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The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy a guided tasting of fine wines from around the world, along with a selection of craft and domestic beers and light hors d'oeuvres including crudites, meats, cheeses, crackers, fruit, and chocolate.
With small group sizes, there’s plenty of space to move around and enjoy the view without the crowds. It’s perfect for a romantic date or a fun evening with friends—upscale, but never uptight.
What really sets this trip apart is the crew. They’re fun, welcoming, and passionate about what they do—ready to pour your next glass, share a story, or make sure you’re having a great time. Add in a Key West sunset, and you’ve got one of the most unique and enjoyable evenings on the water!
Public transportation options are available nearby
Suitable for all physical fitness levels
Minimum drinking age is 21 years
Must be 13 or older for this trip.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Danger Charters
Check-In at our storefront 1/2 hour before departure
Key West
Sailing nightly, we serve eight different fine wines from all over the world, usually four red, three white, and a Champagnoise. Wine drinkers love this cruise since it is virtually the only sailing excursion in the U.S. that serves “real” wine. In addition, an array of quality beer, and hors-d'oeuvres are also served, making the evening an unforgettable start to a great Key West night!
Light refreshments
Wine tasting
Unlimited beer, wine and soft drinks
Hors d'oeuvres complementing the wines
Gratuities
Enjoy a sunset sail like no other with fines wines from around the globe and hors d'oeuvres to compliment them. Great for that special occasion.
1.357 đánh giá
Tổng số đánh giá và xếp hạng từ Viator & TripAdvisor
Eric B,,30 thg 1, 2026
- Đánh giá từ Viator
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 and brie. I loved how the wine tasting was treated like a ‘sail around the world’ with wines from many different places. The crew was willing to answer our many Key West questions, fill our glasses, offer appetizer seconds and sometimes even more to the passengers, as well as engage in our friendly banter. They even offered blankets to cold guests. We would absolutely sail with Danger and this crew again!



762sherrit,,29 thg 1, 2026
- Đánh giá từ Tripadvisor
The sunset sailboat cruise was very nice. The Captain and his crew were very friendly and helpful. It was a very relaxing experience with a nice variety of small bite food and wines to sample. The crew was even prepared to help with the minor red wine spill that I’m guessing happens occasionally! The sunset and views of Key West were amazing!
N1065QZmarior,,27 thg 1, 2026
- Đánh giá từ Tripadvisor
It was a cloudy day so the sunset wasn't spectacular. The sailboat got off a little late but once on our way, we had to turn around and pickup a late arriving couple...so it was even later. Bring a windbreaker as it can get cool. The wine and hors d'oeuvres service was good for snacking and nicely paired with wines, providing a good mixture of sweet and savory choices. But sit in the front as it seemed like they got more second pours of wine. I would recommend as a fun and relaxing way to be out on the water and look at the town from a completely unique vantage points.
Nancy V,,26 thg 1, 2026
- Đánh giá từ Tripadvisor
The cruise was wonderful. Wine was plentiful and the appetizers delicious. My only complaint was there 2 people too many on the boat for the number of seats. We got in last and had to somehow squeeze 4 people in a spot that fit 2 people. It really was a great cruise!
Fred M,,25 thg 1, 2026
- Đánh giá từ Viator
What a great time. Enjoyed all the wines and hors d oeuvres. They kept on coming. Tony and the crew told great stories they were friendly and on it! Great job you all! Thanks for beautiful sunset pics and a great sailing!
Theresa C,,25 thg 1, 2026
- Đánh giá từ Viator
Friendly, knowledgable staff, excellent wine, plenty of options to drink aside from their wine. Ample amount food
Janice P,,24 thg 1, 2026
- Đánh giá từ Tripadvisor
Great Captain and crew. Wine tasting and lite bites were perfect! Thank you for being attentive to us on the back of the boat.
horizons77,,24 thg 1, 2026
- Đánh giá từ Tripadvisor
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres was outstanding! The Captain Mika and the crew Laura and Paul were very personable and so nice. They explained the food and wine (or other drinks) before bringing it to you. The sailboat ride was smooth and the sunset was beautiful. We would definitely do this again! Thank you again Danger Charters!



jamesdW166XW,,21 thg 1, 2026
- Đánh giá từ Tripadvisor
Amazing experience. It was too cloudy to see the sun set, but unforgettable views of sea & sun above the clouds. Wine and hors d'oeuvres were very good. Crew was friendly and professional.


jennifersQ1998SB,,20 thg 1, 2026
- Đánh giá từ Tripadvisor
Great trip! Lexi , Captain Mary and cooper did a great job and we had a blast. Would highly recommend it ! Sunset views were incredible
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