Key West
The sailing trips: tall-masted schooners and modern cats running reef days, day sails and the sunset ritual. Wind has always been this island’s native engine.
Experience a memorable Key West sunset aboard a spacious catamaran with live music, premium drinks, and delicious hors d'oeuvres for a relaxing evening on the water.
Most Popular“It is a wonderful experience! Great music, food & beverages! The sunset was magnificent!! Highly recommend!”
Experience Key West’s vibrant coral reef on a 3-hour snorkel sailing trip with professional guides, unlimited drinks, and friendly, knowledgeable crew.
“It was exactly as we anticipated. There were a lot of people on the boat, but the staff was great and well prepared. The equipment they provided was in good condition, but I felt the water wasn't that clear and I had a hard time…”
Experience a cozy sunset sail off Key West with wine, beer, and gourmet snacks. Perfect for relaxed travelers seeking scenic views and quality drinks.
“Wonderful experience even though there was not much wind the sails were up and the atmosphere and view were phenomenal. Great crew wine was flowing. Food was flowing was a wonderful experience that I would highly recommend.”
Experience a vibrant sunset cruise in Key West with live music, unlimited drinks, and appetizers—perfect for relaxing and meeting new friends.
“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.”
Experience a tranquil sunset from a small sailboat off Key West, with drinks included, attentive crew, and stunning water views—ideal for relaxed evenings.
“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…”
Experience a relaxing sunset sail in Key West aboard a classic schooner with complimentary drinks and hors d'oeuvres. Perfect for a romantic or scenic evening.
“Wonderful experience! This was the best Sunset cruise we have taken. The staff was great. I highly recommend.”
Experience a full day of sailing, snorkeling, and kayaking in Key West with all-inclusive food, drinks, and expert guides. Perfect for active water lovers.
“Loved the crew! We were canceled from the original full day charter. But at the last minute we were added to a half day. Micah and Katie were very helpful”
Experience a relaxing sunset sail in Key West with dolphin sightings, tapas, and premium wine. A cozy, scenic cruise perfect for nature lovers and foodies alike.
“This is a great opportunity to see Key West's beautiful dolphins. Luckily, we saw several dolphins and enjoyed every moment while being entertained by the knowledgable crew.”
Experience Key West’s stunning sunset from a luxurious 69-ft catamaran, enjoying included wine, champagne, and scenic views in a relaxed, authentic setting.
“Great experience. Got sea sick but a god cruise! Expect a lot of people drinking and taking in the views. Just very light apps. A musician as well.”
Discover the Key West Reef Snorkel & Sail Adventure, a small-group cruise offering stunning reef views, friendly guides, and great value for memorable water fun.
“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!!”
Discover the beauty of Dry Tortugas with this full-day catamaran trip from Key West, featuring snorkeling, historic tours, and stunning ocean views.
“One of the more beautiful beaches we have ever been to. Boat trip is five hours round trip so bring a book or games. But the island is well worth it. Take the tour. Crew was great. The guide was knowledgeable but not overwhelming.”
Experience soaring above Key West’s turquoise waters with a safe, fun parasailing trip—breathtaking views, friendly staff, and photos to remember.
“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!”
Experience snorkeling over Key West’s only living coral reef, followed by a sunset sail with reggae music and drinks, all for about $59 per person.
“Great crew, very attentive, snorkeling was amazing! They even have reef friendly sunscreen. Everything you need!”
Experience a stunning Key West sunset on a graceful schooner, enjoy drinks, hors d'oeuvres, and wildlife sightings—all in 2 relaxing hours.
“Great crew! Fun experience sailing out of the marina and out in to the open ocean. My family of four (two teenagers) loved this trip so much that we did it twice during our week stay in Key West. We had the same captain (Janet)…”
Experience stunning Key West sunsets with lively music, unlimited open bar, and delicious appetizers on this 2-hour catamaran cruise for $79.95.
“The Sunset sip and sail was awesome! They had an open bar and free appetizers available to snack on, and an option to upgrade to a full dinner for a small additional cost. But let's face it, you book this for the experience of sailing…”
Schooners at sunset, reef by morning and Duval Street in between.