Top 8 Key West Boat Tours

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Spend about two hours aboard Sebago’s large Key West catamaran, sailing past Mallory Square, Fort Zachary Taylor, and Sunset Key. Your ticket includes an open liquor bar, champagne, wine, sangria, premium beer, soft drinks, chef-selected hors d’oeuvres, and live music from local performers. Arrive early for a good bow seat, and bring a sweater for cool or windy evenings.

“Fun crew and drinks were plenty. There is enough room for everyone and the boat was well handled. Highly recommend this one.”

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

★★★★★★★★★★4.5 · 1,707 reviews · 2 hours (approx.) · from $92

Board a 65-foot yacht at Key West’s historic seaport for a two-hour evening cruise. Enjoy crew-served Caribbean buffet dishes, unlimited well drinks, beer, wine, and soft drinks, then head upstairs for sunset views, live music, and a passing look at Mallory Square.

“Excellent crew and spacious room for dining. Great open air top level gives great views and picture opportunities”

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3.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59Best value

Join Sebago Key West aboard the 69-foot catamaran Marquesa for a roughly three-hour afternoon sail from the historic seaport. After the hour-long ride to the Florida Reef, the crew provides gear, safety guidance, and time to snorkel among coral and tropical fish. Once you are back aboard, enjoy unlimited beer, wine, cocktails, and soft drinks on the return sail.

“The weather was perfect on our snorkeling day trip to the reefs. The boat ride was about an hour to get 8 miles offshore. The catamaran was smaller than usual and it was crowded but we still fit and had fun. We couldn't drink until after snorkeling and returning back to the docks. Safety precautions were paramount and the captain and crew instructed everyone on the proper way to snorkel. I saw the reefs and took video down below. A nurse shark crossed my path which wasn't too bothered by us humans but it was incredible experience. I'm an expert snorkeler and diver but this was fun. Good selection of…”

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4.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125Top rated

Sail from 255 Front Street for about two hours with a maximum of 26 people. The crew pours up to eight wines, offers beer and soft drinks, and serves small plates such as cheese, fruit, and skewers while you watch the Key West sunset. Crews may include Mary, James, Connor, Molly, or Tony.

“Our sunset sail was perfect from start to finish. We absolutely loved the wine tasting and appetizers — you never know what you’re going to get on these types of excursions, and sometimes you brace yourself for cheap wine and sad snacks… but this was the total opposite. The wines were genuinely great bottles, and the cheese apps were delicious and beautifully done. We also adored our all-women crew. They were fun, warm, and made the whole experience feel extra special — the perfect vibe for a girls trip celebrating our 40ths. Would 100% recommend this sail to anyone looking for something elevated, relaxing, and unforgettable.”

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5.Dolphin Watching and Snorkeling Eco Cruise Tour

★★★★★★★★★★4.6 · 757 reviews · 3 hours · from $79

Spend three hours on a 45-foot power catamaran from Key West, watching bottlenose dolphins and snorkeling in the Key West Wildlife Refuge. English-speaking guides such as Liv, Lisa, Ally, and Nicole have led trips, with gear, water, sodas, and drinks included. Choose a late departure seasonally for sunset views.

“providing proper snorkeling gear could help the non swimmers”

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6.Dolphin Watching and Snorkeling Sunset Cruise

★★★★★★★★★★4.4 · 493 reviews · 3 hours · from $79

Spend three hours aboard Sunset One searching for wild dolphins, snorkeling near Cottrell Key in the Key West National Wildlife Refuge, and watching sunset from the water. Guides such as Kevin, Kylie, Madison, John, and Sparkles have led past trips, with English commentary, safety gear, snorkel equipment, and draft beer included.

“Amazing trip! We saw 3 groups of dolphins swimming nearby and even under the boat, so the trip already made us happy. After that we snorkeled for about 45 minutes which was absolutely fantastic and made a lot of fun. The way back home while watching the sunset was a nice addition to the fantastic trip. Would definitely recommend, although it’s not guaranteed to see dolphins.”

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7.Key West Signature Sunset Cruise with Open Bar, Food & Music

★★★★★★★★★★4.5 · 418 reviews · 2 hours · from $79

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat for a two-hour sunset cruise. You’ll get open-bar drinks, light appetizers, live music, and room to move between decks. The crew may invite you to help raise the sails or pose at the helm. Bring your driver’s license.

“Really nice and friendly team! No real sailing but a very chilled little trip south of Key West!”

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8.Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Board the America 2.0 behind Schooner Wharf Bar for a two-hour sunset sail with complimentary drinks and a personal hors d’oeuvres plate. You’ll pass Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier while the crew handles the sails. Captains including Janet and Amber have led highly praised departures.

“This was a wonderful experience with an excellent crew.”

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