Best Key West Schooner Sailing Tours

Experience a true piece of maritime tradition with Schooner Appledore, the name of a series of two-masted schooners hand-built by Herbert and Doris Smith. Known for circumnavigating the globe, the Smiths named the schooners after Doris’ hometown of Appledore Island.

Originating in the 17th century, schooners were known for their speed, ease in handling, and shallow draft. Whether embarking on a sunset sail or joining in the annual Wrecker’s Cup, a trip on a Schooner Appledore is a perfect way to experience Key West.

Exceptional Schooner Sailing Tours

Schooner Champagne Sunset Sail

STARTS AT $109.95

Key West’s best schooner sail

A sunset sail past local Key West landmarks
The chef’s selection of hors d’oeuvres and cocktail shrimp
Liquor bar, including champagne, sangria, boutique wine, premium beer, cocktails, soft drinks, and filtered water

Bugeye Backcountry Eco-Tour

STARTS AT $119.95

Explore Key West’s diverse ecosystem

Guided snorkeling at patch reefs
A kayaking tour of a mangrove island
Full buffet lunch with bottomless soft drinks, homemade sangria, premium beer, and boutique wine

Why Choose Us

Dive into an underwater paradise with Sebago Watersports. Our tours offer a unique opportunity to explore the beauty that is Key West.
Discover Pristine Reefs & Beaches

Sebago’s experienced captains navigate to different locations based on the day’s weather so you can see the best of Key West’s natural wonder.

Explore with Small Groups

We pride ourselves on limiting passenger numbers, which we find provides ample space for guests to relax in the sun or shade onboard.

Embark On An Authentic Sailing Experience

As our boats enter open Key West waters, each captain unfurls the sails so guests can experience authentic sailing before reaching their snorkel destinations.

Get Comprehensive Safety Training

For each tour, our professional crew provides a thorough safety briefing and instruction in snorkeling. Whether you’re a seasoned snorkeler or trying it for the first time, we’ve got you covered.

Access All-Inclusive Gear and Amenities

Our all-inclusive approach to each tour means that you can set out on your adventure without any worries. From top-notch gear to refreshing beverages, Sebago provides everything you need for a perfect day at sea.

Encounter Marine Wildlife

The Florida Keys Reef is home to a bustling hub of marine biodiversity. With Sebago, you’ll have the chance to see hundreds of species of fish, coral, and other marine wildlife up close in their natural habitat.

Sail In History

“Appledore” is the name of a series of 2-masted schooners hand-built by Herbert and Doris Smith. Named for Doris’ hometown of Appledore Island, off the coast of New England, the Smiths have written two books about their adventures circumnavigating the globe: Dreams of Natural Places and Sailing Three Oceans.

Sebago is proud to have two Appledores in our fleet. And Key West is the best place for sailing a schooner yacht in America. Sailing aboard a tall ship in our calm, turquoise waters provides our guests with a maritime experience unlike any other. Choose from a romantic Key West sunset sail; an afternoon sail; or a backcountry, all-day schooner adventure.

If you’re looking for a truly unique Key West sailing experience, join us for Key West’s annual Wrecker’s Cup. This regatta series is held the last Sunday of January, February, March, and April and re-enacts days gone by when ships raced to grounded wrecks on the shallow waters’ treacherous reefs. Salvage rights were awarded to the first captain to reach a stranded ship and made Key West one of America’s richest cities.

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Wreckers Race at sea with Sebago Watersports while enjoying a scenic view
Wreckers Race at sea with Sebago Watersports while enjoying a scenic view

Meet our schooners

The first, Appledore II, is the largest of the five Appledore Schooners and is considered a prime example of a traditional wooden schooner. She divides her time between Camden, Maine in the Summer and Key West, Florida in the Winter, sailing the 2,000 miles between the ports twice a year.

The second is Appledore Star. Originally christened the “Jenny Norman,” she was built in 1982 by legendary shipwright, Jim Richardson of Lloyds, Maryland. He wanted a boat that was easy to sail but with a historical design, and decided on a wooden two-masted bugeye schooner with a round stern. Jim spent his retirement years sailing the Jenny Norman on the Chesapeake Bay. Now that the wooden bugeye schooner calls Key West home, she was renamed in keeping with the Appledore tradition. “Appledore Star” is derived from two of the islands that make up the Isle of Shoals straddling the Maine-New Hampshire border. Appledore is the largest of these islands in Maine and Star Island is the largest in New Hampshire. With her shallow draft, the Appledore Star is well-suited to exploring Key West’s shallow waters and is the only bugeye schooner in Key West.

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Ready for a little history?

Schooners originated in Europe in the 17th century. Typically, these tall ships carried two masts, but could carry up to seven. In the 18th century, schooners became popular in America for their speed, ease of handling, and shallow draft. In the 19th century, as many as 2,000 schooners plied their trades on the Great Lakes. With the advent of engines, these exquisite ships faded from sight. Until the Smiths revived this glorious era of sailing.

Bugeye schooners were originally designed in the late 1800s for oyster dragging in Maryland’s Chesapeake Bay. Needing a shallow boat, log canoes were the first vessels used for oyster dredging, but proved too small. A centerboard design allowed the bugeye to sail in the bay’s shallow waters while a low bulwark made it easy to handle dredges and drag for oysters. As the oyster harvest declined, the bugeye schooner dropped out of favor and was replaced by the skipjack, a less expensive oyster dragging boat. The Jenny Norman, now our Appledore Star, is the last known bugeye schooner ever built.


Discover what our delighted customer have to say about their extraordinary experiences. Read the reviews to find genuine, glowing testimonials and five star ratings that showcase the excellence of our service, products, and overall customer satisfaction.

Private Charter Requests

Discover Key West your way! Enter your information below and we will be in touch!

Custom Charter Options

  • Experience amazing Key West Sunsets with customized catering options
  • Morning or Afternoon Snorkels
  • All day adventures or eco-tours
  • Dolphin Watches
  • Parasailing


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