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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About Sunset Sail Key West

Home to Key West's finest schooner sunset sail. Beautiful sunset sailing from downtown Key West and the luxurious Perry Marina.

For the Love of Sailing

‍Sunset Sail Key West is more than just a private sailing charter, it is the culmination of decades of experience and a lifetime of passion for sailing, and for Key West. Our top priority is sharing the joy of boatmanship with our guests. We love making new friends and hopefully inspiring a few new sailors along the way. It is our mission to offer authentic sailing experiences around Key West, away from the crowds and noise of party boats and booze cruises.



Early Days...

Sunset Sail Key West is more than just a private sailing charter, it is the culmination of decades of experience and a lifetime of passion for sailing, and for Key West. Our top priority is sharing the joy of boatmanship with our guests. We love making new friends and hopefully inspiring a few new sailors along the way. It is our mission to offer authentic sailing experiences around Key West, away from the crowds and noise of party boats and booze cruises.

A Charter is Born

Captain Seth spent years sailing professionally throughout the eastern seaboard and Caribbean, across the Atlantic to the coast of Italy, and even through the Panama Canal. In 2010, after purchasing Conch West on a whim and restoring her for a year, he registered her as a charter boat, and Sunset Sail Key West was born. One day, upon spotting the High Tide dry-docked in Key West and close to ruin, he vowed to restore his old friend to her former glory. After a labor of love restoring her from the ground up, she joined the fleet.

The Fleet is Complete

In 2000, the first time Captain Seth laid eyes on When and If, he had an instant crush. Every few years, in one exotic place or another, he would cross paths with the schooner and take note. In June 2013, Captain Seth was hired to Captain When and If, followed by overseeing her meticulous 18-month long restoration. When the opportunity to purchase the historic yacht came up, there was no question. It was a great honor to keep her in America and to share her with the public as a charter. She is the crown jewel in the Sunset Sail fleet.
When and If

When and If

Marrying old-world elegance with racing performance, this classic yacht is steeped in history and brimming with top-of-the-line detail.

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Malabar X

Malabar X

A true classic, this 1930 wooden schooner yacht was built to win the Newport Bermuda races of her time - which she did, smashing records in 1930 and 1932.

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High Tide

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.

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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!