Key West & Florida Keys, Florida Sightseeing Tours & Cruises – Sailing Cruises

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Head out to the high seas for a sailing adventure with one of our exciting sailing cruises. A cruise like the Schooner Appledore Sail will give you the relaxing experience of a sailing cruise as well as the fun and adventure of heading out into the open waters. Make your reservations today!
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Key West and Florida Keys Sailing Cruises

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Schooner Appledore Key West Cruise
Sailing cruises are an obvious way to have a great time in the waters of the Florida Keys, but there's no experience that compares to the unique charm of the Appledore II, a wonderful schooner that's perfect for sea touring.
Available 187 days between Nov 21, 2018 & May 27, 2019 View Schedule
The Key West sailing cruise around the harbor is a really neat way to see the beautiful homes, the sharp boats, the amazing wildlife, and of course the beautiful colored waters of the area.
Available 314 days between Oct 22, 2018 & Aug 31, 2019 View Schedule
Sunset
See the last living North American Reef in the Florida Keys by sailing on a catamaran through the stunning emerald waters of Key West. See all sorts of aquatic life as you snorkel through the crystal clear waters, then it's off on a sunset sail of the Keys while you enjoy a drink with friends.
Available 98 days between May 26, 2019 & Aug 31, 2019 View Schedule
Sunset from the boat
Enjoy a glass or two of champagne and a few snacks on a sunset cruise, viewing the brilliant colors of the water and spending time with a small group of passengers.
Available 123 days between Nov 1, 2018 & Mar 9, 2019 View Schedule
A Key West Shore Excursion: Shipwreck Snorkel and Wild Dolphin Encounter is a catamaran ride to watch dolphins go about their daily lives and, conditions permitting, to snorkel around a coral reef that formed on the wreckage of a ship.
Available 296 days between Nov 1, 2018 & Aug 31, 2019 View Schedule
Shipwreck Snorkel and Wild Dolphin Encounter
You can enjoy clear, blue waters while partaking in the Key West Shipwreck Snorkel and Wild Dolphin Encounter cruise where you can view playful dolphins courting, and feeding along with shallow-water, coral-encrusted shipwreck observing and post-snorkeling with refreshments and snacks.
Available 297 days between Nov 1, 2018 & Aug 31, 2019 View Schedule
Kayaking in the Key West National Wildlife Refuge
Enjoy Key West Wildlife refuge on the Java Cat Sail, Kayak, and Snorkel Charter where you get to paddle on your kayak through the Lakes Region passing the mangrove islands and seagrass beds, getting to touch actual jellyfish, crabs, after kayaking receive snorkeling instructions, after all that finish off with a light lunch catered.
Available 314 days between Oct 22, 2018 & Aug 31, 2019 View Schedule
Kayaking
I love the ability to do a sailing cruise on a 65 foot schooner with knowledgeable guides that tell us about the history of the area as we sail to the refuge to go kayaking and snorkeling in the waters.
Available 312 days between Oct 22, 2018 & Aug 31, 2019 View Schedule
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