Best Key West Sunset Sails


Key West sunset sail
Photo by Mary Veal Photography

Anyone will tell you that a Key West sunset is the #1 must see on the island. Mallory Square is a great stop to celebrate the end of another sunny day, but if you’re looking to get away from the crowds, a sunset sail is for you. With nothing between you and the view, you’re sure to walk away in awe of the natural beauty our little island has to offer! Without further ado, we give you the best sunset cruises in Key West.

Fury Water Adventures

If you came Key West for a good time, it doesn’t get better than Fury’s Commotion on the Ocean cruise! Key West’s best musicians play live music to sing and dance to as you watch the sun go down and the island nightlife begins. Drinks, including beer, wine, champagne and margaritas, as well as fresh appetizers are provided.

Danger Charters
Danger’s Wind & Wine is perfect for those who want a more relaxed or intimate setting to view the Key West sunset. Step aboard their historic style schooner for a memorable evening filled with laughter, good wine, and delicious appetizers. Danger’s phenomenal staff ensures a relaxed and romantic atmosphere, serving international wines, beer and thoughtful hors d’oeuvres. They are even happy to arrange for a proposal on the ship!

Sebego Captain’s Choice

Delicious tapas, fine wines and beers and an intimate atmosphere make the Sebago a great choice for a sunset sail. The small catamaran enables the guests and crew to interact for fun and shared experience. Superb drinking, excellent eating and good company make this a magical voyage.

Blu Q

Known for being extremely LGBT+ friendly, the Blu Q heads out to view the Key West sunset aboard a catamaran.  Captain Steve has an obvious passion for sailing and has been sailing our island’s waters for the last 20 years. Complimentary drinks, including champagne, wine and beer are provided and hors d’oeuvres including shrimp cocktail and a cheese plate are passed. All that and good music makes the experience top notch!

Schooner Jolly II Rover

Ahoy! This historic style pirate ship will take you back in time with red sails, a skull and crossbones flag, and a shot fired from a real cannon! Join the Jolly II Rover’s swashbuckling crew for a truly unique Key West sunset. This boat is both family friendly and dog friendly, but keep the sound of the cannon firing in mind. Guests are encouraged to bring their own rum and ale and anything they would like to eat. Bottled water, ice chests, cups and bottle openers are provided. It’s a pirate’s life for us!

Sunset Watersports

The dinner cruise aboard a Sunset Watersports catamaran is a great alternative to dinner reservations on land. Help yourself to the Caribbean roasted pork, sweet plantains, fish fry and more while listening to the sound of live Caribbean steel pan music from the deck! Complimentary draft beer, wine and soft drinks are provided for those who do not buy a dinner ticket, but those with a dinner ticket also have access to an open bar with unlimited mixed drinks and champagne. As well, there is a premium cash bar where you can buy top shelf liquors. bottled beer and frozen drinks. You can upgrade to a dinner ticket if you like, right on the ship.

Classic Harbor Line

Sailing in every winter from New York, the Schooner America 2.0 is an 1851 revival with plenty to offer. Enjoy the romance of an historic tall ship. Relax with a complimentary glass of champagne, wine, beer, or soft drinks as you glide through the island waters. Passed hors d’oeurves are provided by the crew and they are happy to chat with you about the ship and its history.

Whether you’re looking for a party or you want to relax with a loved one, there is a sunset cruise for everyone in Key West! Click here to check availability for your next island adventure.