KEY WEST · SAILING
The best days on the water.
The 15 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“The staff was excellent as well as the entertainment! They made sure you had a great time and the appetizers were perfect. The captain was skilled and made sure everyone was safe and comfortable.”
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.
“The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!”
A 2-hour Key West catamaran sunset party with live music, unlimited drinks, and appetizers, plus prime water views and quick return for dinner.
“Great views, plenty of drinks, food. Good band played a lot of different genres.Staff where excellent. Smooth ride.”
Key West sunset sail with beverages included. Small group, attentive crew, harbor views, and a front-row look at the night celebration.
“There are bigger boats and longer trips and options out there for dinner cruises, etc. But we just wanted a nice 90 minute trek around the port with a small number of people on a sailboat. The bar service was a bonus to me. Captain Chuck and Lori were great hosts and were glad to…”
Sunset sail on America 2.0 in Key West: beer, wine, champagne, plated hors d'oeuvres, and views of Fort Zachary from the water.
“Great foods and lots of it. Tremendous staff, we are all very helpful and courteous. Great time and beautiful sunset. True sailing experience.”
Full-day kayak, snorkel and sail from Key West with a 65-foot schooner, wildlife refuge stops, and an all-inclusive buffet lunch.
“Great Day! The crew Tony, Anthony & Conner were personable and ensured that everything worked without a hitch. Felt taken care of the entire day. Highly recommend this tour!!”
Small-group Key West sunset sail with dolphin watching, premium wine, and chef-selected tapas on a luxury catamaran.
“This was the BEST dolphin cruise ever! Well worth the money. Sebago is the bomb!!🤗🥰 Will definitely do this cruise again!”
Sail Key West’s Historic Harbor on a champagne sunset catamaran with included drinks, captain-led viewing spots, and ocean views.
“You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to the 2 hour sail with live music and hors d’oeuvres.…”
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.
“The boat trip was amazing and the crew were very friendly, informative, and helpful. We really enjoyed the snorkeling and the fort, as well. The entire trip was organized well which made it easy to navigate meals, snorkeling, getting on and off the boat. We would do the trip again!”
Parasail 300 feet above Key West for an 8–10 minute flight, mostly dry, with optional ocean dip and digital photo options.
“Captain Alex and Garrison were fabulous....they went beyond for us....I'm going to send another tip to them”
Snorkel Key West’s living coral reef, enjoy rum punch and reggae on a catamaran, then watch the sunset from spacious decks.
“The cruise was a lot of fun and family friendly for my husband, my grown kids, and me. I personally would not bring kids under 13 unless they are experienced snorkelers, but there were young children in the water.”
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.
“Amber was a great Captain and her crew couldn’t have been nicer. They very knowledgeable and answered many questions, served snacks and drinks with a smile and the sunset was spectacular! 💯 will do it again.”
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.
“We really enjoyed being on the water during sunset. The boat had plenty of seating for all the guests and plenty of room to move around to the best areas for views. The live violin duet was a great accompiment to the views. The free pinot grigio and food were what would be expected on…”
The sailing ports worth the trip, grouped by the sea they sit on.
