The 9 Sailing Trips with an Open Bar in Key West That Earn Their Price

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

Sail from Key West for about two hours aboard a spacious catamaran with sunset views, live local music, an open bar, shrimp, antipasti, mini tarts, and soft drinks. Arrive 30 minutes early, claim a good bow seat, and bring a sweater for breezy evenings.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

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2.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

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

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef. You’ll get gear, a safety briefing, and time to snorkel before the open bar begins on the ride home. Captain Brett and the Sebago crew are known for a safety-first approach, though the boat can feel busy.

“The boat, the trip and the crew were all amazing. Recommend this highly. Will definitely go on this excursion with the same company again!”

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3.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Board Fury’s 65-foot catamaran at Greene and Elizabeth Streets for two hours of live cover music, unlimited margaritas, beer, wine, Champagne, and seasonal appetizers. Sail past Mallory Square and possibly Fort Zachary Taylor while the crew picks the best route for sunset. Arrive early for seating.

“Not your usual review as our sunset cruise was cancelled by a freak raging windstorm. Just wanted to thank the team there at the pier that handled everything so professionally and quick. Rescheduling was offered but we had opt for cancellation as it was our last night in town.”

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4.Key West Champagne Sunset Catamaran Cruise

★★★★★★★★★★4.5 · 586 reviews · 1 hour 30 minutes (approx.) · from $59

Sail from Key West’s Historic Harbor for about 90 minutes aboard a spacious catamaran. Enjoy included champagne, wine, beer, sangria, soft drinks, and water while the captain points out sunset views, marine life, Mallory Square, and Fort Zachary Taylor. Bring a light jacket, camera, and photo ID if you drink.

“activity for a mid-sized bachelorette party: captain and crew were awesome, boat was gorgeous, bottomless cocktails, and the perfect length of time on board. event was a hit for the group and the peak of the trip!”

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5.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 Captain Janet or another experienced captain. Enjoy drinks, a personal plate of hors d’oeuvres, open-water views, and possible sightings of dolphins, turtles, and the Green Flash.

“everything the captain and crew the boat is beautiful the food and drinks are great and the scenery beautiful well worth every penny 😀”

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6.Sunset Sailing Trip with Open Bar, Food and Music

★★★★★★★★★★4.5 · 310 reviews · from $80

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat. You get two hours of open-bar drinks, light appetizers, live music, and a clear sunset view offshore. The crew may let you help raise the sails or pose at the wheel. Bring your driver’s license.

“Beautiful cruise and an amazing sunset. We enjoyed the food, drinks and music”

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7.Sunset Sail with Live Band, Drinks, and Appetizers

★★★★★★★★★★4.7 · 171 reviews · 2 hours - 150 minutes · from $79

Board Fury’s 65-foot Commotion on the Ocean for about two hours of sunset views, live local music, open beer, wine, champagne, margaritas, and light appetizers. Choose the sundeck or shaded lounge, but plan ahead if you get seasick or need dietary accommodations.

“Staff was not only friendly they were safety conscious The band was very good the busy was clean. Food was good. This was our second time on this cruise. Would def recommend”

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8.Windjammer Champagne Sunset Sail

★★★★★★★★★★5.0 · 18 reviews · 2 hours · from $89Top rated

Spend two hours aboard the two-masted Appledore II, helping raise the sails before cruising past Key West landmarks and settling in for sunset. Champagne, wine, sangria, beer, spirits, soft drinks, and water are included. Captain Pedro and the English-speaking crew add sailing tips and local context.

“Beautiful sunset sail. The crew were extremely friendly and shared tons of information about the ship and gave us an unforgettable experience!”

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9.Catamaran Snorkel with Seafood Boil and Open Bar

★★★★★★★★★★4.4 · 9 reviews · 4 hours · from $89

Spend four hours aboard a spacious Sebago catamaran, snorkeling at two Key West sites such as Sand Key, then eating shrimp, corn, and potatoes from a Low Country boil. English-speaking instructors help all skill levels, and the premium open bar keeps the post-snorkel hours easy.

“Superbe activité. Équipage très sympathique et agréable. La nourriture était très bonne et boissons à volonté idéal pour se rafraîchir après les plongée magnifiques on a pu faire du snorkeling et voir de très jolis poissons.”

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