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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(305) 587-4488

Our Promise:
An Exceptional, Intimate Sailing Experience Aboard Our Classic Yachts and Schooners

Our Promise:
An Exceptional, Intimate Sailing Experience Aboard Our Classic Yachts and Schooners

What Our Customers Are Saying

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  • “Crew was great. They were very professional and friendly. Our safety was first priority. The trip was very windy but I never felt unsafe. Great people! ”

    Jamie R

  • “We went out on the High Tide with Harley and Preston, and had a fantastic time! Killer boat, and killer captain and crew. Thanks, guys! !”

    Dru3k

  • “What a stunning boat. We were fortunate enough to have a good wind and a great sail that night. The crew is so friendly and knowledgeable. And we really enjoyed their Schooner wine too!”

    Kelly A.

  • “What a perfect evening! My husband and I were looking for a sunset sail to celebrate on our honeymoon and this was exactly what we were hoping for. The crew was exceptional. We loved getting to know them and their experience. The wine was lovely and free-flowing. We loved getting to know the other guests as well. Leaving from Stock Island was very convenient for us as we were staying at a resort a few minutes away. We didn't want a "booze cruise" but a way to fully enjoy a historic sailboat and some lovely views. This was it! We hope to track down the "When and If" at another port in the near future! Thank you all! "

    Bradley F.

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

For the Love of Sailing

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.

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THREE CLASSIC BOATS

Real. Fun. Sailing.

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.

VIEW OUR FLEET

THREE CLASSIC BOATS

Real. Fun. Sailing.

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.

VIEW OUR FLEET

Connect With Us

@SunsetSailKeyWest


NEWS

Anchored in Key West: News & Musings from Sunset Sail Key West

  • Classic Schooner Blue Angels Viewing Cruise

    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.

  • A proposal to remember at Sunset Sail Key West

    With our selection of coral, pearl and diamond proposal packages we're sure to have everything you need for the perfect moment.

  • Wreckers' Race Season

    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!

  • Check Out Our Ship's Store!

    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.