Top Key West Cruises &amp; Sailing

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

Key West Sunset Sail with Live Music, Drinks and Appetizers

Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The sun is shining bright, and the air is filled with the scent of salt and sunshine. As you approach the sandbar, the boat glides over shallow waters, revealing stretches of soft, white sand inviting you to explore. Once you anchor, the fun begins! You can jump off the boat and wade into the warm, shallow waters, where the gentle waves lap at your feet. The atmosphere is relaxed, with laughter and conversation floating through the air. Some folks might set up beach games, while others enjoy swimming or soaking in the sun. Time seems to slow down as you enjoy this little slice of paradise, surrounded by friends or newfound acquaintances. Whether you’re collecting seashells, taking a dip, or simply lounging in the sun, a sandbar trip on a tiki boat is a perfect blend of relaxation and adventure.

Key West Sandbar Safari on One of a Kind Tiki Boat

3 hours 30 minutesFree Cancellation

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sail in Key West with Beverages Included

1 hour 30 minutesFree Cancellation

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

Shark and Wildlife Viewing Adventure in Key West

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

2 hours 30 minutesFree Cancellation

Watch the sun set over Key West from the deck of a traditional schooner on an evening sailing experience with a full open bar. Settle into the rhythm of the water as the crew sails offshore, taking in unobstructed Gulf views while bartenders serve cocktails, wine, and spirits throughout the cruise. Combining classic sailing with an easygoing onboard atmosphere, this is a memorable way to experience Key West at sunset.

Classic Key West Schooner Sunset Sail with Full Open Bar

Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters

4 hoursFree Cancellation

Key West's Favorite Afternoon Dolphin Sail

2 hours 30 minutesFree Cancellation

Key West Glass-Bottom Boat Tour with Sunset Option

1 hour 45 minutes to 2 hoursFree Cancellation

Key West's Island Adventure Sandbar Tour with Kayaking

3 hours 30 minutesFree Cancellation

Get ready for fun in the sun—and check off two top experiences in just one trip—on this dolphin-watching and snorkeling tour off the coast of Key West. Departing Key West, look out for dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breezes, and select from a variety of refreshing beverages on board the boat.

Key West Dolphin Watch and Snorkel Tour - Eco Adventure

Set sail from Key West aboard a spacious catamaran for a morning snorkeling cruise combining relaxation and adventure. Glide across the waters where the Gulf of Mexico meets the Atlantic Ocean before stopping at a secluded snorkeling location. Enjoy a gourmet breakfast and unlimited mimosas on board, offering a convenient way to experience Florida’s coastal scenery before the rest of your day begins.

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

Not only is Key West a playground paradise for adults, it is for dolphins, too. See how many of these playful creatures you can spot on this small-group sailing tour. You’ll board Our SQUID, we designed and built SQUID from scratch to ensure our guests, and the animals, have the best wildlife experience possible. This catamaran will take you and a crew trained by biologists into the waters around Key West. After watching dolphins swim, you’ll jump into the water and snorkel around the coral reefs to view other marine life.

Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

4 hoursFree Cancellation

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

Schooner Appledore Day Sail with Full Bar in Key West

Sail to a gorgeous snorkeling spot off the coast of Key West to explore a coral reef home to rainbow-colored fish, anemones, eels, and more. On the hour-long sailing trip to the reef, sip included wine, beer, or soft drinks while watching for dolphins and sea turtles. The captain chooses the snorkeling spot according to each day’s conditions, ensuring the best experience for your group.

Key West Sailing & Snorkeling: A Reef Adventure

Key West Afternoon Reef Snorkeling with Open Bar

Key West Sunset Sail Aboard Legendary Schooner Appledore

Get ready to spend a half-day soaking up the sun and enjoying Key West’s diverse ecology during this fun sandbar and mangrove tour. Discover the backcountry waters and secluded sandbars around the busy island, all while sipping on cold drinks. This guided kayak ecotour takes you into the mangrove isles to spot dazzling marine life before heading to a sandy beach to knock back a few alcoholic or nonalcoholic beverages.

Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

5 hoursFree Cancellation

Key West Champagne Sunset Catamaran Cruise

1 hour 30 minutesFree Cancellation

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Must-Dos in Key West

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What are people saying about Key West

Key West Sandbar Safari on One of a Kind Tiki Boat

Christopher_H, Sep 2026

Must do Key West excursion

Dawson and Captain Brett were amazing. Definitely a must do excursion. Approximately a 40 minute boat ride to the sandbar. Sandbar was clean and perfect. Drinks steady flowing. About an hour and 45 minutes at the bar meeting and mingling with other parties on board. Must do. Thanks Brett and Dawson. Very fun, professional and safe.

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

David_F, Sep 2026

Key West Sunset

Great time with Captain Sandy. Nice selection of wine and cheese after a champagne toast to start the cruise. A little over 2 hours on the water. Sails came up and nothing but relaxed music a a gorgeous sunset that seemed to last forever small group is the way to go especially in off season. We have hundreds of sunset pictures but we added a couple more last night

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

linda_k, Aug 2026

Super Experience for all ages

We had an awesome time on this excursion. There were 21 of us total which is a LOT. Ages ranging from 2 years old to 65 years old. The crew was super helpful and the water was beautiful. The only odd thing is the captain approached our group a number of times telling us we needed to tip the crew because we were such a large group. We ALWAYS tip the crew and certainly do not need numerous reminders. It was uncomfortable how pushy he was. We tipped over $300 as a group so the crew was well taken care of. It was just odd.

Key West Sailing & Snorkeling: A Reef Adventure

Richie_C, Aug 2026

Great time

We had such a lovely time and got to see more fish than I expected. The staff were very friendly and so nice! If you get sea sick/ motion sickness I would definitely recommend taking medicine before going as the sea was a little rough and it's about an hour commute from the dock to the reef.

Classic Key West Schooner Sunset Sail with Full Open Bar

Kathy_F, Aug 2026

Highly recommend Appledore Schooner

Great experience for our Anniversary! Spectacular views on the Appledore Schooner . Not only are the sunsets gorgeous, you also sail around Sunset Key and see Key West from a different view. FUN Joe & Christina are very experienced sailors with a great sense of humor and making sure everyone had a fantastic time. I loved the small group of 14. The drinks were flowing and our appetizer was shrimp, fish dip with crackers. Not a lot of food but really we were enjoying the Schooner experience! It was windy in some areas and the boat was tilting. My husband gets sea sick but this did NOT faze him one bit. Another fun moment that the other boats can’t do is have a “duel” with another Schooner and “fire the cannon” at each other and also all the people lined up at Mallory Square! Yes, there is a bathroom !

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

Kristen_A, Jul 2026

Best. Crew. Ever.

Best. Crew. Ever. Logan, Bracken and Nic were fantastic! I appreciated their welcoming spirit, well also ensuring the upmost of safety. Double and triple checking accounts to ensure we were all on board and accounted for. Great personalities and the boat was incredibly clean. The sunset was absolutely gorgeous and could not have asked for better weather. We even got the moonrise the night leading into a full moon. I call it great luck!!! Definite one to do!!!

Key West Reef Snorkel & Sail Adventure

Michelle_B, Jul 2026

We had an amazing time on...

We had an amazing time on this snorkeling experience! It was both of our first times snorkeling, and the crew made us feel comfortable from the start. The marine life was absolutely incredible—we saw so many beautiful fish and underwater scenery that exceeded our expectations. It was such a memorable experience, and we’d definitely recommend it to anyone visiting! 🐠🌊

Key West's Island Adventure Sandbar Tour with Kayaking

Amy_G, Jun 2026

Best day ever!

A true Key West Island experience! A must do for any nature and water lover. It was like having a private island all to ourselves. Went kayaking near the mangroves, and went swimming in the warmest most beautiful water. Food, cocktails, and music were an added bonus. Captain Jude and Mate Allie took great care of us. We loved it so much we’re going back tomorrow!

Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure

Laura_S, Apr 2026

Beautiful sunset, no crowds.

A great smooth ride and not crowded like other tours. Madison was wonderful and gave us lots of interesting information about the keys. Only thing I would do is make the barstools more comfortable. They are really high and your legs hang, I’m 5’8. They need to add a foot rest on the tiki bar itself or on each stool. Other than that I would highly recommend.

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Alex_W, Apr 2026

Make sure you go to the...

Make sure you go to the green awning on the left when you arrive. We got caught up in the wrong line to the right and almost missed the cruise. Aside from the arrival confusion all else was truly exceptional. Great crew, beautiful, clean, and comfortable ship, a truly relaxing and enjoyable excursion.

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

Lora_B, Feb 2026

Amazing crew, amazing sunset!

The boat was freshly cleaned and well-stocked. Our captain Steve was friendly and had a bunch of interesting information about the island. He played great music and was always up for suggestions. We had an intimate party of great guests. Sky, the bartender made excellent drinks and had great suggestions. They had about 9 different beers available and a full liquor bar, as well as wine. Both Sky and Steve went out of their way to make sure we were having a great time and had a beautiful view of a beautiful sunset on the water, we even got to see a couple pods of dolphins that they tracked down for a closer view. We enjoyed our experience so much, but what really made it special was the hospitality of Sky and Steve. They made the trip extraordinary, even pointing out different beaches and houses along the way to our sunset view and back. Overall, the trip was about 2.5 hours or so and we will definitely be back the next time we are in Key West to jump aboard “The Good Times”! If you booked through Viator, the details were limited but this is run through Snuba of Key West with a departure time of 5/515pm.