KEY WEST · SAILING
The best days on the water.
The 11 most popular key west tours. 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“What a wonderful experience and the best way to see the sunset. The crew was extremely attentive and very friendly. Enjoyed getting to hear about their backgrounds, diverse as they are. Well worth the cost!!!”
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 boat was great as well as the captain and mates! I didn't see a lot of fish that was a bit disappointing. Other than that it was fun!”
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.
“I highly recommend this sunset sail. The wine and apps were delicious and the crew was great. It was such a nice touch to have a wine tasting while enjoying the beautiful sunset. I was really impressed with the selection of wines. I would highly recommend this sail for anyone visiting the area.”
A 2-hour Key West catamaran sunset party with live music, unlimited drinks, and appetizers, plus prime water views and quick return for dinner.
“It was super fun. Staff is great. Music was really good. Note that If you want to be able to sit get in line early.”
Key West sunset sail with beverages included. Small group, attentive crew, harbor views, and a front-row look at the night celebration.
“Wear comfortable shoes, it may get chilly in winter weather but a light sweatshirt is plenty to keep warm. The captain and fist Kate are very kind and well informed about sailing and Key West history.”
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 crew was wonderful! The snacks and drinks were a nice touch. It was so beautiful to be sailing on the water.”
Full-day kayak, snorkel and sail from Key West with a 65-foot schooner, wildlife refuge stops, and an all-inclusive buffet lunch.
“The crew are awesome, friendly and knowledgeable. The captain knows his stuff and provides education on how you can assure your safety and have a most enjoyable trip. He is a world class navigator and knows the Keys well.”
Small-group Key West sunset sail with dolphin watching, premium wine, and chef-selected tapas on a luxury catamaran.
“Great seeing the dolphins in their natural habitat. The boat crew were great and no point we didn't feel unsafe.”
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.
“We had a group of 12 with ages varying from 16 to 63! Everyone enjoyed the sail and snorkel experience! The hosts are helpful, patient, and a ton of fun! Highly recommend this adventure!!”
Full-day catamaran trip from Key West to Dry Tortugas: Fort Jefferson tour, snorkeling with gear provided, and breakfast/lunch included.
“Vía tour said I would get a veterans discount and no one knew anything about it when I got there. Don’t promise something and then not deliver.”
The sailing ports worth the trip, grouped by the sea they sit on.
