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.
Explore Key West
Join us aboard our historic schooners ! Whether you choose the Schooner Day Sail for a relaxing day at sea or the Classic Schooner Sunset Sail to watch the sun dip below the horizon, each journey offers the perfect way to enjoy the stunning waters of Key West.
ABOUT US
Sunset Sail Key West offers authentic sailing experiences, born from Captain Seth's decades of passion for the sea and his commitment to sharing the joy of boatmanship. Starting his journey at 14, Seth became the youngest schooner captain in North America by 19 and spent years sailing across the Caribbean, the Atlantic, and through the Panama Canal. In 2010, he founded Sunset Sail Key West, restoring boats like Conch West and High Tide before acquiring and restoring the historic schooner When and If. Today, this vessel stands as the crown jewel of the fleet, symbolizing a life dedicated to sailing and craftsmanship.
Book NowTHREE 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.