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Key West Wind & Wine Sunset Sail

65 Reviews | Key West

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2 Hours (approx.)
Mobile Ticket
Instant Confirmation

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 4.97 out of 5 stars based on 65 verified reviews from Attractions Key West and TripAdvisor

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Key west wine and wind cruise
Mary L, May 2021 Verified
Beautiful cruise with great wines and appetizers. Crew was first rate look forward to doing it again soon
Great sunset sail
James M, Apr 2021 Verified
The captain and both mates were great. As soon as our wine glass or beer were empty there was another one to replace it. A schooner is the way to go for any kind of sail
Magical sunset and super sailors
Peter A, Apr 2021 Verified
We had an outstanding cruise,even the wine and snacks were great
Great sunset cruise!
Andie S, Apr 2021 Verified
This was an amazing experience!! It was a super cloudy day so the crew knew we were all bummed that we wouldn’t get to see a sunset. The crew went above and beyond to ensure we still had a great time, which we did! The beverage pours were very generous and the nomnoms were delicious! I’d definitely use this group again!!
Awesome and relaxing sunset sail
Samantha B, Apr 2021 Verified
We had a great time on the wind and wind sunset sail. We are not wine drinkers ourselves, but they had a pretty good beer selection also. The snacks they served were delicious, the staff was fun and awesome, and the views were unbeatable. It wasn’t crowded although the sail was “full”. Highly recommend for a more mellow and relaxing sail. Also, if you do come for the wine, they served 8 different kinds as a tasting and then people chose their favorites for the last hour. They definitely never ran out of any beer or wine either!
Great Key West Wind & Wine Sunset Sail
Sharon F, Apr 2021 Verified
Great Trip! There are fewer passengers and the crew was awesome! Was able go get great pictures!My only complaint is the when buying the tickets online, the directions provided are outdated. The store you check-in at was located closer to the beginning of the stores not at the end. Also, the hotel being used as a landmark in the directions has changed names.
Naznin A, Apr 2021 Verified
Excellent crew and hosts. Highly recommend it.
Beautiful evening sailing!
Erik M, Apr 2021 Verified
Great wine samples, hors d'oeuvres, and sights, including 2 dolphins!
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!!

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Product code: C-277559

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