About Sunset Sail Key West

Sunset Sail Key West is more than a charter — it’s the result of a lifetime spent on the water, sharing the magic of sailing and the beauty of Key West with every guest.

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Our Fleet

High Tide

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High Tide

With a large, comfortable cockpit, High Tide is perfect for group fun in the sun– family snorkeling trips to the National Wildlife Preserve, bachelorette parties, lilypad lounging, and visits to the mangrove island bird sanctuary.

If the thought of getting chummy with the captain, learning the ropes, and taking a turn at the wheel floats your boat, High Tide is your gal. A super-fast, nimble sloop with a 12-person capacity, High Tide is one of only two medium-sized sailboats in the Key West able to venture into the backcountry. She is also well-suited for romantic sunset sails and celebrating special occasions such as proposals or anniversaries.

Like so many things we love, High Tide is a child of the ‘80s. A Key West, original, she was built locally by the legendary Admiral Finbar for day sailing and snorkeling trips. In 1980, this 33-foot Glander– the first charter sailboat in Key West– lifted anchor and has been bringing the joy of sailing to guests ever since. Captain Seth first sailed on High Tide over 20 years ago. He considers her a trusty, old friend and hopes you will, too.

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TESTIMONIALS

What Customers are Saying

Captain Andy, and crewmen Zach and Dalton were extremely professional, knowledgeable, and kind. We had a beautiful sail and awesome sunset. We will Sali again next time we are in Key West.

First time ever on a sailboat for my whole family, none of us are drinkers so it was really nice to have the Conch West to ourselves. They offered music but we preferred the stillness of the night sailing. It was a beautiful quiet evening and Joe and Chris were very accommodating. We loved the experience and will certainly recommend them to our friends.

Had a lovely time out on the water off the historic Key West port, aboard the 33 foot High Tide. Harley and Casey were wonderful hosts, and were very knowledgable about the local waters. We were provided with plenty of ice, water, and soft drinks during our sunset sail, and thoroughly enjoyed our time under sail. The cheese platter was a nice little nosh while taking in the scenery. Thanks again for all your skill and hospitality!

If you are traveling to Key West and even thinking about doing a Sunset Cruise 100% you should call Sunset Sail Key West... Seth and his crew are amazing. Forget all the corporate charters in town..... sailing in a 1930s era schooner while watching the sunset is the highlight of all my trips to Key West. Well worth the value and the little extra time to drive the couple miles to Stock Island.

We booked a private charter for 7. Our captain was Harley. He was very friendly, and a talented sailor. We went for a 90 minute trip with full sails. He delivered to every request and had a first mate that joined the conversation and was very entertaining. We sail every time we go to the keys and will definitely do this tour again. HIGHLY RECOMMENDED.

This was a great sunset sail with a friendly and capable crew on an absolutely beautiful historic Schooner! We are so glad we went and will do so again.

We booked a private snorkel tour and it was worth every dime. Sailing was very cool, probably the most fun part of the tour! Harley and Casey were very knowledgeable, safe, and fun to be with. The snorkeling was very cool - we saw some spiny lobsters, crab, lots of fish and sponges. Highly recommend, this was a super fun morning!