Sunset Cruises & Sails- Public
Wind & Wine
A guided tasting of fine wines from around the world, paired with select beers and light bites including artisan meats, cheeses, fresh fruit, and chocolate. This is a classic style of sail—perfect for guests with a touch of adventurous spirit and a love for discovering something new.
The Argo Navis - Luxury Catamaran
Sunset sailing on the historic schooner Appledore, where classic seamanship and a slower pace define the experience. Beer, Wine, Liquors and hors d'ouvres are served aboard by the friendly staff. Fully enclosed cabin with ample seating above and below deck for optimum comfort. This is on a stable catamaran which allows for a very smooth ride.
Champagne Sunset Sail Aboard Schooner America 2.0
A classic schooner sail at sunset, paired with champagne and front-row views of Key West’s evening skies. Great for those who don't mind a bit of a thrilling ride when there is wind. This is an old school schooner built for world-class racing. Lots of comfortable seating. Includes Champagne, beer and wine.
Sunset on the Schooner Appledore
Sunset sailing on the historic schooner Appledore, where classic seamanship and a slower pace define the experience. Beer, Wine, Liquors and hors d'ouvres are served aboard.
Sunset Sails & Cruises - Private
Private Sunset Cruise - Still Dreamin'
A private sunset cruise is one of the most relaxing and unforgettable ways to experience Key West. Enjoy calm evening waters as the sky turns brilliant shades of gold, pink, and orange, with plenty of time to unwind and take in the views. Ice chests and bottled water are included—just bring your favorite drinks and snacks if you’d like, and settle in for a private cruise with your group during the world-class Key West sunset.
Best for: Couples, proposals, small groups, and anyone looking for a private, laid-back sunset experience away from the crowds.
2 hour cruise, maximum of six guests.
Clothing optional sunset sail - Private
Clothing Optional Sunset - Sea Jazz
There’s no better way to experience Key West than from the water at golden hour. This 3-hour sunset cruise is a relaxed, clothing-optional private charter that blends easy sailing, ocean breezes, and unforgettable sunset views as the sky lights up over the horizon.
It’s the perfect balance of social and laid-back, with plenty of time to sip, unwind, and take in the natural beauty of the island from a completely different perspective.
Best for: Couples, proposals, small groups, and anyone looking for a private sunset experience away from the crowds — with the freedom to enjoy yourselves au naturel in a naturist-friendly atmosphere.
3 hour cruise, maximum of six guests.