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Key West Wind & Wine Sunset Sail

2 Hours (approx.)
Likely To Sell Out


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



Thanks for a great trip
Skyler Morgan, Dec 2019
Excellent trip with an amazing crew! The captain was energetic and thoughtful to everyone's needs. Once the sails were up there was a win and cheese tasting that was amazing. Thanks again!
Fantastic adventure on the open water!
Noah Owen, Nov 2019
Wonderfully intimate sail with a phenomenal and fun crew! Highly recommend to anyone in Key West!
great trip
Judy Smitherman, Nov 2019 Verified
we didn’t have much wind, but lots of wine! still a great time
Key west wind and wine sunset sail
Kevin Haslauer, Oct 2019 Verified
It was excellent. The crew was very personable and made it an even better experience!
What a perfect day
Wanda Shirley, Oct 2019
A fantastic evening. Above and beyond in all aspects! Can't wait to do this again in a few months when we return to Florida!
Wine sunset tour
Dawn Adams, Oct 2019 Verified
100% recommend this trip. Excellent wines, food and hospitality.
Simply enchanting West wind & wine sunset sail
Robert Walker, Sep 2019 Verified
The weather and sail were fantastic,combined with a super crew that helped make the trip we saw in a brochure come to life as an enchanting experience for both me and my wife . Ironically we saw a couple from our own state get married on the sail it was inspiring My wife has already told me where we will be renewing our vows
Awesome Sunset Sail
Daryl Greenfield, Sep 2019 Verified
Great time, good wine, great service.
Time of my life!
Gary Branstetter, Aug 2019
My friend and decided to get out on the water, and someone suggested this sunset sail. I could not recommend this more!!! I felt like I was in a movie, When and If is so stunningly beautiful, so chic, and being out on the water is amazing.
Key West wind and wine sail
Cynthtia Davis, Aug 2019 Verified
I’ve done this wind and wine sunset sail three times and I always enjoy it and meet some very interesting and friendly people! The crew each time has been courteous and fun. The wine and snack choices are excellent! Well worth doing!

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