$99 Island Jet Ski Tour

Key West Wind & Wine Sunset Sail

87 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



What's Included

What To Bring

Additional Info

Frequently Asked QuestionsFAQ



Average 4.94 out of 5 stars based on 87 verified reviews from Jet Skis Key West and TripAdvisor

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Well worth it!!!!
Michael S, Dec 2021 Verified
Great time, saw a beautiful sunset, and great crew. Would do it again in a heartbeat.
Great sail and wine
Jessica F, Dec 2021 Verified
Friendly staff! Great wine selection. Relaxing time, highly recommend
Awesome!! Had a great time. Highly recommend
Mary J, Dec 2021 Verified
Great wine and cheese selections. Fun, fun , fun!
Awesome Key West wine and sail adventure!
Carolyn W, Dec 2021 Verified
Absolutely spectacular crew wonderful night of sailing!
Sunset sale highly recommended
Martha B, Dec 2021 Verified
Gannon, Molly and Branza were exceptional hosts.the wine and appetizers were delicious. Branza at the helm, ensured a fun and safe sail. He was an excellent skipper. Molly was a superb second hand and hostess. Gannon made the tasting experience fun. would highly recommend.
awesome sailing
Karl P, Dec 2021 Verified
Beautiful sunset. Fantastic crew. Dream sailing.
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!

Still have questions?

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

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