Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

Overview

Available languages

English

2 hours

Mobile ticket

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!

Additional Info

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.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

What To Expect

Danger Charters

Check-In at our storefront 1/2 hour before departure

20 minutes • Admission Not Applicable

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!

1 hour 40 minutes • Admission Not Applicable

What‘s Included

Light refreshments

Wine tasting

Unlimited beer, wine and soft drinks

Hors d'oeuvres complementing the wines

Gratuities

Options

Departure

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.

Reviews

4.92

1,367 reviews

Total reviews and rating from Viator & Tripadvisor

1301

Highlight of trip
Katie B,,Feb 10, 2026
- Review from Viator
5.00
What an amazing experience! The wine was plentiful, the snacks were delicious, and the view of the water and sunset were unbeatable. Mary, James, and Connor were professional and friendly. All around absolutely worth doing this!
Danger and wine
Renita D,,Feb 9, 2026
- Review from Viator
5.00
The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!
This sunset cruise was amazing
Sam J,,Feb 9, 2026
- Review from Tripadvisor
5.00
This experience was unforgettable and amazing. The crew was so friendly. The sunset was gorgeous and the snacks were delicious. We will definitely go again the next time we visit Key West you will not regret taking a cruise with danger charters
Smooth Sailing
April G,,Feb 9, 2026
- Review from Viator
5.00
Great experience on the Key West Sunset Sail and Wine Tasting. Beautiful sunset and smooth sailing. The crew was professional and attentive. The wine selection was good and paired well with simple hors d”oeuvres. We’d book again with Danger Charters!
We had a pleasant time on...
Kelley R,,Feb 7, 2026
- Review from Viator
3.00
We had a pleasant time on the sunset cruise and appreciated the wine selection and snacks. However, we were disappointed that the captain didn’t give both sides of the boat a chance to view the sunset. For the premium price, I expected a more inclusive experience. I’m not sure I’d recommend it given the other, more affordable options available.
Celebrate the Key West life!
A266LEdebrap,,Feb 6, 2026
- Review from Tripadvisor
5.00
Terrific wines from Italian prosecco to Australian Cabernet Sauvignon, delicious appetizers that appropriately paired with them, a gorgeous sunset viewed from a schooner, and an efficient and friendly crew, all combined for an unforgettable evening.
Brian and team were...
Abby S,,Feb 3, 2026
- Review from Viator
5.00
Brian and team were wonderful. We had a great time. They had some lovely wine and appetizers. The sunset was amazing as well.
Even in chilly weather, they made for a great evening…
corinnes881,,Feb 2, 2026
- Review from Tripadvisor
5.00
Lovely… great crew… grand selection of wines…. Professional and personable….even if very cold environments they made the evening Iovely
Perfect Sunset Sail with Awesome Crew
Eric B,,Jan 30, 2026
- Review from Viator
5.00
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!
Lovely sunset cruise at Key West
762sherrit,,Jan 29, 2026
- Review from Tripadvisor
5.00
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!