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

Key West Wind & Wine Sunset Sail

70 Reviews | Key West

Loading Options

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 4.97 out of 5 stars based on 70 verified reviews from Attractions Key West and TripAdvisor

5 stars
4 stars
3 stars
2 stars
1 star
Wonderful experience
Julie T, Jun 2021 Verified
Friendly crew; very enjoyable experience!
Great time. Loved it
Brian S, Jun 2021 Verified
Lots of fun
Perfect Sunset Cruise in Key West
Teri W, May 2021 Verified
We were looking for a nice, relaxing evening on our last night in Key West and this sunset cruise was perfect. The sail boat itself was a charming vessel that held about 20 of us including the crew. The crew was fun, friendly and knowledgeable. The wine quality was better than most served on these types of excursions and were accompanied with perfect appetizers. Please let Captain Bronza and mates Nico and Dan know that we appreciate their great service! It was a great night!
Beautiful and Fun
Matt B, May 2021 Verified
Beautiful Sunset with a fun Crew
Kerry Y, May 2021 Verified
My mom and I had a wonderful time on the Wind and Wine Sunset Sail. The crew was so much fun and the experience was unforgettable. Definitely my favorite part of my trip to Key West.
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!

Still have questions?

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

Similar Tours & Activities

Key West Sunset Harbor Cruise

 2 Hours (approx.)  Hotel pickup offered  Instant Confirmation


Key West Backcountry Safari

 6.5 or 4.5 hours (approx.)  Instant Confirmation

Key West Morning Mimosa Private Charter

 2 Hours (approx.)  Hotel pickup offered  Instant Confirmation

Customers Who Bought This Tour Also Bought

Key West 2 Seater Scooter Rental

 Starting at 3 hours  Instant Confirmation
Best Rate

Key West Helicopter Tours

 Varies  Instant Confirmation
Best Rate

Key West 22′ Angler Panga Boat Rental

 4 or 8 Hours
Best Rate