Best Open Bar Experiences in Key West: Our Top 7

1.Key West Afternoon Reef Snorkeling with Open Bar

★★★★★★★★★★4.5 · 419 reviews · 3 hours (approx.) · from $59Our pick

Board the Sandie Cat at 201 William Street for a guided afternoon snorkel on Key West’s coral reef. The crew provides equipment and instruction, then serves unlimited beer, wine, champagne, rum runners, margaritas, and mixed drinks after you leave the water. Expect about an hour of cruising each way.

“Captain and crew were friendly, ride out and in were both nice and smooth. Beautiful day on the water. Not much to see besides fish and coral but worth it to spend the day on the water with family and a good time”

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2.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 get unlimited basic drinks, light appetizers, live music, and room to move around. The crew may invite you to help raise the sails or take a turn at the wheel.

“What a blast!!!!!! So beautiful, great music, great staff, and an all around amazing time! Definitely recommend for a true key west experience!”

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3.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, panoramic water views, unlimited well drinks, beer, wine, champagne, and light appetizers. Captain Anna has earned praise for her calm, friendly presence. Children may join, so expect a mixed crowd rather than an adults-only party.

“This sunset cruise was the best. Fabulous crew and the boat was gorgeous. Great time and great sunset”

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4.Afternoon Reef Snorkel Tour with Open Bar

★★★★★★★★★★4.3 · 268 reviews · 3 hours · from $59

Spend three hours aboard a Sebago catamaran, with instruction, reef snorkeling, and a return sail with cocktails, beer, wine, and soda. The captain chooses the site based on wind and water conditions, while the crew helps first-time snorkelers get comfortable.

“Amazing experience snorkeling with the Sebago team. Beautiful reef with multiple fishes, a shark and even a sea turtle. A light delicious lunch and drinks appreciated on top of that.”

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5.Sunset Dinner Cruise with Open Bar & Live Music

★★★★★★★★★★4.5 · 228 reviews · 2 hours · from $92

Spend two hours aboard The Party Cat on a Key West harbor cruise with a tropical buffet, open bar, and live music on the upper deck. You will see the sunset over the Gulf of Mexico, hear performers such as Dante, and enjoy a lively evening near 201 William Street.

“Fantastic entertainment! Well organized. Good food and great drinks. Would definitely do it again!”

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

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

Sail from Key West Historic Seaport aboard a classic schooner for two relaxed hours. Captain Joe, Josh, and crew members such as Cristina, Michael, and Vitali have helped make this a polished small-group outing, with cocktails, wine, beer, champagne, snacks, and wide sunset views.

“It was everything I expected and more. This was my first sunset experience on a schooner and well worth it. Captain Joe and 1st Mate, Michael were great! It was cool to see them open the sails. They were both so attentive to everyone’s needs. The cocktails and appetizers were great. It’s a FULL bar just as advertised. Captain Joe took the boat where there wasn’t another boat between you and the perfect sunset where we were fortunate enough to see the green flash off the water at the sun disappeared. I will take this sunset experience again the next time I’m in town. By far the best sunset cruise…”

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7.Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

★★★★★★★★★★5.0 · 169 reviews · 2 hours (approx.) · from $65

Set out from 711 Eisenhower Drive for about two hours with Captain Steve, Scott, Zac, or another local captain at the helm. Your open bar includes beer, wine, soft drinks, and cocktails, while the crew handles photos, music, and commentary. The boat holds up to 35 people, though many sailings are much smaller.

“The captain and the bartender were excellent! Great job! Made trip very safe and enjoyable! Thanks! They were both very knowledgeable and shared much local information.”

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