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Key West Wind & Wine Sunset Sail

52 Reviews | Key West

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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



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Average 4.96 out of 5 stars based on 52 verified reviews from Tours of Key West and TripAdvisor

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Great time!
Jodi Roznowski, Dec 2020 Verified
Very good experience! Highly recommend!
Sunset wind and wine cruise
Jospeh Cogozzo, 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 Smith, 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 Crutsinger, Nov 2020 Verified
Great captain and crew!
Fun times at sea
Sara Weber, 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
Wine sunset sail
Andrea Breslin, Oct 2020 Verified
We had a blast. Wine was yummy and the crew great.
Our Response, Oct 2020
Andrea, thank you very much for your positive feedback on the Key West Wind & Wine Sunset Sail. We’re glad you had a good experience and hope to see you again soon.
Awesome Wind and Wine Cruise
Brian Cox, Sep 2020 Verified
Well organized, friendly staff, good wine and snacks.
Awesome Key West Wind and Wine Sunset Sail
Denise Gayle Smith, Sep 2020 Verified
Loved it! Must do in Key West!
The Crew Made the Trip
Mike Michaleson, Jul 2020 Verified
Brian, Meg, and Bronza made sure we had a great time and treated us like we were old friends. The wind, wine, and sunset were as promised (I don’t know how they controlled two of the three).Very well worth the cost! Great experience!
Our Response, Jul 2020
Mike, thanks for leaving feedback on the Key West Wind & Wine Sunset Sail. Our staff are very passionate about providing a unique cruising experience, we're glad you thoroughly enjoyed it. We're glad you enjoyed the experience, the sunsets are truly amazing and we look forward to welcoming you back again next time you're in town.
Great time
Raul Cortes, Jul 2020 Verified
Great crew and captain!
Our Response, Jul 2020
Raul, thanks for leaving feedback on the Key West Wind & Wine Sunset Sail. We're glad you enjoyed the night out with us and hope to see you back on board again in the future. Thanks a lot for booking your tour on Tours of Key West!

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