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Key West Wind & Wine Sunset Sail

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

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2 Hours (approx.)
Mobile Ticket
Instant Confirmation


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 106 verified reviews from Tours of Key West and TripAdvisor

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Amazing wind and wine sunset cruise!!!
LuAnn W, May 2022 Verified
This sunset cruise was one of the highlights of our key west vacation. The crew and ship were the best!!!!
Awesome Sunset Cruise!
Linda W, May 2022 Verified
The Key West Wind & Wine Sunset Cruise was so fun & relaxing! The crew were professional & accommodating. They helped us get many beautiful pics. We enjoyed the nice selection of wines & beers from Derek who kept our glasses filled as well as the hors d'oeuvres from Gonzalo. It's not easy pouring & serving on a sailboat but they pulled it off! With Brian at the wheel, it was smooth sailing! Highly recommend!
Amazing sunset sail and wine tasting trip!
Jeremy N, Apr 2022 Verified
We had a great time on our sail! The boat was nice, the crew were all so kind, helpful, knowledgeable, and made sure we had the best time. The wine tasting was so much fun! Can’t recommend this experience enough!
Great way to have wine on the ocean
Pamela N, Apr 2022 Verified
I took my parents on this cruise and we all loved it. The captain and crew were fun and happy people. We drove out away from the dock and settled in to float for a while. They served us a generous amount of tastings and then a full glass of our choice. The apps were cheese and fruit and meat on toothpicks with all the different cheeses. There was also yacht rock playing in the background at the perfect sound level to enjoy but also be able to have conversations. Perfect for floating around and tasting wine. We enjoyed the gorgeous sunset and then drove back to the dock. We’ve been coming to Key West for many years and the three of us agreed this was our favorite expedition yet! We will be back next year.
Wonderful way to end our trip!
Alexandra C, Apr 2022 Verified
We chose to do this on our last night in Key West and it was better than expected. Crew was amazing and all the wines and cheese pairings were delicious! Definitely recommend if you are looking for a relaxing and enjoyable evening on the water.
Perfect sunset cruise
Susan N, Apr 2022 Verified
Smooth sailing! Delicious wine and food in a casual atmosphere. Friendly crew, and the service was perfect.
Fun time and great wine
Stuart A, Apr 2022 Verified
Friendly crew and a great wine.
Great time. Crew was excellent. Will do again.
Mari G, Mar 2022 Verified
Wine tasting , skewers, a lot of fun people. Won’t hesitate to do again.
Key West Wind and Wine
Timothy F, Mar 2022 Verified
Crew was professional, friendly and knowledgeable on the local history. Our group had a great time. Even with little wind
Great Sunset Experience!
Vanessa W, Mar 2022 Verified
Great wines, superb service, wonderful Captain and Crew. We would book this again, one of the highlights of our Key West Vacation.

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We’re here to help. Call (855) 274-1023 to speak with a Destination Specialist
Product code: C-277559

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