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Key West Wind & Wine Sunset Sail

80 Reviews | 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



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Frequently Asked QuestionsFAQ



Average 4.95 out of 5 stars based on 80 verified reviews from Tours of Key West and TripAdvisor

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This was the most fun thing we have done in Key West
Loretta B, Nov 2021 Verified
We had a great time. Bryan, Joe and Nichole were great host. The sail, the views, and the wines were incredible!!
Amazing sail
Patricia T, Nov 2021 Verified
The weather was iffy but the Captain sailed us around the storm clouds. Joe and Ellen were perfect hosts. It was the highlight of our trip to the Keys
Would do again in a minute
Karen M, Oct 2021 Verified
Awesome trip THE BEST!!
Wind and Wine Sail was awesome
Diane L, Oct 2021 Verified
Our experience was lovely! Rose and Logan (crew) were very entertaining and made our sail special. Captain Mary was also very professional. We would highly recommend this wind and wine tour!
Awesome sunset sail wind & wine
Vicki P, Sep 2021 Verified
The captain and crew were amazing, friendly and fun!
Great Sailing and Wine Selection
Drew L, Sep 2021 Verified
Crew was outstanding. Did their homework on the wine selections and paired well with the cheese selections too. Variety of beer and coolers if wine’s not your jam. Thanks for a terrific evening with a lovely sunset in the Keys. Highly recommended
Captain and his crew were awesome
Joseph B, Sep 2021 Verified
Great sunset sail, the captain and his crew were informative and attentive. We all had a great time.
No better event for a sailor or landlubber
John R, Aug 2021 Verified
Such a great sail. Loved this as I helped raise the mainsail in this awesome schooner
Amazing time on Sunset Wind and Wine Cruise!
Kami T, Jul 2021 Verified
We had an amazing time on the Sunset Wind and wine Cruise! The team did an amazing job navigating around a storm to insure we saw the sunset and had a spectacular view! The glass was never empty and there were enough appetizers to go back for seconds. Very relaxing and would definitely do again!
Wonderful experience
Julie T, Jun 2021 Verified
Friendly crew; very enjoyable experience!

Still have questions?

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

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