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“The crew were friendly and on top of filling our drinks. The music was good and he took requests. Our experience was great.”
Experience Key West’s vibrant coral reef on a 3-hour snorkel sailing trip with professional guides, unlimited drinks, and friendly, knowledgeable crew.
“Captain Brett and his crew made the experience amazing. They were very safety minded while also creating a fantastic experience for everyone on board. If you are booking a trip with them don’t forget your sunscreen, and prepare yourself for an amazing trip!”
Experience a cozy sunset sail off Key West with wine, beer, and gourmet snacks. Perfect for relaxed travelers seeking scenic views and quality drinks.
“Quality sail on schooner with wine tasting and small plates. Paired well with fun staff. 5 stars all the way.”
Experience a vibrant sunset cruise in Key West with live music, unlimited drinks, and appetizers—perfect for relaxing and meeting new friends.
“Go with a happy group of people who kmows how to have fun.. qear smiles and dance to the music and meet new people.”
Experience a tranquil sunset from a small sailboat off Key West, with drinks included, attentive crew, and stunning water views—ideal for relaxed evenings.
“Amazing! Eric and Carlos are incredible hosts. The sunset was incredible! And seeing dolphins was an added bonus.”
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.
“great time and great crew. what fun. ffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffff”
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.
“The day was perfect and the crew made sure we had the best time! Thank Brian, James and Connor we will be back!”
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.
“The boat was comfy, the captain is fun and played great music. The wine and tapas were ok. No dolphins anywhere, but the cruise was fun anyway. Gorgeous view of the beautiful sunset!”
Experience Key West’s stunning sunset from a luxurious 69-ft catamaran, enjoying included wine, champagne, and scenic views in a relaxed, authentic setting.
“The crew was incredible. The views and especially the sunset. Celebration for our 30th wedding anniversary. Would recommend this group to all family and friends”
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.
“It was a great tour. We were worried about the weather, but the captain decided to go on the Thanksgiving day with only 5 people on the boat. Very appreciate the decision! The staff was so nice and provided the best service and help us…”
Discover the beauty of Dry Tortugas with this full-day catamaran trip from Key West, featuring snorkeling, historic tours, and stunning ocean views.
“snorkeling was wonderful It was very hot so the water was amazing. Dry Tortegas was ok. Something I would only want to do once.”
Experience soaring above Key West’s turquoise waters with a safe, fun parasailing trip—breathtaking views, friendly staff, and photos to remember.
“Crew and staff are so kind for waiting for us. We are almost late. And also checking us if we are already in the site. Thank you.”
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.
“Fantastic experience, the captain and the crew are fantastic and professional. We will do again for sure”
Experience a stunning Key West sunset on a graceful schooner, enjoy drinks, hors d'oeuvres, and wildlife sightings—all in 2 relaxing hours.
“Such a beautiful sunset cruise! The crew was incredibly friendly and knowledgeable, which made the whole experience even better. The sail was the perfect length — long enough to truly enjoy being out on the water, but not so long that you felt restless. They…”
Experience stunning Key West sunsets with lively music, unlimited open bar, and delicious appetizers on this 2-hour catamaran cruise for $79.95.
“It was a great experience! The sunset was beautiful. Great music and drinks were great too! Not too crowded so plenty of room for everyone to enjoy. We enjoyed it!”
Schooners at sunset, reef by morning and Duval Street in between.