Key West Wind & Wine Sunset Sail

131 Reviews |
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Badge of Excellence |
Key West, USA

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2 Hours (approx.)
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Keeping you safe during COVID-19
What you can expect during your visit
Face masks required for guides in public areas
Face masks required for travelers in public areas
Hand sanitizer available to travelers and staff
Regular temperature checks for staff
Regularly sanitized high-traffic areas
Social distancing enforced throughout the experience
All boats regularly sanitized


The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running.


  • Rated #1 on Trip Advisor for three years running Beautiful sailing boat
  • Exclusive Trip with just over twenty passengers
  • Amazing Key West sunset views
  • Attentive and Friendly Crew



What's Included

What To Bring

Additional Info

Frequently Asked QuestionsFAQ



Average 4.95 out of 5 stars based on 131 verified reviews from Cool Destinations and TripAdvisor

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Awesome sailing experience
Daniel L, Jan 2023 Verified
The staff was awesome and Captain was very cool. Will definitely do it again!!
Great views, great wine, great time!
Lauren A, Jan 2023 Verified
We went on this sail with one other couple that we knew from home. We met two more great couples and had a wonderful time. The weather was perfect, the wine selections were great. Passed hors d'oeuvres were delicious and plentiful. The boat was comfortable. The crew was friendly and helpful. All in all, I would do this again in a heartbeat.
Leda S, Dec 2022 Verified
Awesome Cruise and Awesome crew of young women! Would definitely recommend this sunset cruise to anyone visiting Key West.
Key West Wind and Wine Sale
Robert M, Dec 2022 Verified
This is an awesome trip. The crew went out of their way to make it fun by describing each wine, distributing hors d'oeuvres and making sure that we were comfortable. Luckily, we had enough wind to actually sail. We could do this trip over and over. Highly recommend this.
Key West wind and wine sunset sail.
Jim B, Nov 2022 Verified
Had a great time on the sunset sail. The food and wine were terrific, the sailboat and sunset were spectacular.
Super Trip - Crew is Outstanding!
William F, Nov 2022 Verified
Everything about the trip was great. Great crew, wine and fellow passengers.
Fabulous Wine and Sunset Sail in Key West
Eliza B, Nov 2022 Verified
We had a fantastic time on the sunset sail. The boat was beautiful, as was the sunset, and the crew was friendly and helpful. The hors d’oeuvres and wine were delicious.
Nice sail
Kate G, Oct 2022 Verified
The staff and crew were super nice and friendly. It rained on us for the last 45 minutes and there was minimal cover from the elements. A nice touch would have been ponchos, but really that should have been up to me. Wines were good, apps were good. More of a seated adventure than I was expecting but overall a good trip.
Great trip with danger charters
Amy K, Oct 2022 Verified
It was a beautiful night on the water and the staff was very attentive. Nice variety of wines and hors d'oeuvres. If you do not like wine they had a variety of different beers. I would definitely recommend this for a sunset Cruise
Awesome key west wine and sails excursion!
Lisa S, Sep 2022 Verified
Awesome excursion ! Wine was good, service and hor - d’oeuvres were good ! Boat was clean . Worth the money, fun time .

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Product code: C-277559

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