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“Great staff, fun apps and delish drinks. Boat is nice and big with plenty of room up top and the covered down below”
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.
“Very attentive staff on the boat! Generous wine pouring. Nice variety. Beautiful cruise. Check in process was slow.”
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.
“Hunter and the Captain were Great Hosts. Made sure you are Hydrated Definitely recommend This 90 minute Sunset Tour”
Sunset sail on America 2.0 in Key West: beer, wine, champagne, plated hors d'oeuvres, and views of Fort Zachary from the water.
“Such a peaceful evening on the water! The crew was so friendly and helpful! Great way to wrap up our week in the keys!”
Full-day kayak, snorkel and sail from Key West with a 65-foot schooner, wildlife refuge stops, and an all-inclusive buffet lunch.
“Great experience and a GREAT value for the price. We set sail with Bible, Anthony, and Mary and had a lovely day. We learned a bit about the history of of Key West, snorkeled, and kayaked around mangroves where we saw plenty of fish, turtles, and even a nurse shark!”
Small-group Key West sunset sail with dolphin watching, premium wine, and chef-selected tapas on a luxury catamaran.
“The experience did not live up to the title, but, it was enjoyable. I was expecting more dolphin watching. I guess I should call that - looking for dolphins. There is not really a search. The boat goes along a set path (you can see buoys showing the way) and then once you get to…”
Sail Key West’s Historic Harbor on a champagne sunset catamaran with included drinks, captain-led viewing spots, and ocean views.
“Our family from youngest to oldest came on the cruise and enjoyed the peaceful tranquility. Crew was attentive and outstanding!”
Small-group Key West snorkeling from a 54-foot sail yacht with sanitized gear, reef wildlife, and drinks included. 3 hours, $79.
“The captain and mate were awesome. Jared did everything he could to make it a great experience. Unfortunately we didn’t see anything. And the reef was all dark colors and so were the fish. Location could have been better”
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.
“Had an amazing experience, very friendly staff. This is was our first time and the staff explained the process very clearly.”
Snorkel Key West’s living coral reef, enjoy rum punch and reggae on a catamaran, then watch the sunset from spacious decks.
“Super fun, super crazy ! What an experience ! It was a little intimidating but over all it was super fun.”
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.
“Very good food ❤️ The captain let us drive the ship. Amazing experience!”
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 a Great boat ride with good food and awesome music. Staff were super friendly and accommodating”
The sailing ports worth the trip, grouped by the sea they sit on.
