Discover Your Perfect Private Charter
Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.
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Your one stop shop for all our awesome swag. Take a look at our selection of hats, tee shirts and other commemorative items, and have them delivered right to your door.
SHOP NOWABOUT US
Sunset Sail Key West is more than just a private sailing charter — it's the culmination of decades of experience and a lifelong passion for sailing and the unique spirit of 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. Our mission is to offer authentic sailing experiences, away from the crowds and chaos of party boats and booze cruises. That mission took root early on, around the turn of the century, when a boy named Seth discovered his love for the sea. Working mornings on boats before school, crewing at just 14 years old, and crossing the Atlantic by 17, Seth became the youngest schooner captain in North America by the age of 19.
Captain Seth spent years sailing professionally through the Caribbean, across the Atlantic, and through the Panama Canal before founding Sunset Sail Key West in 2010. After restoring Conch West and launching her as a charter boat, he later found and rebuilt High Tide, a schooner from his youth. The fleet continued to grow when he crossed paths once more with the historic schooner When and If — a vessel he had long admired. After captaining and overseeing her meticulous 18-month restoration, he eventually purchased her, keeping her legacy alive in American waters. Today, she stands as the crown jewel of the Sunset Sail fleet — a symbol of passion, craftsmanship, and a life devoted to the sea.
THREE CLASSIC BOATS
From the old-world elegance of a historic schooner to off-the-beaten-path day trips aboard a nimble sloop, we offer unforgettable glimpses of the Keys.
We sail a fleet of three vintage sailboats, each with its own unique charm and character. A custom sloop, a classic ketch, and a historic schooner are ready to help you create lasting memories on the crystal-clear waters of Key West. Each vessel is suited to a different kind of experience — so take a moment to get to know the boats that make our adventures truly special.
THREE CLASSIC BOATS
From the old-world elegance of a historic schooner to off-the-beaten-path day trips aboard a nimble sloop, we offer unforgettable glimpses of the Keys.
We sail a fleet of three vintage sailboats, each with its own unique charm and character. A custom sloop, a classic ketch, and a historic schooner are ready to help you create lasting memories on the crystal-clear waters of Key West. Each vessel is suited to a different kind of experience — so take a moment to get to know the boats that make our adventures truly special.
March 29th & 30th: For the best view of the Southernmost Air Spectacular 2025 come admire the pride of America's Navy as the Blue Angels soar overhead. Glimpse the planes through the rigging as they fly above, or enjoy the panoramic view to the horizon from the deck.
With our selection of coral, pearl and diamond proposal packages we're sure to have everything you need for the perfect moment.
Starting the third Sunday in January and every month through April, book your seat on When And If to race a winner to the reef for salvage rights as in the days of Old!
Your one stop shop for all our awesome swag. Take a look at our selection of hats, tee shirts and other commemorative items, and have them delivered right to your door.
Sunset Sail Key West isn’t just a sailing charter — it’s the product of a lifetime spent chasing the horizon. With decades of experience and a deep-rooted passion for sailing and the magic of Key West, each trip is crafted to share that love with every guest. Whether you’re setting out on a shared cruise or a private adventure, it’s more than just a sail — it’s a moment to connect with the sea, the sunset, and something unforgettable.
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