14 Sailing Tours with an Open Bar in Key West for the Logbook

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 an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and hors d’oeuvres. Local musicians provide live music as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Arrive 30 minutes early and bring a sweater for cool or windy 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, about 7.5 miles offshore. The crew supplies masks, fins, instruction, and safety guidance. Expect roughly 45 to 60 minutes in the water, then beer, wine, soft drinks, and cocktails on the ride home. Captain Brett has led some departures.

“The crew is great! They explained how to use the equipment and worked to make the experience a great one!”

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

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

Spend about two hours aboard Fury’s 65-foot catamaran, with live local musicians, unlimited margaritas, champagne, beer, wine, soda, and seasonal appetizers. You can dance, sit on the sundeck, or watch the sunset from shaded decks. The cruise returns to Greene Street in time for dinner.

“Sunset was amazing. Staff were great and very engaging. Service was great. Lots to eat & drink. It was a beautiful night.”

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4.Schooner Sunset Sail with Food & Drinks

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

Sail for two hours aboard the America 2.0, a polished wooden schooner with teak decks and 3,600 square feet of canvas. Enjoy drinks and a personal hors d’oeuvres plate while the crew sails past Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Captain Janet is a favorite on many departures.

“Friendly staff, clean boat, and overall great experience. Would recommend to anyone in the Key West area!”

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

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72

Board the Sandie Cat at 201 William Street for a two-hour Key West sunset sail with live music, unlimited well drinks, beer, wine, champagne, and light appetizers. The three-deck catamaran offers broad sunset views, though the food is snack-sized and the mood can range from calm to lively. Captain Anna has earned praise for her friendly, confident handling of the boat.

“Great drinks and fun crew! We had a great time on the boat and enjoyed the music and the other guests.”

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

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

Set sail from Key West’s historic seaport aboard the three-deck Sandie Cat. You’ll get two hours of sunset views, unlimited basic drinks, light appetizers, and live music, with time to dance or help raise the sails. Captain Matthew and the crew may even let you take a turn at the wheel for a photo.

“This cruise was over the top. The food the drinks the entertainment and the sunset a very memorable trip!”

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7.Classic Key West Schooner Sunset Sail with Full Open Bar

★★★★★★★★★★5.0 · 213 reviews · 2 hours (approx.) Top rated

Sail from Key West’s Historic Seaport aboard a classic schooner for about two hours, with a maximum of 22 people. Captain Joe, Josh, and crew members such as Christina, Michael, Molly, and Vitali have hosted recent trips. Expect cocktails, wine, beer, champagne, soft drinks, water, hors d’oeuvres, and sunset views, with no shore stops.

“We had a great time on the Schooner Sunset Cruise. The three young gentlemen running the show did a phenomenal job on all fronts. I highly recommend this excursion. We will definitely be making this a tradition! Thank you for the memories!!”

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8.Key West Day Sail on Schooner America 2.0 with 2 Drinks

★★★★★★★★★★5.0 · 198 reviews · 1 hour 30 minutes (approx.) · from $73

Board the detailed America 2.0 replica in Key West for a 90-minute coastal sail past Mallory Square, Fort Zachary Taylor, Sunset Pier, and Sand Key Light Tower. The crew handles the sails while you watch for dolphins, sea turtles, and waterbirds. Two alcoholic drinks, soda, and water are included, with extra drinks available by card.

“It was really fun, relaxing and the crew was the best. My wife is handicapped and they were helpful with questions.”

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

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

You’ll spend about two hours aboard Fury’s 65-foot Commotion on the Ocean, cruising off Key West as local musicians play. Beer, wine, champagne, margaritas, sodas, lemonade, water, and seasonal appetizers are included. Choose the shaded lounge or open sundeck, and book July 4 for sunset views plus fireworks.

“Nice drinks and great music, just good could be better! Leeet‘s rock 🤟”

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10.Windjammer Champagne Sunset Sail

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

Spend two hours aboard the wooden schooner Appledore II, helping raise the sails before cruising past Key West landmarks. Your drink choices include champagne, wine, sangria, beer, liquor, soft drinks, and water. Captain Pedro has shared sailing tips and local information on past trips, making this a relaxed sunset outing with a hands-on touch.

“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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11.Champagne Dolphin Sail and Reef Snorkel

★★★★★★★★★★5.0 · 5 reviews · 3 hours (approx.) · from $108

Set out from Key West with captains Bailey and Micah aboard Catamaran Echo, conditions permitting. You will cruise through local dolphin waters, watch for dolphins and calves, then spend about an hour snorkeling at the coral reef with sanitized gear and simple instruction. Champagne and other adult drinks are served during the roughly three-hour trip.

“we had a truly fantastic time. our captains/guides were Bailey and Micah who facilitated a lovely experience, the views were top notch, and the provisions were plenty. we will be return customers for similar excursions when we return to Key West. thanks for a great day!”

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12.Catamaran Champagne Sunset Sail

★★★★★★★★★★4.7 · 3 reviews · 1h 30m · from $79

Leave Key West’s Historic Seaport aboard Sebago’s Marquesa, a luxury catamaran with raised sails, open-water views, and unlimited champagne, wine, beer, sangria, soft drinks, and water. Your English-speaking captain points out Mallory Square, Sunset Key, and Fort Zachary Taylor before positioning the boat for sunset.

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13.Key West’s Schooner Appledore Star Champagne Sunset Sail

★★★★★★★★★★5.0 · 3 reviews · 2 hours · from $109

Spend two hours aboard the Appledore Star, Key West’s only bugeye schooner, as the crew raises sail and guides you past Mallory Square, Navy Mole, and Fort Zachary Taylor. Sip champagne, wine, sangria, beer, or a top-shelf cocktail while enjoying chef-prepared hors d’oeuvres and a classic Gulf sunset.

“Petit groupe, équipage au top, très belle autre façon de vivre the sunset à KW”

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14.Schooner Full Moon Night Sail with Drinks

★★★★★★★★★★5.0 · 2 reviews · 1h 30m · from $83

Spend 90 minutes sailing Key West at night aboard the teak-trimmed Schooner America 2.0. You’ll watch the shoreline lights, stargaze beneath the full moon, and enjoy two alcoholic drinks if you’re 21 or older, plus soda and water.

“Fabulous experience! This was our first time sailing. 100% recommend!!!”

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