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Key West Wind & Wine Sunset Sail

57 Reviews | Key West

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2 Hours (approx.)
Instant Confirmation


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



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Average 4.96 out of 5 stars based on 57 verified reviews from Inside Key West and TripAdvisor

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Chill Wind and Wine Sail Experience
Danielle G, Mar 2021 Verified
The crew were wonderful! The other guests were friendly, and the sunset...magical. A fun excursion for a Key West trip.
Awesome Sail...Wind, Wine n Cheese
Ray N, Mar 2021 Verified
Just WOW!! Amazing trip with great crew!! Perfect views of sunset, great company, great service, comfortable, great sailing...crew was very responsible and very qualified!!
awesome suset cruise!!
Edward L, Feb 2021 Verified
beautiful trip loved the crew captain and the flowing appetizers and wine!!
Awesome time with some awesome people!
Kyle R, Jan 2021 Verified
Recently we went on the wind and wine sunset cruise while in Key West for our honeymoon and it was awesome! The views were beautiful, the wine was delicious, and the staff was top notch! Would definitely go back again and highly recommend!
It was awesome!
Scott B, Jan 2021 Verified
We had a wonderful time. Fun crew and great wine!
Great time!
Jodi R, Dec 2020 Verified
Very good experience! Highly recommend!
Sunset wind and wine cruise
Jospeh C, Nov 2020 Verified
Everything was great The crew were great. The wine was good and food tastings were yummy. We had a nice sail and the sunset was beautiful.
Beautiful and amazing staff!!
James S, Nov 2020 Verified
The staff was very welcoming. The wine was very good lots of choices and did not taste cheap! Even if you are not a wine drinker like my husband he enjoyed the wines and they also had some great Selection of beers. The views were breathtaking!! Highly recommend this on your trip to the keys!
Wine and sunset cruise
Elizabeth C, Nov 2020 Verified
Great captain and crew!
Fun times at sea
Sara W, Nov 2020 Verified
Our captain and two guides were very knowledgeable about all the wine selections and they were very kind and fun hosts. I’m not the biggest wine drinker but still enjoyed views of the sunset and good music

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