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

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

Key West small-group sunset sail with wine tasting, beer, and hors d’oeuvres on a schooner-like boat for about two hours.

“Go on the sunset sail! You won’t regret it! Our friend group of 6 went on a sunset sail with captain Mary, Lexi, and Connor. It was the highlight of everyone’s Key West trip! The crew was amazing. You could tell that they absolutely love what they do and truly care about their passengers experience. I’m sure that they could cater to any age group and make any sailing experience worthwhile. We loved the way that they served wine and appetizer courses. The appetizers were creatively served skewer style, but still kept taste in mind by pairing things such as fig and cheese, mozzarella and tomato, as well as apples…”

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2.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 dolphin watching plus premium wine and chef’s tapas. Small group, landmark views, and an easy 2.5-hour plan.

“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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3.Key West Champagne Sunset Catamaran Cruise

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

A 69-foot Key West catamaran at sunset with captain-led views, included champagne-style drinks, and a laid-back 1.5-hour sail from the harbor.

“You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to the 2 hour sail with live music and hors d’oeuvres. The crew was amazing and on point attending to any needs we had. Highly recommend this cruise.”

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4.Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

★★★★★★★★★★4.5 · 146 reviews · 3 hours (approx.) · from $69

Two reef snorkel stops plus a Key West sunset sail with beer and wine on a fast catamaran, for about 3 hours.

“Great experience! Beautiful Sites! Incredible sunset! Wonderful staff! Will do this again! A must do when in Key West!”

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5.2-Hour Sunset Sailing With Wine In Stock Island

★★★★★★★★★★5.0 · 94 reviews · 2 hours (approx.) · from $125

2-hour sunset schooner sail from Stock Island with wine, beer, and charcuterie included. Small group, attentive crew, big views.

“This was an awesome experience. The food and wine selection was great! Staff was awesome! And the views of the sunset were top notch! Would highly recommend!”

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6.Private 2-Hour Wind and Wine Sunset Sail in Key West

★★★★★★★★★★5.0 · 87 reviews · from $4,000

Private 2-hour Key West sunset sail on a 65-ft schooner with global wines, craft beer, and hors d’oeuvres, plus group photo time.

“Love the wine tasting, delicious appetizers and engaging crew. With the limited number of passengers, the service is first class.”

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7.Windjammer Champagne Sunset Sail

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

Sail the 2-masted Appledore II for a classic Key West sunset with champagne and a hands-on sail-raising tradition.

“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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8.Key West Wind and Wine Sunset Sail aboard classic Schooner

★★★★★★★★★★5.0 · 16 reviews · 2 hours · from $133

Classic schooner Key West sunset sail with 8 wines, premium beer, and gourmet appetizers in 2 hours from Opal Key Resort.

“Loved it all. very fun, knowledgeable, and skilled crew. Would go back every evening if I could.”

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9.Champagne Dolphin Sail and Reef Snorkel

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

Key West champagne catamaran with wild dolphin spotting and about an hour of reef snorkeling, small-group size, sanitized gear, easy coaching.

“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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10.Catamaran Champagne Sunset Sail

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

90-minute Key West catamaran sunset sail with unlimited champagne and beer, true sailing, and guided views of famous landmarks.

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

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

Two-hour Key West sunset sail on the Appledore Star with champagne, sangria, hors d’oeuvres, and a classic schooner sunset.

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

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