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Key West Wind & Wine Sunset Sail

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

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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 113 verified reviews from Key West Water Sports and TripAdvisor

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A worthwhile adventure
Frank C, May 2022 Verified
Relaxing and very enjoyable. The crew was fantastic. Not too crowded, and engaging conversation with other passengers. Tasty hors d’oeuvres and a good selection of wines. And lest I forget, a fantastic sunset!! Highly recommended
Awesome Sunset Cruise
Michael D, May 2022 Verified
It was our 30th anniversary and had an awesome trip - the wine selections were great and so were the appetizers. The staff were a lot of fun.
Key West Wind & Wine Sunset Sail
Jaime G, May 2022 Verified
Highly recommend taking this sail. The wine and horderves were excellent, the sail and sunset were amazing and the crew were highly professional, fun and toned in to everyone's preferences.
Awesome Key West Sunset tour
Wendy S, May 2022 Verified
It was a great trip. Joe was a hoot … everyone was absolutely awesome. Great wine and good munchies (probably could have a bit more considering the amount of wine).Loved the smallness of the tour!
Excellent service
Chris L, May 2022 Verified
If you are looking for a more personal experience then look no further. This sunset cruise more than delivered on overall experience and customers service. The wine and snacks where wonderful. The best part was the smaller crowd allowed for you to really enjoy the sunset. The boat crew was phenomenal and made every effort to make sure all aboard had a great time!!!!
Amazing sunset wine and sail
Stephen M, May 2022 Verified
We highly recommend this sunset wine and sail excursion. It was an amazing experience from start to finish. The crew was great! From the wine, to the beer and all the passed appetizers in between the crew was consistently making sure we were satisfied. The sunset was beyond beautiful. It was the perfect way to celebrate our 30th wedding anniversary! It was the highlight of our trip ! We are already talking about going back and will book this again. We may even do it more than once. Thanks for making it a great memory! Thank you! Steve & Wendy from Massachusetts
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.

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Product code: C-277559

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