SAILING WORLDWIDE
The best days on the water.
The 15 most popular key west sailing trips. What each sail costs, how long you are on the water, and which crews run it well.
Sail Key West at sunset on a spacious catamaran with live music, open bar, and hearty hors d’oeuvres. 2 hours, great views.
Most Popular“The perfect way to experience a Key West sunset. I would Highly recommend the Sebago cruise the captain and staff were excellent”
Half-day Key West snorkel sail on a 69-foot catamaran with reef time, gear included, and beer/wine plus cocktails on the return.
“The crew is great! They explained how to use the equipment and worked to make the experience a great one!”
Key West small-group sunset sail with wine and hors d’oeuvres: up to eight wines, five beers, and a calm, romantic 2-hour cruise.
“Such a great experience! Highly recommend We have been on Sunset cruises before that were rowdy and loud. Keeping it to a small group meant that this was a much more romantic experience.”
A 2-hour Key West catamaran sunset party with live music, unlimited drinks, and appetizers, plus prime water views and quick return for dinner.
“Fun and drinks great band. Weather was good got to see the sunset it was a great experience highly recommend”
Key West sunset sail with beverages included. Small group, attentive crew, harbor views, and a front-row look at the night celebration.
“The crew were accommodating but the cruise that was listed as 1 1/2 hours was only one hour. Drinks included were beer, white wine, prosecco and wine based margaritas”
Sunset sail on America 2.0 in Key West: beer, wine, champagne, plated hors d'oeuvres, and views of Fort Zachary from the water.
“The boat loads tight outside Schooner Wharf Bar. You need to get paper tickets at the window on the side of Schooner Wharf Bar about 30 before departure.”
Full-day kayak, snorkel and sail from Key West with a 65-foot schooner, wildlife refuge stops, and an all-inclusive buffet lunch.
“The day was perfect and the crew made sure we had the best time! Thank Brian, James and Connor we will be back!”
Small-group Key West sunset sail with dolphin watching, premium wine, and chef-selected tapas on a luxury catamaran.
“A fun evening cruising off Key West. The service was great. Capt. Dan and Gracie were great hosts. While we did not see dolphins, it was not for a lack of trying. The food and drinks were good!”
Sail Key West’s Historic Harbor on a champagne sunset catamaran with included drinks, captain-led viewing spots, and ocean views.
“It was great with the cruise being the best. Viator is the best to deal with. They go above and beyond to help ensure your booking is first rate,”
Small-group Key West snorkeling from a 54-foot sail yacht with sanitized gear, reef wildlife, and drinks included. 3 hours, $79.
“Captain Owen and Hunter were Awesome!!! Great snorkeling spot with a wonderful Crew. They kept us safe and met all of our drinking needs!”
Full-day catamaran trip from Key West to Dry Tortugas: Fort Jefferson tour, snorkeling with gear provided, and breakfast/lunch included.
“Nice boat ride. Helpful crew and knowlegeable tour guide. Not reall worth the money for what we got.”
Parasail 300 feet above Key West for an 8–10 minute flight, mostly dry, with optional ocean dip and digital photo options.
“What a wonderful family Experience!!! We did the 9am early bird, what a beautiful morning and a great time!!! Totally would recommend Fury to parasail!! Great company!”
Snorkel Key West’s living coral reef, enjoy rum punch and reggae on a catamaran, then watch the sunset from spacious decks.
“Awesome experience and great snorkeling! The crew and boat were great and the drinks and music were fantastic!”
Sail the America 2.0 schooner on a Key West sunset cruise with drinks, hors d’oeuvres, wildlife spotting, and a shot at the Green Flash.
“Fantastic sunset experience on a real sailing trip with cool drinks and even some really nice snacks! Very much recommended!”
Sail Key West at sunset on the Sandie Cat with live music, an unlimited open bar, and snack appetizers for a fun 2-hour cruise.
“It was exactly as expected....drinks and sunset on a big catamaran. Fortunately, it was not super crowded. The staff was great and the boat was clean.”
The sailing ports worth the trip, grouped by the sea they sit on.
