9 Sunset Cruises in Key West to Build a Day Around

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 into a Key West sunset aboard a spacious catamaran with live music, open bar, shrimp, hors d'oeuvres, and views of Mallory Square.

“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

Review of Key West’s two-hour sunset dinner cruise, with buffet, open bar, live music, sunset views, pricing, tips, and honest drawbacks.

“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 Small-Group Sunset Sail with Wine and Hors d’oeuvres

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

Sail Key West at sunset with up to eight wines, beer, soft drinks, and generous hors d'oeuvres aboard a small 26-person boat.

“Perfect end of the day watching the sunset and enjoying wine and snacks. Crew was amazing and boat was comfortable.”

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

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

Sail into a Key West sunset with live music, unlimited drinks, appetizers, and views of Mallory Square for a lively two-hour evening.

“This cruise was so much fun! The band was phenomenal! The crew worked non-stop serving drinks and making sure there was always plenty of appetizers available.”

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5.Sunset Sail in Key West with Beverages Included

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

Key West sunset sail review covering the small group, included drinks, crew, timing, value, weather policy, and what to expect aboard Floridays.

“This sailing was absolutely amazing!!! We sailed with about 20 people and it was wonderful!! The cruise was intimate yet engaging!!”

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

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

Sail Key West aboard America 2.0 with sunset views, open beer and wine, Champagne, and plated hors d'oeuvres for two hours.

“We went out on a cool day with a low cloud bank, so not a great sunset… but they can’t control the weather! The staff did a nice job keeping everything moving smoothly and distributing the hors d’oeuvres, which consisted of vegetable plate with wrench dip, shrimp with cocktail sauce, cheese, and crackers, and a brownie bite for dessert. They had a good offering of different wines and beers and sodas. Sadly, we did not see any wildlife to speak of except birds. It was fun to visit with the people around us, of which there were a lot! It was impressive to see the crew of Milo, Mary, Dan…”

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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

Key West sunset sail with wild dolphin spotting, wine, champagne, beer, shrimp cocktail, tapas, and views of Mallory Square.

“The sunset cruise was a lot of fun. We enjoyed the views, the beautiful sunsets, and the dolphins. The appetizers were delicious and the staff were knowledgeable and fun!”

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8.Key West Champagne Sunset Catamaran Cruise

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

See Key West’s famous sunset from a spacious catamaran with champagne, beer, wine, sangria, island views, and a friendly crew.

“The boat crew was friendly the music was good very nice thank you for a wonderful time the food was great I would not expect any thing less”

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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, snorkeling, and sunset cruise, with practical advice on wildlife sightings, reef quality, crew, and value.

“If there is one activity not to be missed in Key West, it is this one !! thank you very much it was magic”

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