(855) 274-1023 Key West Questions? Call Us Now!

Key West Wind & Wine Sunset Sail

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



What's Included

What To Bring

Additional Info

Frequently Asked QuestionsFAQ



Fun even in the rain
Jonathan Bitting, Jan 2020 Verified
No sunset unfortunately and a few light rain showers did not dampen our enjoyment. Thanks to the delicious wine and hors d’oeuvres and fun repartee from Joe from Worcester we had a memorable evening. Capt. Wade from Colorado did a splendid job. We would highly recommend this sailing experience.
Key West Wind and Wine Sunset Sail
Dennis Crownover, Jan 2020 Verified
Highly recommend. We booked the tour as part of our 40th wedding anniversary celebration. We were not disappointed. Captain and crew were very entertaining, sharing stories and wine while we sailed to the sunset!Great fun, awesome pictures, a must do!
sunset wine tasting cruise
Thomas Oberdorf, Jan 2020 Verified
Fantastic, met great people and the crew was great as Well!!!!
Key West Sunset Sail with Danger Tours
Ken Mattern, Jan 2020 Verified
Hi, It turns out we couldn’t go because my wife developed a stomach bug. Danger tours cancelled our reservation, but Cool Destinations balked at refunding the $61 booking fee. We come to KW every winter. We’d more likely go with you folks next time we are here at if you’d kindly refund us the booking fee. There’s apparently a note on my file asking for just that. Thanks, Ken Mattern
What an amazing sunset
Owen Palmer, Dec 2019
Perfect from service to sail. I would highly recommend and repeat any chance I can.
Thanks for a great trip
Skyler Morgan, Dec 2019
Excellent trip with an amazing crew! The captain was energetic and thoughtful to everyone's needs. Once the sails were up there was a win and cheese tasting that was amazing. Thanks again!
Fantastic adventure on the open water!
Noah Owen, Nov 2019
Wonderfully intimate sail with a phenomenal and fun crew! Highly recommend to anyone in Key West!
great trip
Judy Smitherman, Nov 2019 Verified
we didn’t have much wind, but lots of wine! still a great time
Key west wind and wine sunset sail
Kevin Haslauer, Oct 2019 Verified
It was excellent. The crew was very personable and made it an even better experience!
What a perfect day
Wanda Shirley, Oct 2019
A fantastic evening. Above and beyond in all aspects! Can't wait to do this again in a few months when we return to Florida!

Still have questions?

We’re here to help. Call (855) 274-1023 to speak with a Destination Specialist.

Similar Tours & Activities

Key West Sunset Harbor Cruise

 2 Hours (approx.)
Best Rate

Key West Morning Mimosa Private Charter

 2 Hours (approx.)
Best Rate

Key West Wind & Wine Private Charter

 2.5 Hours (approx.)
Best Rate

Customers Who Bought This Tour Also Bought



Key West Split Fishing Charter

 4, 6 or 8 Hours


Miami to Key West Day Trip

 6 Hours in Key West