well as that of the service animal, Key West wildlife, other guests, captain and crew.

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Dolphin Watch Eco Tour

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• Departs 9:00am, 12:30pm & 5:00pm

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Glass Bottom Boat

Taking Visitors To Key West’s Reefs For Over 70 Years

• Departs 12:00pm, 2:00pm & 6:00pm
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Land's End Sunset Sail

Restrictions

• Amazing Key West Sunset
• A Romantic Atmosphere Aboard The Pelican, a Luxury Catamaran Yacht
• Delicious Hors D'oeuvres, Including Peel & Eat Shrimp
• Complimentary Sangria, Champagne, Wine, Beer, and Soft Drinks
• Full Liquor Bar

Ready for a romantic sunset aboard our luxury yacht? Best on Key West offers a relaxing and picturesque sunset cruise on one of our catamaran yachts. There’s plenty of room to sit back and enjoy the most beautiful sunsets that can only be seen in the Key West skies. We offer an intimate experience for this sunset sail, which means we limit passengers to half of the boat’s capacity. This gives you a cozier experience and a guaranteed perfect view of the blazing sunset sky while we sail peacefully down the coast.

A Sunset Sight to Behold

After a long day of watersport activities, shopping, and all of the other splendid festivities Key West offers, take our Land's End Sail and let the tranquil rocking of the boat help you  unwind. We invite you to sit back and enjoy yourself with complimentary chilled champagne, boutique wine, tropical sangria, premium beer and soft drinks. Our caterers also prepare and serve mouth-watering, chef-selected hors d’oeuvres including the area’s most delicious peel-and-eat shrimp.

This luxury sunset cruise leaves every afternoon from the Historic Key West Seaport. Our departure times are adjusted seasonally to ensure optimal viewing. We depart at 5 p.m. in the winter and at 6:30 p.m. in the summer, with check-in and boarding times 30 minutes prior to departure (exact check-in and departure times and details will be provided in a confirmation email). Sailing along the south shores of the island, you’ll have the best views of the coast and the sun hitting the watery horizon. 

This 2-hour sunset sail is a perfect way to end your Key West day. We invite you to experience the sunset in true Key West fashion with your loved ones, friends or your whole family. To watch the sun dip below the dark blue waters from a luxurious Best on Key West boat, all while sailing through the warm breeze along the southernmost point of the continental United States, is truly a spectacular venture. Don’t miss out on making some the greatest memories with the ones you love under the best views of the Key West sunset skies.

What is the weather cancellation policy? If the activity must is cancelled due to bad weather, and you cannot reschedule, you will be issued a full refund.

Where is the departure point for this tour? Check-in instructions will be included in your activity confirmation email.

Where can I park? There is metered parking available near the check-in facility.

It is your responsibility to make sure you are aware of and understand all restrictions pertaining to this tour before booking online or over the phone. It is your responsibility to ensure that you are medically qualified and within any limits listed below in order to participate in this activity. No refunds will be given to those who reserve a spot and can not participate due to the restrictions listed below. For more information please read our cancellation policy and terms and conditions page or call our staff with any questions regarding your ability to participate.

• 21 and over for drinking (must show valid picture ID)
• NOTICE : The discounted prices may not be available during Peak or Holiday periods. Peak/Holiday pricing is $69.95 per adult. 

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Sunset Sails/Cruises

Book Now Call to order 305-293-7245

Your Key West vacation is not complete without experiencing a Key West sunset sail! What better boat would you want to experience a magical Key West sunset other than the Schooner America 2.0?  From her experienced and professional crew to her comfortable and spacious seating, we think Schooner America 2.0 is the best Key West sunset sail our little island has to offer! Join us for a Key West sunset cruise aboard the legendary Schooner America 2.0, and make memories to last a lifetime!

Key West is famous for its sunset, and there is no better way to watch this stunning phenomenon than aboard the luxurious Schooner America 2.0 for a cruise in the emerald green waters. Enjoy some smooth Key West sailing with a refreshing beverage in hand and the wind in your hair for a Key West sunset cruise to remember.

Above all, our crew will cater to your every need on this Key West sunset cruise. Leave the hard work to us as we allow you to sit back, relax and enjoy cruising through the key West waters on this boat ride! 

On this boat ride, there is even a chance you may get a glimpse of the “green flash” as you watch the sun dip below the horizon. 

Not only is this sunset sail in Key West aboard the Schooner America 2.0 magical, but it is the most romantic and peaceful sail we have to offer. This sunset boat ride will not only create a memory that will last a lifetime, but it will keep you coming back to Key West over and over again. 

-->Key West Sunset Sail on Schooner America 2.0 -->

Enjoy the best sunset sail in Key West on the Schooner America 2.0!  Take in the vibrant colors of Key West’s famous sunset as you sip complimentary champagne.  On this Key West Sunset Cruise, you will magically glide through the crystal clear surrounding waters whilst being taken care of by our professional and friendly crew.

This two-hour Key West sunset cruise features complimentary champagne, wine, beer, soft drinks, and water and passed hors d’oeurves- veggie crudite, cheese and crackers, and shrimp cocktail. There is a cocktail bar on board for purchase. Sit back and relax while Schooner America 2.0 plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience!  (Call us directly to save 6% online processing fee)

-->Champagne Sunset Valentine’s Day Sail -->

Join us for our Key West Valentine’s Day Sunset Sail aboard the Schooner America 2.0!  This is a day to celebrate your loved one.  So spend Valentine’s Day in Key West aboard our elegant Schooner. It truly is the perfect way to show your love and appreciation. Sail through Key West with a glass flute of French champagne in hand and cruise aboard our classic boat for an evening of elegance.  Watch the sun dip beyond the horizon.  Snuggle up with your loved one to celebrate your love for each other.  Reflect on your relationship aboard this Valentine’s Day cruise.Our professional crew will cater to your every need. We will wine and dine you and make you feel like royalty. Key West sailing is a magical way to capture a moment in time.  So what better cruise to do this on then the Key West Valentine’s Day Sunset Sail.  This magical Key West sunset sail will take your breath away and your loved one will be swept off their feet all over again.  (Call us directly to save 6% online processing fee)

-->Full Moon Sail Aboard Schooner America 2.0 -->

Sail through the Key West waters by full moonlight on this romantic Full Moon sailing adventure aboard one of Key West’s most stunning modern sailboats, the 105 ft Schooner America 2.0. This special sail is only offered for a limited time every month! Ticket price includes 1.5 hours of sailing, complimentary soft drink, and water. Drinks and snacks available for purchase. Pro Tip:  Call us directly at 305-293-7245 to avoid the 6% online processing fee.

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🌅 The 7 Best Key West Sunset Dinner Cruises [2024 Reviews]

Key West is one of the most beautiful places not only in the United States, but in the entire world. It makes sense, then, that tons of tourists flock here every year.

The natural beauty and incredible climate that stays consistent pretty much year-round makes it a great place to hang out outdoors. The natural landscape, ocean, and electric sun come together for gorgeous sunsets every night, and there are many great places to watch them.

However, nothing compares to one of the top Key West sunset cruises, which we’re here to bring you today!

Best Sunset Cruises in Key West

Quick answer: the 7 best rated key west sunset sails for 2024.

• Key West Sunset Sail Aboard Schooner
• Small-Group Key West Sunset Sail with Wine
• Key West: Sunset Cruise with Buffet Dinner and Open Bar
• Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres
• Key West Sunset Cruise with Live Island Music
• Sunset Sail Cruise in Key West
• Key West Sushi Sunset Cruise

Key West Sunset Cruise Reviews

1. key west sunset sail aboard schooner.

• Duration: 2 hours
• Departure: 202 William St, Key West
• Departure Time: Varies by time of year
• Includes: 2-hour sailing experience aboard America 2.0, complimentary beer, wine, champagne, soda, individually-plated hors d’oeuvres

If you want to feel like you’ve gone back in time almost 200 years, then you have to check out first tour out! The Key West Sunset Sail Aboard Schooner tour will take you over the beautiful ocean on a replica of the 1851 Schooner America.

This smooth ride is luxurious, a load of fun, and one of the best ways to watch the sun go down on the island. Meet up around 4 pm along with the rest of your group to board the ship. You’re immediately greeted by the crew, who are super friendly and make the experience that much better.

Once you take a seat (or stand if you prefer), you’ll be served with complimentary hors d’oeuvres along with a nice selection of alcoholic and non-alcoholic drinks.

This is a great way to meet other tourists or locals, bring the entire family on board, or simply experience it with your significant other.

Set sail, enjoying the sounds of the water underneath the ship as you head towards Mallory Square. There are a ton of people who come to the square to watch the sunset – wave to them from the ship!

Next, you’ll sail by the famous Fort Zachary Historic State Park, which has its own unique history and looks impressive from the water! At this point, the sun will start going down. However, not before you reach the incredible views that Sunset Pier has to offer!

The neon orange reflects wonderfully off the water, and the music and other people nearby just makes it that much more magical.

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience, 2. small-group key west sunset sail with wine.

• Departure: 255 Front St, Key West
• Departure Time:  Varies by time of year
• Includes:  Unlimited beer, wine and soft drinks, wine tasting, light refreshments

Are you a lover of wine and/or beautiful sunsets on the water? If you are, then you’re the perfect guest for the Small-Group Key West Sunset Sail with Wine Tour ! This is a bit more of an intimate cruise, where the one prior to this was made for the larger crowds of people.

Make sure to check in approximately 30 minutes before the departure time the crew advises you of, ensuring everyone gets on board and comfortable. We found the crew to have incredible attention to detail, and were very friendly, putting safety at the forefront of the operation.

Once you board the 65-foot schooner, you’ll realize that there’s plenty of seating room, and you won’t be squashed in with other passengers.

Once you set sail, you’ll be served a choice of wine, 4 different kinds of beers, along with delicious charcuterie selections such as a wonderful cheese, cracker, meat, and olives plate.

Rest assured the crew will keep the wine flowing with 8 different selections available! We personally enjoyed the summer sausages, brie, and green apples with honey, however, there really is something to suit any taste.

If you’re looking to plan a fantastic date night with your other half, this is really the way to go due to the smaller group sizes and alcoholic beverage selections against a stunning background.

Watch the sun go down over the horizon of endless shimmering water, with the sun reflecting off of it. This creates an orange glow that looks almost unreal at times. Make sure to take out the camera for some excellent photo ops!

3. Key West: Sunset Cruise with Buffet Dinner and Open Bar

• Departure: 201 William St, Key West
• Includes:  Buffet dinner, o pen bar, l ive music, s unset cruise

Who doesn’t love endless food and drinks? If you’re enjoying a wonderful vacation in Key West, you shouldn’t have to limit yourself and try everything that catches your eye. On the Key West: Sunset Cruise with Buffet Dinner and Open Bar tour, you don’t have to!

This is yet another 2-hour, intimate cruise with smaller group sizes. With that being said, if you’re going with a significant other, it’s a great date night option. However, just as well, it’s a fun time for the entire family though it tends to lean more towards adults.

Are you looking for a calm, relaxing cruise tour instead of a party cruise? There are plenty of both in Key West, and this one falls into the category of the former, despite the ship being called “The Party Cat”.

The smooth ride on the ship along with the chill music makes for a serene way to enjoy the afternoon.

Once you board, enjoy a buffet comprised of fresh tropical fruit and dishes. You can expect options such as: roast pulled-pork in mojo sauce, deep-fried sweet plantains, black beans and rice, grilled chicken, friend fish, mixed veggies, pasta with mini shrimp, along with Cuban bread and butter.

Drinks are also delicious, with endless margaritas, rum runners, champagne, beer, wine, and spirits. After dinner, head upstairs to the upper deck to groove the night away to some live music!

The local musicians are very talented and entertaining, setting the tone for a fun evening as you watch the sun set with the electric colors spreading across the sky.

4. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres

• Departure: 205 Elizabeth St , 205 Elizabeth St, Key West
• Includes: Beer, wine, champagne, sangria and soft drinks, chef’s selection of hors d’oeuvres, full liquor bar included, live music from local Key West musicians

If you’re on the hunt for an amazing sunset cruise but are on a budget, put this one at the top of your list! The Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres is all that and more.

Oh, but it’s not just a cruise! It’s a 2-hour excursion where you get to try a little bit of southern flavor with peel-and-eat shrimp and an upscale twist with fresh hors d’oeuvres. If you want to escape the crowds that gather on shore to watch the sunsets, we can’t think of a better way to do it!

Meet up at the tour office located between Conch Republic and Schooner Wharf 30 minutes before the departure time (around 4 pm). Board the sleek, 60-foot catamaran that sports a whopping 1,500 feet of deck space!

With smaller group sizes, everyone has more than enough room to walk around and mingle, or kick back and relax.

The crew is incredibly friendly, and always attentive and there to make sure everyone has a great time. Once you board, you’ll be able to revel in amazing live entertainment, and all-you-can-eat drinks and snacks.

Yep, you read that correctly! The music does vary, but typically you’ll have some jazz and smooth music to accompany you. Drinks consist of beer, soft drinks, sangria, full liquor bar, wine, champagne, and more.

As the sky starts changing colors, you’ll cruise by important landmarks along the coast, such as Mallory Square, Navy Mole Fort Zachary Taylor Historic State Park, and more. Make sure to take your camera out to take some photos of the blue waters meeting the orange sky!

5. Key West Sunset Cruise with Live Island Music

• Departure:  631 Greene St , 631 Greene St, Key West
• Departure Time: 4 pm
• Includes: Appetizers, dishes, alcoholic beverages, soft drinks

Does dancing to some island grooves from local musicians while you eat, drink, and enjoy a beautiful sunset on the water sound like a good time to you? Then give the Key West Sunset Cruise with Live Island Music a good look! This is yet another cruise that’s easy on the wallet and a couple of hours of good vibes.

From the very get-go, it’s an awesome experience thanks to the attentive and friendly staff, and positivity all-around. We should let you know that this is kind of a more upbeat experience than the others, which have a more relaxing setting.

The band plays everything from reggae to rock, and the crowd can get a bit lively! However, it’s a ton of fun! The crew will escort you onto the spacious catamaran, which is clean, and looks to be quite new.

There’s ample seating everywhere, aside from the large dance floor so you can bust a move without worrying about anyone getting in your way!

Enjoy unlimited appetizers, beer, margaritas, wine, sangria, champagne – whatever you feel like having! There are plenty of soft drinks and water available as well, if you don’t want any of the other options.

Enjoy cruising along the calm waters as the sky turns pink, orange, and yellow, reflecting off of the ocean. You’ll get to see Mallory Square, Sunset Key, and Key West Harbor as you sail along.

This is a very welcoming experience, with a lively atmosphere that’s perfect for guests of all ages! However, it may not be ideal for children who do not like loud music as this is a live band. It’s a great way to dance a little, enjoy cruising along, and have some appetizers while being back just in time for dinner!

6. Sunset Sail Cruise in Key West

• Departure Time: 4:00 pm
• Includes:  Sunset sail, snacks, coolers of ice with cups and bottled water

Next up, we bring you the Sunset Sail Cruise in Key West , which is a crowd favorite. Have you ever thought that being a pirate may be fun? Well, then this tour should immediately hit the top of your list because you’re about to get as close as possible to that!

We’re sure there’s no other Key West sunset cruise like this one, as you’ll be riding on the island’s most photographed ship? Why does it hold this title?

Because the Schooner Jolly II Rover is the only squared-rigged, topsail schooner in the Historic Seaport! You may have heard of it referred to as the island’s famous “Red Sails in the Sunset” tall ship!

If sailing catches your interest, you’ll love how interactive this cruise is. You’ll be able to help raise the sails, steer the ship, and “shoot the cannons”. However, it’s never obligatory. You can be as involved as you want, no pressure.

The crew is one of the friendliest we’ve encounters, which is really saying something! It’s not uncommon for the ship’s owner to come out and visit with everyone, either. The crew will give an interesting historical account of the ship, the area, and much more.

As you sail, make sure to take advantage of the unlimited snacks and ice-cold water onboard. On here, you won’t be hearing any music or rowdy environments. This tour is designed to be peaceful and allow you to take in the experience of sailing while enjoying the natural beauty around you.

You’ll cruise into Man O’ War Harbor, see Christmas Tree Island, mansions on Sunset Key, Mallory Square, Navy Mole, and Fort Zachary Taylor!

7. Key West Sushi Sunset Cruise

• Departure:  Barefoot Billy’s Boat Cruises – Garrison Bight Marina , 719 Palm Ave, Key West
• Includes:  Alcoholic beverages, bottled water, soda, snacks, restroom on board

You’re probably already aware of the fact that Key West has some of the best seafood in the United States. This means that there’s a ton of good sushi offered on the island as well. If you want to enjoy some delicious sushi rolls while watching the pink sunset electrify the water and sky, check out the Key West Sushi Sunset Cruise !

This boat is one of the smallest ones of any sunset cruise we’ve seen in Key West, however, this offers a more intimate experience that’s great for sharing with your loved one(s). The captain and crew do a great job of keeping you entertained while making sure everyone is tended to properly.

Once on board, you’ll be served platters of sushi so make sure you save some room! This is a great way to get to try different types of rolls that you haven’t had before. There are plenty of other snacks and many beverages available as well, just in case someone in your group isn’t a sushi fan.

Even if you are bringing the entire family, there’s enough fresh food for everyone with everything cooked to perfection!

While the captain tours you around, they’ll share many stories, personal anecdotes, and historical accounts that will have you at the seat of your chair!

Cruise by Mallory Square, Fort Zachary Taylor Historic State Park, Key West Lighthouse and Keeper’s Quarters Museum (seemed to be most peoples’ favorite), and the incredible Southernmost Point.

This is the lowest latitude land in the contiguous North American States so make sure to get a photo or two!

Why You Should Take a Dinner Cruise in Key West

Taking a Key West dinner cruise, especially at sunset is a great way to experience the beauty and charm of this unique island in Florida.

• Scenic Views : Key West dinner cruises have awesome views of the sunset, the coastline and of course the ocean. You can enjoy the stunning natural beauty of the area while enjoying a meal.
• Unique Experience : A dinner cruise in Key West is a unique and memorable experience, especially if you are celebrating a special occasion like an anniversary or birthday. It is a romantic way to spend an evening with a loved one or a fun way to enjoy time with friends and family.
• Delicious Food : Most Key West dinner cruises offer a variety of delicious food options. It will range from fresh seafood to traditional American cuisine. Most cruises include live music or entertainment during and after dinner.
• Convenience : A Key West dinner cruise is a very convenient way to enjoy an evening out on the water without the hassle of navigating the island or finding parking. Some cruise operators even include transportation to and from the boat.
• Historical and Cultural Value : Key West has a rich history and culture. Some dinner cruises offer educational and informative commentary from the boat captain about the area’s history and landmarks. This is a great way to learn more about the island while enjoying dinner.

Entertainment

The Key West Sunset Sail Aboard a Schooner is our Editors Choice for the best Key West sunset cruise

Robert Baker

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The 8 Best Sunset Cruises in Key West (2024)

What better way to experience the majestic beauty of the Florida keys than by enjoying some of the best sunset cruises in Key West. Enjoy a fantastic Key West sunset with live music and bottomless booze with several different sunset cruise operators to choose from.

There are plenty of options for the best sunset cruise in Key West, with many providing drinks, snacks, or dinner as you take in the sunset. The most popular options are watching the sunset on a catamaran, listening to a live band, hoisting the sail and enjoying the best of Key West. 

Top Pick: Key West Sunset Cruise

Don’t miss one of the highest-rated Sunset Cruises in Key West with over 2000 positive reviews and our top choice of the best sunset cruise in Key West !

Meeting Points & Information

• Most of the Key West sunset cruise meeting points are Key West Historic Harbor or near Conch Republic . 
• The minimum drinking age is 21 years old . 
• The time of sunset in Key West varies throughout the year, but you can expect boat departures between 6 pm and  8 pm. 

1. Key West Sunset Champagne Catamaran Cruise

4.5 Stars (449 Reviews)

Sebago has operated its Key West Sunset Champagne Catamaran Cruise for a number of years and is one of the top-rated Key West sunset cruises. Experience a 69-foot catamaran with an open bar that includes views across the Gulf of Mexico & Atlantic Ocean.  

The hugely popular tour offers a hugely enjoyable Key West cruise experience, with a fantastic crew and captain who are eager to answer questions and point out sights of interest. Savor the spectacular sunset with either a beer, glass of champagne, wine or sangria. 

Included in the tour: 

• Unlimited wine, beer, soft drinks
• A modern catamaran
• Tour length: 1 Hour & 30 Minutes – 2 hours. 

What Guests Said:

“I had an absolutely amazing time! The views were breathtaking, the crew was exceptional, and the overall ambiance was magical. The sunset was a sight I will cherish forever. I highly recommend this cruise to anyone visiting Key West. Thank you for providing such a remarkable experience!” Joonhyeong_P

2. Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

4.5 Stars (372 Reviews)

Enjoy a cruise on a spectacular Key West catamaran with departures either in the morning or late in the evening for a sunset cruise.

The Key West Dolphin Watch Sunset Sail is an intimate sunset cruise that sails past the landmarks of Key West and takes in stunning views of Fort Zachary Taylor , as well as spotting wild dolphins in the Gulf of Mexico. 

Enjoy the Key West sunset from the catamaran as you enjoy freshly prepared tapas and snacks. This Key West sunset cruise is perfect for anyone looking to sit back and relax, perhaps even spot dolphins and enjoy conversation with fellow passengers. 

Included in the tour:

• Small Groups
• Departures from Key West Historic Harbor
• Tour length 2 Hours 30 Minutes

Price of Cruise: $92 per person. 

“ Aside from the amazing sail, the chats with the crew and other passengers was really an added highlight. We love being on the water and sunset did not disappoint – we also got to see some dolphins, but, being able to talk to the entire crew and some passengers really did add to the overall experience. Highly recommend this experience. Captain Rachel was phenomenal and we thoroughly enjoyed it .”

3. Key West Premium Sunset Sail aboard Schooner with Hors D’oeuvres and Full Bar

5 Stars (442 Reviews)

Unlike several of the other Key West sunset cruises which take place aboard a catamaran, sailing on a classic schooner is a completely different experience . 

The classic schooner offers visitors a romantic vessel to enjoy watching the spectacular Key West sunset. With gorgeous hors d’oeuvres provided as you sail around iconic Key West landmarks such as Mallory Square which also happens to be the birthplace of watching sunsets in Key West. 

Take in the sights and even help the crew hoist the sails on this classic Key West Schooner .  The romantic sunset cruise on Appledore Star is one of the best sunset sail Key West tours.

Included in the Key West Sunset Cruise:

• Tasty finger food
• Hoist the sails with the crew
• Tour length: 2 hours

What Guests Said:  

“Great crew, just the right amount of time and beautiful sunset. The hors’d ‘oeuvres were tasty and lots of drink options. Champagne at sunset was my guilty pleasure! We’ll book again next time we visit!”

4. Key West Sunset Cruise with Tropical Buffet Dinner

4 Stars (961 Reviews)

Spend your late afternoon enjoying the infamous Key West Sunset with a tropical buffet dinner . The menu changes regularly but can expect to find typical dishes that are influenced by the region, such as black beans and rice, or Caribbean roast pork . Don’t miss trying the plantains!

With the weather in Florida sometimes being overwhelmingly hot, you can relax in the large open cabin that is able to fit 60 people comfortably with AC . When you’ve finished dining on the scrumptious buffet dinner, head to the deck, listen to the live music and enjoy the incredible sunset. 

With an open bar that includes mojitos, what better way to enjoy one of the best sunset cruises in Key West than by sitting on a 65-foot yacht and making new memories. 

• Tropical buffet dinner
• Air Conditioning
• Spectacular Key West sunset views

Price of Cruise: $88

“The food was amazing!! The service outstanding! Entertainment was great and funny! The performer engaged the crowd and was family friendly.”

5. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres

4.5 Stars (2229 Reviews)

One of the top-rated and best sunset cruises in Key West is the Key West Sunset Sail with Full Bar and Live Music. Set sail in the late afternoon and enjoy terrific live music, a full open bar, and plenty of delicious hors d’oeuvres. 

It also happens to be one of the busiest booze cruises in Key West that has a solid reputation for its energetic crew and entertainment. Dance the evening away while enjoying a full open bar that includes beer, sodas, wine and sparkling wine. 

The hors d’oeuvres are tasty finger food staples such as egg rolls, shrimp and other great food for soaking up all the booze!

With live commentary and information about the island of Key West, the Key West cruise takes in the landmarks of Key West and one of the most spectacular sunsets in the Florida Keys. 

• Hearty snacks

Price of Cruise: $80

“Live music, good appetizers and great crew! We had a blast! We’d do it again and recommend to anyone especially couples.”

6. 2-Hour Private Sunset Cruise around Key West

4.5 Stars (46 Reviews)

Want to escape the crowds and charter your own private sunset cruise in Key West ? Then Blue Chi Charters offers an incredible and intimate experience. Experience the incredible Key West sunset with just your loved ones, as you spend 2 hours passing by the iconic Key West landmarks. 

Savour the privacy and experience Key West without the crowds, as you head to points of interest like the Southernmost Point in the USA, or uninterrupted views of Fort Zachary Taylor State Park & Mallory Square. 

You can enjoy your private sunset cruise in Key West with complimentary beverages. You can also bring your own bottles of wine and beer on board as they have an ice cooler. 

• Private Charter Boat
• Bottled Water

“I took my significant other for a private, romantic cruise into the sunset and we had a wonderful time on this two hour ride around Key West. Our Skipper was very knowledgeable and kind, he provided interesting insights at just the right moments without being intrusive. It was a truly romantic and memorable experience that ended with a spectacular sunset.”

7. Key West Sunset Snorkel with Unlimited Draft Beer & Wine

4.5 Stars (76 Reviews)

Set sail and explore the incredible crystal clear waters of Key West, stopping off for snorkeling and swimming in the waters of the Atlantic Ocean . Experience the magic of the coral reefs that are abundant with marine life. 

Spend the hours before sunset swimming the 3rd largest natural reef in the world, the Florida Marine Sanctuary. Keep your eyes peeled for turtles, reef fish and you may even spot a wild dolphin!

Back on board, enjoy the amazing Key West sunset with a nice cold beer or glass of wine as your dry off. This is one of the best sunset cruises in Key West for visitors looking to swim and enjoy a spectacular sunset.

Included in the private catamaran:

• Snorkeling equipment
• Open water snorkeling in a coral reef

Price of Cruise: $60

“The crew made the experience easy and super enjoyable. The tour isn’t crowded and comfortable. Definitely recommend this one out of all the tours in Key west!”

8. Sunset Tiki Boat Tour in Key West

5 Stars (93 Reviews)

If you are in Key West with a group of friends, what better way to enjoy the amazing sunset in Key West than by renting your very own Tiki Boat ? 

Bring your own booze as you and your friends set sail on a tiki boat complete with a tiki bar! 

“What a great night! Very fun to be on the water on this boat! Nick the captain was personable and fun! We brought our white claw and snacks! We will book this again!!”

A Key West Sunset Cruise You Won’t Forget

Why not take the hassle and claustrophobia out of watching the Key West sunset by taking a splendid and squish-less experience of a fabulous Key West sunset cruise?

Drop a comment below and let me know which of the best sunset cruises in Key West you ended up choosing and how it was! Continuing on your Florida adventure? Make sure to check out my post on the best rooftop bars in Tampa .

Pin for Later!

Meet Missy…

Missy spent the first 2 decades of her life living in her native Dublin, Ireland. Before a life living overseas called to her, and she spent the next decade living in China, Laos & Belgium. She now splits her time in Antwerp, Belgium, and wherever the sun is currently shining. You can follow Missy’s real-time travels on her Instagram .

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ULTIMATE Guide to the Best Sunset Cruises in Key West

If you are planning a Key West vacation, you might wondering what you should in the evenings. In my opinion, one of the best things to do in Key West is go on a sunset cruise. In fact, Key West sunsets are so legendary, they have a nightly festival to watch them from Mallory Square.

Luckily, there are tons of different sunset cruises to choose from! In this post, I’ll answer all your burning questions about sunset cruises in Key West, like how much they cost, how long they are, where to book, and more!

Plus, I’ll provide a list of the 9 best sunset cruises in Key West , which are each unique and have something special about them!

Of course I also recommend watching the sunset cruise on land at Mallory Square one night. But experiencing the sunset from the water is one of those magical things that just can’t be beat! Listen to island music, eat delicious seafood, and let your worries fall away as you watch the sun dip into the sea!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you! 

A Complete Guide to the Best Sunset Cruises in Key West

Frequently Asked Questions About Key West Sunset Cruises

Before we get into the list, first let’s talk about some things you need to know before going on a sunset cruise in Key West! From what to wear to when to go, preparing for your sunset cruise will make sure you have the best experience!

How long are Key West sunset cruises?

Most of the sunset cruises in Key West last around 2 hours – some a little less, some a little more. Surpsingly, most of the ones that include dinner last 2 hours as well. More on that later!

Where do Key West sunset cruises leave from?

Almost every single sunset cruise in Key West will leave from the Key West Historic Seaport shown in the map below. This seaport is just outside of historic Old Town, so if you are staying nearby, walking shouldn’t be a problem.

When you book a tour, they will give you an address and meeting point. Most of the tour companies have small booths around the marina where you can check in, and then they will give you more detailed instructions on which boat to get on!

Pssst : Planning a trip to Key West? Don’t forget to check out my Ultimate Florida Keys Travel Guide for more information on how to get there, where to stay, things to do, and other trip details!

What time do Key West Sunset Cruises Depart?

The answer is… it depends! What time your cruise departs will depend on which tour you choose and what time of the year you are visiting! For example, in the summertime, sunset may not be until 7-8pm, so you can expect the cruises to leave around 6-6:30pm.

However, in the wintertime, the sun sets much earlier, so cruises may leave as early as 4:30pm! You can use this website to check the exact time of sunset on a specific date.

If you’re taking a longer sunset cruise, like this one that also includes snorkeling, you will probably leave even earlier to allow time for the additional activities!

How much do Key West sunset cruises cost?

You can expect to pay between $50 – $100 per person for a sunset cruise in Key West. However, similar to the above, it really depends! Check out the next section where I jump into this a bit more.

What’s included in the price?

Every sunset cruise is unique in what they offer and how much they cost! For example, some of the cruises include full buffet dinners, which are going to be closer to the $100 per person range. Some cruises offer unlimited alcoholic drinks and no food, while others offer passed appetizers in addition to the drinks! Most of them will also have live music, which is a huge plus!

What should I wear on a sunset cruise?

Sunset cruises in Key West are pretty casual affairs. I’ve seen people in jean shorts and flip flops, but most people dress in resort casual.

For women, remember that it will be windy once you’re out on the water, so I don’t recommend skirts or dresses that can blow up easily! Also, leave the high-heeled shoes at home.. you won’t need them on a boat.

For men, anything from shorts and a t-shirt to jeans and a polo is acceptable. I would expect most men to be in shorts – you are in the Keys after all!

Make sure to check out my guide on What to Wear in Key West for even more packing tips, plus a free printable!

What’s the drinking age in Key West?

The drinking age in Key West is 21 years old. However, that does not mean you have to be 21 to go on a Key West sunset cruise! Almost all of them allow children and minors. Just expect to be carded if you are planning to drink!

What else is there to do in Key West?

Short answer: so much! If you’re planning a trip to Key West, you probably already know how many incredible activities there are to choose from. If not, you can check out my blog post on the Top 25 Things to Do in Key West !

My biggest tip? Get out on the water! I recommend a Key West snorkeling tour like this one .

Top 9 Key West Sunset Cruises and Which to Choose

Alright, now that we’ve answered all of your burning questions about going on a sunset cruise in Key West, let’s talk about which cruise to choose!

Let me start by saying there are plenty of options, and one for every price point and style ! Below I will give a summary of 9 different cruise options, including the price, overall rating, what’s included, etc. This will help you choose the right one for you!

Note : Some of the cruises below link to Viator.com , which has some awesome benefits, including flexible cancellation policies and a “reserve now, pay later” feature! However, I do recommend checking the pricing of each cruise on the tour companys’ websites as well, in case they are running any promotions. Viator does have a Lowest Price Guarantee policy in case you do find something cheaper after you’ve already booked!

#1: Highest Rated Sunset Cruise : My Top Pick!

Sebago Watersports Sunset Sail

• Duration : 2 hours
• Rating : 4.5/5 stars⭐
• Includes : Open Bar, Live Music, Appetizers

If you search for Key West sunset cruises on TripAdvisor, this tour with Sebago Watersports is the most highly rated, with over 2000 reviews.

This is personally the company and tour we did on our last trip to Key West, and we had a fabulous time. The live music was fun, the food was delicious, and the drinks were flowing! I definitely recommend this cruise.

#2: Best Sunset Cruise with Full Buffet Dinner

Key West Sunset Dinner Cruise with Tropical Buffet Dinner Price : $93 Duration : 2 hours Rating : 4 stars If you’re looking for a sunset cruise that includes a full buffet dinner (instead of just apps), this cruise is your best option! In addition to unlimited well drinks, beer, and wine, it also includes a buffet dinner with a tropical twist.

The food includes fresh fish, Cuban bread, sweet plantains, and more! However, my personal opinion is you will find much better food on land, so this isn’t my first choice!

#3: Lowest Priced Key West Sunset Cruise

Key West Sunset Champagne Catamaran Cruise Price : $60 Duration : 1.5 hours Rating : 4.5 stars For those looking to save a little money, this Key West Sunset Champagne Cruise is the lowest of all the options, around $50 USD (when booked directly with Sebago ). This cruise is a little shorter than the others (1.5 hours instead of 2).

It also does not include hard liquor, just champagne, sangria, wine, and beer. However, it has great reviews and you can’t beat the price!

#4: Best Bang for Your Buck: Dolphins, snorkel & Sunset

Key West Dolphin Watching, Snorkel, and Sunset Cruise Price : $68 Duration : 3 hours Rating : 4.5 stars I highly recommend this combination dolphin watch sunset cruis e if you are looking to kill three birds with one stone: snorkeling, dolphin watching, and watching the sunset! This cruise is extremely well priced, as most snorkel trips are going to run you $50-$100 by themselves.

However, you won’t have a full half day in the water on this cruise (like other snorkel trips), since the entire cruise is 3 hours long.

#5: Best Luxury Key West Sunset Cruise

Wind and Wine Sunset Sail with Danger Charters Price : $109 Duration : 2 hours Rating : 5 stars Those looking for something more luxurious for their Key West sunset cruise need to check out Danger Charters. Their Wind and Wine sunset sail is the only sunset cruise in Key West that pairs wine (or beer) with gourmet cheese and meats (if you love charcuterie boards, this is the tour for you!).

It also takes place on an old schooner ship instead of a catamaran like most other sunset sails, which means less people!

Pssst: Planning a trip to Key West? Don’t miss my complete list of 25 epic things to do in Key West ! It includes activities like must-see Key West bars, restaurants, and attractions!

#6: Key West Sunset Cruise with Dance Floor

Fury’s Commotion on the Ocean Sunset Cruise Price : $88 Duration : 2 hours Rating : 4.5 stars What sets this Fury Water Adventures Sunset Cruise apart from the others is the large flat top dance floor at the front of the boat. The live music on the boat is normally a full band, and there is plenty of room for dancing!

This cruise also includes margaritas, champagne, beer, wine, plus some appetizers. A great option for those looking for a more party atmosphere. Fury is a common Key West water sports company, and they have many other tour options, like eco tours, jet ski tours, and Key West parasailing!

#7: Most Action Packed Key West Sunset Cruise

Fury’s Island Adventure and Sunset Combo Cruise Price : $158 Duration : 4.5 hours Rating : 4.5 stars Although this tour is a little pricer than the others, it is definitely the most action-packed! I will definitely be trying out this tour next time I visit Key West because it seems very off the beaten path. Included in the cost is a trip to a nearby sandbar where you can kayak and snorkel.

Then, you will head back towards Key West and admire the gorgeous sunset with a glass of champagne! Also included in the tour cost is snacks and lunch, plus beer and wine!

#8: Best Key West Private Charter Sunset Cruise

Sunset Sail Private Charter Cruise Price : $600 for 6 guests, $75 for each additional Duration : 2 hours Rating : 4.7 stars If you are traveling with a large group and want something more private, hiring a private sunset sail charter might be the way to go. If you have 12 people, the cost per person is surprisingly reasonable (around the same cost as the other public sunset sails in this guide!) Alcohol is not included, but you are welcome to bring your own!

#9: Key West Sunset Cruise on Glass Bottom Boat

Key West Glass-Bottom Boat Tour with Sunset Option Price : $70 Duration : 2 hours Rating : 4 stars For people with children, glass bottom boat tours can be a really fun excursion, especially if you don’t want to get in the water! This glass bottom boat sunset cruise will take you through North America’s only living coral barrier reef.

The guides will point out all the different sea creatures and marine life you may see: from fish to sharks to lobsters to turtles! As the sun sets, you’ll be given a glass of champagne to toast with!

Final Thoughts

That wraps up my guide to the best sunset cruises in Key West! Watching the sunset is the ultimate bucket list activity to do in Key West, and it’s even better when you do it on the ocean! You absolutely have to get out on the Key West water while visiting.

From booze cruises to luxury private charters, there is a sunset cruise for every type of traveler. I hope this guide gave you an overview of all the different types of sunset cruise options so you can pick the perfect one for you!

If you’re planning a trip to Key West, don’t forget to check out my 3 Day Key West Itinerary for even more information on visiting the Florida Keys!

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Sunset Cruises & Boat Tours

In key west, sunset cruises in key west.

Sunset Watersports is your one stop shop for Key West sunset celebrations. We have the island’s only sunset dinner cruise, an incredible sunset sailing experience or even an action packed sunset snorkeling trip.

Key West’s Best Sunset Sail:

Set sail and explore the beautiful waters of Key West! Enjoy a romantic sail with your loved one, experience the world-famous Key West sunset with a live tropical musician, open well bar & a great selection of appetizers.

Key West’s World Famous Sunset Dinner Cruise:

Climb about the world famous Party Cat catamaran for a night you won’t forget. Guests enjoy a delicious tropical food buffet made fresh in our on-board kitchen. Enjoy an unlimited open well bar & on of the island’s best live musicians as they set a true island vibe as you discover Key West’s legendary sunset.

Snorkel The Reef At Sunset:

Looking for a little more adventurous sunset experience? Look no further than this sunset snorkeling combo. We will take you to the best snorkeling location then open the bar and guests get unlimited draft beer & wine as we cruise around to enjoy the sunset cruise. Book your cruise online below ↓

Key West Sunset Dinner Cruise

• Clock 2 hours
• Users All Ages

Enjoy a beautiful Key West sunset with a tropical food buffet, live music, and an open well bar! Take in the unbeatable views as you groove into the sunset.

Kids go free!

Sunset Sip & Sail

Grab a tropical mixed drink and dance to a live performance while enjoying a legendary Key West sunset. Includes delicious appetizers!

Sunset Snorkel Combo

• Clock 5:00PM or 5:30PM
• Clock 3 hours

Join us for a beautiful late afternoon cruise out to the barrier reef for a refreshing dip in the crystal clear waters, then top it all off with a gorgeous sunset cruise through the harbor. This trip includes draft beer & wine.

Seasonal Cruises:

Fourth of july fireworks sail.

• Clock 1.25 hours

Celebrate the Fourth of July from the water! Grab a tropical mixed drink and dance to a live performance from one of Key West’s best entertainers while enjoying a legendary Key West sunset.

Key West & Stock Island Lighted Boat Parades

Join us for one of the most memorable nights on the water, Key West’s Lighted Boat Parade. This is your chance to ride in the parade. Includes draft beer, wine, champagne, appetizers & live DJ.

This was a great sunset cruise experience. The boat was clean and accommodating. The view of the Key West sunset was spectacular. The drinks were delicious and plentiful. I would highly recommend this trip!

It was so much fun!! Highly recommend doing this with your friends and family. We had a blast. Honestly well worth it. Jake even took photos for us and sent them to each group!

Our family had an amazing time on the sunset sip & sail and would definitely recommend Sunset Watersports to others. All staff were fun, informative, and my daughters had a great time. Overall, an amazing company to choose for some fun on the water!

The Budget Savvy Travelers

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Home » 10 Sunset Cruises in Key West – Which is Best for You?

10 Sunset Cruises in Key West – Which is Best for You?

Going on a sunset cruise in Key West is a must-do and is considered by many to be a rite of passage. After all, there’s probably no better place in the lower 48 to get out on the water and enjoy the golden hour than in the Conch Republic. However, not all cruises are the same, and some are definitely better than others—you don’t want to get stuck on an uncomfortable jam-packed boat with warm drinks, that doesn’t have anywhere to sit.

Key West is one of the most uniquely fascinating places to see in the country. With its laidback atmosphere and Caribbean vibes it’s the perfect place to escape the busyness of life for a while. However, if you’re looking to make your stay extra memorable then you should explore taking one of the 10 sunset cruises in Key West below.

Time to Relax

Use the chart below to assist in finding the perfect cruise.

Sure, you could save a few bucks and watch the sunset from Mallory Square , which is always a nice experience. Alternatively, you could sail past Mallory Square and Sunset Key and have an uninterrupted sunset experience out on the Florida Keys that you’ll remember forever.

10 Best Sunset Cruises in Key West

Below are the 10 best sunset cruises in Key West. Most cruises last about two hours and depart from either Opal Key Resort & Marina, Key West Bight Marina , or Garrison Bight Marina.

1. Snorkel and Sunset Sail

Jam to reggae beats and snorkel at North America’s only living coral reef, and enjoy a sunset sail tour. Unlimited rum punch, beer, wine, and sparking wine are provided, after snorkeling of course. At three hours long, this is the lengthiest tour on the list.

🥤🤿 Snorkel and Sunset Sail > Check Availability

2. Sushi Cruise

Sushi lovers will have a blast tasting fresh sushi while sipping on a refreshing drink as they watch the big orange ball sink into the Gulf of Mexico. This large pontoon-style boat provides a more intimate experience than some of the larger tour boats, which we like!

🍥⛴ Sushi Cruise > Check Availability

3. Cocktail Cruise With Open Bar

This cocktail cruise with an open bar is one of the most affordable ways to enjoy unlimited drinks on a sunset cruise in Key West. Visitors looking for a small group experience, a fun atmosphere, and comfortable seating are sure to enjoy the voyage! Light snacks including breads and spreads are also provided.

🍹🛥️ Cocktail Cruise With Open Bar > Check Availability

4. Classic Sunset Cruise With Live Music

When you think of a Key West sunset cruise this tour is most likely what you envision. This large catamaran has plenty of space to stretch your legs while you jam to live music. Moreover, with an open bar and a nice assortment of appetizers, this is the perfect tour for anyone looking to party!

🥳⛵ Classic Sunset Cruise With Live Music > Check Availability

5. Tiki Bar Tour

It doesn’t get more laidback than a Tiki Bar Tour in Key West. With only six passengers allowed, you won’t find a more intimate experience unless you charter a boat. Only water and ice are provided. However, passengers are allowed to bring their favorite adult beverages onto the boat. Check out these custom Key West koozies/party huggers to bring on board.

🗿⚓ Tiki Bar Tour > Check Availability

6. Premium Wine and Tapas

There’s no better sunset cruise in Key West for foodies and wine lovers than this one. Departing conveniently from Key West Bight Marina, the Premium Wine and Tapas Tour is 2.5 hours long and provides passengers with a plethora of scrumptious tapas and wine. Furthermore, the spacious and luxurious catamaran allows you to take in all of the sites and the sunset comfortably—also, the captain is obsessed with spotting dolphins!

🐬🍷 Premium Wine and Tapas > Check Availability

7. Pirate Cruise

Kids, and the kid in all of us, will feel like one of the Goonies aboard a vintage schooner—they even shoot a cannon! Water and snacks are provided, along with ice for anyone who would like to bring their own drinks.

🏴‍☠🦜 Pirate Cruise > Check Availability

Is it Your First Time in Florida? >   Read This

8. Schooner for Adults

Those passengers without kids, and looking to sail aboard a schooner will find this tour as a fantastic alternative to the one listed above (#7). Complimentary beer, wine, cocktails, and sangria are provided, along with some tasty appetizers.

⛵🍸 Schooner for Adults > Check Availability

9. Private Pontoon

Whether you’re celebrating a special event or you’re just looking for a bit of privacy, this private pontoon tour is the way to go if you’re on a tight budget. Your captain will guide you to all of the significant landmarks and get you in the best position to take in the sunset. Also, water and ice are provided—bring your own snacks and drinks to make it a party!

👨🏻‍✈️🚤 Private Pontoon > Check Availability

Looking to Rent a Boat For the Entire Day? > Check Out These Low Prices !

10. Private Classic Sailboat

If money is no object, this private classic sailboat tour is one of the best sunset cruises in Key West. Your group, of up to six people, can relax as your captain and their first mate navigate through the waters around Key West.

Of course, you’ll pass by all of the must-see landmarks, and the crew will spot marine life, and position the classic sailboat in the perfect spot for sunset. Finally, snacks and refreshments are provided, and of course, you can bring your favorite drinks along with you as well.

😎⛵ Private Classic Sailboat > Check Availability

There are dozens of sunset cruises in Key West but only the ones listed above are the best. Whether you’re looking to have a Goonies moment aboard a vintage schooner or nibble on sushi as you watch the sunset you can’t go wrong with any of the cruises listed above. Welcome aboard!

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Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

Get inspired with our most popular trips!

Private sunset sail.

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Sunset Sail on When & If

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Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

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Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

Three Classic Boats

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We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

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When And If is back at beautiful Stock Island Marina!

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• 305-294-5687

• SNORKELING TOURS
• COMBO TOURS
• SUNSET SAILS
• PARASAILING TOURS
• SCHOONERS SAILING TOURS
• PRIVATE CHARTERS

Discover the Best Key West Tours

Unforgettable trips like no other, experience the exceptional with sebago watersports, land’s end sunset sail.

Stunning sunset sail past Key West landmarks

Power Adventure

Includes all kinds of watersports

Key West Reef Snorkel - Afternoon

Experience Key West’s best afternoon snorkeling tour

Sunset Sail Tours

Parasailing tours.

Get the best aerial views of Key West with Sebago Watersports’ top-rated parasailing tours! Key West is the perfect place for new and experienced paragliders to (literally) be swept off their feet. Enjoy the Caribbean’s warm winds and crystal clear waters as you float serenely 300 feet in the sky.

Up for more air and water time? Upgrade to Sebago’s Power Adventure package, which combines parasailing and jet skiing into one awesome day on the ocean.

Starting at $69.95, Sebago’s tours depart multiple times a day. Pick the departure time that works best for you!

Snorkeling Tours

Schooner sailing tours, find your adventure, sunset sail, parasail tours, snorkel tours, all day power adventure.

Since 1988, Sebago Watersports has showcased the beauty of Key West to individuals, families, and business teams. The company that launched the iconic racing catamaran Sebago now offers some of the best tours in Key West, including snorkel adventures, kayaking excursions, parasailing, and sunset cruises.

As part of Red Hospitality & Leisure, the crew at Sebago Watersports crafts experiences that transcend the ordinary. Sebago Watersports’ long-standing operations in Key West mean that each guest explores its waters like a local; in fact, customers return so often because they feel like part of the Sebago ‘family.’ Join us and experience the difference for yourself.

Why Choose Us

Don't miss this world-famous catamaran excursion, featuring live entertainment, food made from scratch, and a full bar.

Experience secure parasailing with skilled guides and breathtaking views.

Limited capacity, authentic sailing, and vibrant marine life make our snorkel tours special.

From parasailing & Jet Skis to meals & cocktails, everything's included for a hassle-free, fun-filled day.

Private Charters

All of Sebago’s ships are available for private charters with each trip fully customized to your specifications, including beverages and food from Sebago’s own catering kitchen. We can arrange music for your special day – from a DJ, to a steel drum percussionist, to a 5 piece band. Or use the satellite radio on our catamarans.

Frequently Asked Questions

We do not have lockers or storage facilities in our office. Parties are welcome to bring a beach bag or backpack with personal belongings on our boats. However, if you have large luggage or suitcases these would be best stored at your hotel or vehicle.

Yes, all tours can be booked online. Please note that we require a minimum of 1 hour in advance to book tours online. Or you can contact our office directly to ask about short-term bookings.

No, we provide you with all you need, including sanitized snorkel, mask, fins and buoyancy compensator vest. If you already own snorkel equipment, you are welcome to bring it along and use it on the tour.

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Rated excellent by our visitors.

Announcing Sebago’s Brand-New Tours

• 786-526-0968
• [email protected]
• 205 Elizabeth Street. Key West, FL 33040

Private Charter Requests

Custom charter options.

• Experience amazing Key West Sunsets with customized catering options
• Morning or Afternoon Snorkels
• All day adventures or eco-tours
• Dolphin Watches
• Parasailing

CONTACT COURTNEY TO CUSTOMIZE YOUR VERY OWN WORRY-FREE DAY ON THE WATER.

Give Us A Call

• Phone: (786) 526-0487
• [email protected]

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Reader's Digest

Your Guide to a Florida Keys Road Trip: Key Largo to Key West

Posted: March 12, 2024 | Last updated: March 13, 2024

Your road trip guide to the Florida Keys

One of the best state road trips in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.

So if you're looking for the perfect Atlantic Coast road trip or cheap beach vacation , look no further than this road trip guide from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.

By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.

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Mile marker: 108–90

The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.

Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.

Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.

Best beach: Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.

Where to eat: Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best traditional restaurants in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.

Where to stay: If you can't get enough of the underwater world, stay at Jules' Undersea Lodge , the world's first underwater hotel. If you'd rather keep dry, try the adults-only Bungalows Key Largo .

Mile marker: 90–63

Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.

There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.

Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, go for a hike or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.

Best beach: Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.

Where to eat: For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.

Where to stay: When it's time to lay your head for the night, check in to one of the new oceanfront suites at Cheeca Lodge & Spa , or your own cottage at The Moorings Village & Spa .

Mile marker: 63–40

Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.

For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.

While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.

Best beach: Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the best beaches in Florida . And it's not just popular with humans; sea turtles nest here between April and October.

Where to eat: For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.

Where to stay: The Faro Blanco Resort & Yacht Club is set on the waterfront and gives you a taste of marina life. Lime Tree Bay Resort on Long Key has spacious townhomes for rent.

The Lower Keys

Mile marker: 40–4

After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an electric vehicle on this road trip so you don't disturb the animals.

Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.

Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.

Best beach: The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.

Where to eat: In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.

Where to stay: Consider the waterfront Sugarloaf Lodge , stay in an Airstream at Big Pine Key Resort  or pop a tent on one of the reserved campsites at Bahia Honda State Park.

Mile marker: 4–0

You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.

If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.

Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some hidden gems . The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.

Best beach: Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.

Where to eat: No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.

Where to stay: The boutique Gardens Hotel , the adults-only Kimpton Hotels Ridley House  or the new Capitana Key West , to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.

Art and history in the Florida Keys

Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for eco-travelers, but artists and history buffs too.

It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.

For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.

Planning your Florida Keys road trip

Now that you're inspired to hit the road, it's time to start planning. After budgeting for a road trip , your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.

If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.

If you're already driving one of the best road trip cars to get to Florida, you're all set. But if you need a loaner, choose one of the best cars to rent for a road trip . Consider packing these road trip essentials and download some of the best podcasts for road trips to make the miles fly by.

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