Private Sunset Sail: Key West Wine Experience

Embark on a private sunset sail in Key West. Savor global wines, beers, and hors d’oeuvres aboard a 65-foot schooner. Perfect for groups up to 26.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • 255 Front St - This is a two-hour sunset sail on one of our 65-foot schooners. You and your friends will enjoy sailing the waters of Key West while watching the sunset into the ocean. A variety of wines from around the world will be served as well as an assortment of craft, IPA’s, import and domestic beers. There will be hors d’oeuvres to…
What's Included
  • Bottled water
  • Snacks
  • Variety of assorted cheese skewers (Caprese, Brie with honey)
  • Alcoholic Beverages
Meal Options
  • Hors d’oeuvres - We offer a variety of assorted cheese skewers from Caprese to Brie with lightly drizzled honey.
Additional Information

Embark on a private sunset sailing expedition with your group, (Max 26 Participants), indulging in global wines and a selection of beers. Set sail on a 65-foot schooner, admiring the sunset as it dips into the sea. Enjoy a variety of appetizers being served throughout the journey. It’s the perfect avenue to sail privately with your friends, family, or colleagues.

Location
255 Front St
Front Street
We are located on the side of the Opal Key Resort hotel. Check in time for your excursion is 30 minutes prior to departure.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(93 Ratings)
5 stars
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1 star
Darinmartell
Sep 9, 2025
We will not come to Key West without doing a sunset cruise with Danger! - Danger is the ONLY way to experience Sunset! This is our third time. Great people, great food, and great drinks! We won’t come to Key West without a trip with Danger!
Review provided by Tripadvisor
Amy
Aug 31, 2025
Our favorite Sunset charter with wine and cheese - Amazing night the staff was amazing. Beautiful wines with beautiful cheese our favorite trip we do it every year we come to Key West. Great company great people beautiful sunset.
Review provided by Tripadvisor
Pamela
Jul 31, 2025
Fun, fun, fun! - Fabulous everything! Geogeous sunset! Awesome crew! Perfect wine selections! Loved e very moment - so relaxing! I have the most beautiful sunset pictures possible. I was so happy with this two hour cruise. Everyone was happy and congenial.
Review provided by Tripadvisor
Amy
Jun 23, 2025
A weekend getaway - It was a very enjoyable experience. Captain Luke, Francisco and Sanvy. They were all great hosts. The wine and food were well done!
Review provided by Tripadvisor
Daytrip07889743051
Jun 2, 2025
Cut the motor and raise the sails - Absolutely the best sunset cruise that my wife and I have been on. Wine tasting exceptional. If you don't care for wine, beer and soda on hand too. Crew went above and beyond. Impressed by the variety of meats, cheeses and crackers supplied. Sunset was fantastic. A must do for couples when in Key West.
Review provided by Tripadvisor
Lobo6973
May 12, 2025
An annual tradition for us! - Love the wine tasting, delicious appetizers and engaging crew. With the limited number of passengers, the service is first class.
Review provided by Tripadvisor
Barbarabh4069rx
May 7, 2025
Our Third Cruise - This was our third sunset, wine tasting, cruise with Danger in the last two years. Comfortable boat, fun and accommodating staff, good wine, tasty food, beautiful sunset.
Review provided by Tripadvisor
Jameso2969
Apr 30, 2025
Welcome Party success - We were on a chartered Wind and Wine for our daughter and son-in-laws Welcome Party. It was fabulous, as always (we’ve sailed with them countless times). Captain Brian and crew were delightful and made this celebration a cherished memory.
Review provided by Tripadvisor
Departure07322784294
Apr 20, 2025
Wine and sunset - Staff is always great.. good cruise and beautiful sunset. Clean boat. Have done several cruises and will return to them.
Review provided by Tripadvisor
G6636wvdavidd
May 18, 2025
Nice trip but cheesy. - The crew was friendly and there was a good variety of wine. The atmosphere was reserved without the obnoxious crowds. One thing to improve upon was the food. There was not many choices and one can only have so many cheeses. Some prosciutto would have been nice. Even fresh schrimp or cold seafood dip. Still a pleasant trip. We met some nice people aboard which is always a plus.
Review provided by Tripadvisor
From $4,000 (Per Boat)
up to 1 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).