Top 13 Sunset Cruises in Key West

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

Review of Key West’s sunset catamaran sail with an open bar, live music, shrimp, hors d’oeuvres, and views from Mallory Square to Sunset Key.

“The captain and crew were extremely attentive to all of the passengers. They even brought drinks and horsdoeuvres to the passengers hanging out on the main deck who were watching the Amazing sunset. They even mingled with the everyone and helped take pictures when asked. This was a highlight of our time at Key West!!”

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

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

Key West sunset dinner cruise review with buffet, open bar, live music, yacht views, practical tips, crowd notes, and value advice.

“Great way to add an experience to your 50th Anniversary. Good food and drinks! And the crew was excellent!!”

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

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

Review of Key West’s small-group sunset sail with up to eight wines, beer, hors d’oeuvres, friendly crew, and practical booking tips.

“Just do it! The crew is wonderful. The wine & appetizers were delicious. It was a chilly and windy sail, but the crew had blankets ready and it was picture perfect. And, a couple got MARRIED during the sail!”

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

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

Review of Key West’s two-hour sunset sail with live music, unlimited drinks, appetizers, sunset views, practical tips, and honest value advice.

“Beautiful,senic,fruendly,best sun set ever. We enjoyed the trip with wonderful music and fabulous service.”

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5.Sunset Sail in Key West with Beverages Included

★★★★★★★★★★5.0 · 907 reviews · 1 hour 30 minutes (approx.) · from $79

Review of Floridays’ Key West sunset sail, with drinks, small groups, harbor views, practical tips, value, and cancellation details.

“It was absolutely wonderful! The crew was amazing, the boat was beautiful and the views were incredible!”

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6.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122

Review of Key West’s America 2.0 sunset sail, with sailing views, open beer and wine, plated hors d’oeuvres, tips, and honest value advice.

“Sunset was enchanting and the crew was super accommodating! Captain Dan also added historical tid bits that enhanced the Key west experience. Great trip!”

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

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Review of Key West’s sunset catamaran sail with wild dolphins, wine, champagne, shrimp cocktail, tapas, and landmark views.

“Very good value,unlimited drinks lots of dolphin sightings and very helpful staff and perfect length of trip”

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8.Key West Champagne Sunset Catamaran Cruise

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

Sail from Key West for 90 minutes of sunset views, included champagne, wine, beer, sangria, soft drinks, and friendly crew service.

“We had a great time. Our crew was fantastic. If you have a chance to do this it’s worth it !! Carly and John were fun to be with. Thx”

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9.Dolphin Watching and Snorkeling Sunset Cruise

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

Review of Key West’s 3-hour dolphin and snorkeling sunset cruise, including wildlife, reef conditions, crew, value, practical tips, and who should book.

“Amazing trip. Weather was perfect. Saw plenty of dolphins. Captain John, Katie and Stephanie were superb and made the trip. Great safety briefing, boat was spotless, equipment (snorkel, goggles etc) was in great condition. Lovely music, cool vibe and the sunset was just incredible: Thank you🌅”

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

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

Review of Key West’s 2-hour sunset catamaran cruise with open bar, appetizers, live music, dancing, and sunset views for $79.

“Sunset cruise-great music. Wonderful staff. Food and appetizers could have been a little better but open bar. People really enjoyed themselves.”

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

★★★★★★★★★★4.5 · 370 reviews · 3 hours (approx.) · from $59

Review of Key West’s Rum and Reggae tour, with reef snorkeling, sunset views, onboard drinks, practical tips, and honest value advice.

“Saw many fish, small but beautiful! A group of over 50 fish right in front of me, they were not scared at all. A very exciting experience. Will come back to do it again, but probably not in January again. The water was not cold but it was cold after coming out of water.”

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12.Schooner Sunset Sail with Food & Drinks

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

Sail aboard the America 2.0 for a two-hour Key West sunset with open drinks, hors d'oeuvres, wildlife views, and a chance at the Green Flash.

“Such a beautiful sunset cruise! The crew was incredibly friendly and knowledgeable, which made the whole experience even better. The sail was the perfect length — long enough to truly enjoy being out on the water, but not so long that you felt restless. They served appetizers throughout the trip, and everything was delicious while still light — just right for a relaxing evening on the boat. 🌅⛵️”

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

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

Review of Key West’s two-hour sunset catamaran sail with live music, open bar, appetizers, practical tips, value, and honest drawbacks.

“We really enjoyed being on the water during sunset. The boat had plenty of seating for all the guests and plenty of room to move around to the best areas for views. The live violin duet was a great accompiment to the views. The free pinot grigio and food were what would be expected on this type of tour, acceptable. Great value for the price.”

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