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

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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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 216 days between Jul 29, 2018 & Apr 30, 2019 View Schedule
Jul 29
6:30 PM
Jul 30
6:30 PM
Jul 31
6:30 PM
Aug 01
6:30 PM
Aug 02
6:30 PM
Aug 03
6:30 PM
Aug 04
6:30 PM
Aug 05
6:30 PM
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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 156 days between Jul 29, 2018 & Dec 31, 2018 View Schedule
Jul 29
9:00 AM
1:30 PM
Jul 30
9:00 AM
1:30 PM
Jul 31
9:00 AM
1:30 PM
Aug 01
9:00 AM
9:00 AM
Aug 02
9:00 AM
9:00 AM
Aug 03
9:00 AM
9:00 AM
Aug 04
9:00 AM
9:00 AM
Aug 05
9:00 AM
9:00 AM
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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 156 days between Jul 29, 2018 & Dec 31, 2018 View Schedule
Jul 29
9:00 AM
1:30 PM
Jul 30
9:00 AM
1:30 PM
Jul 31
9:00 AM
1:30 PM
Aug 01
9:00 AM
9:00 AM
Aug 02
9:00 AM
9:00 AM
Aug 03
9:00 AM
9:00 AM
Aug 04
9:00 AM
9:00 AM
Aug 05
9:00 AM
9:00 AM
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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 234 days between Jul 18, 2018 & Mar 9, 2019 View Schedule
Jul 18
10:00 AM
Jul 19
10:00 AM
Jul 20
10:00 AM
Jul 21
10:00 AM
Jul 22
10:00 AM
Jul 23
10:00 AM
Jul 24
10:00 AM
Jul 25
10:00 AM
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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 317 days between Jul 18, 2018 & May 31, 2019 View Schedule
Jul 18
9:00 AM
2:00 PM
Jul 19
9:00 AM
Jul 20
9:00 AM
Jul 21
9:00 AM
2:00 PM
Jul 22
9:00 AM
2:00 PM
Jul 23
9:00 AM
2:00 PM
Jul 24
9:00 AM
2:00 PM
Jul 25
9:00 AM
2:00 PM
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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 183 days between Nov 21, 2018 & May 27, 2019 View Schedule
Nov 21
4:30 PM
Nov 22
4:30 PM
Nov 23
4:30 PM
Nov 24
4:30 PM
Nov 25
4:30 PM
Nov 26
4:30 PM
Nov 27
4:30 PM
Nov 28
4:30 PM
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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 167 days between Jul 18, 2018 & Dec 31, 2018 View Schedule
Jul 18
9:00 AM
11:00 AM
1:00 PM
3:00 PM
Jul 19
9:00 AM
11:00 AM
1:00 PM
3:00 PM
Jul 20
9:00 AM
11:00 AM
1:00 PM
3:00 PM
Jul 21
9:00 AM
11:00 AM
1:00 PM
3:00 PM
Jul 22
9:00 AM
11:00 AM
1:00 PM
3:00 PM
Jul 23
9:00 AM
11:00 AM
1:00 PM
3:00 PM
Jul 24
9:00 AM
11:00 AM
1:00 PM
3:00 PM
Jul 25
9:00 AM
11:00 AM
1:00 PM
3:00 PM
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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 54 days between Now & May 31, 2019 View Schedule
Jul 17
5:30 PM
Jul 18
5:30 PM
Jul 19
5:30 PM
Jul 20
5:30 PM
Jul 21
5:30 PM
Jul 22
5:30 PM
Jul 23
5:30 PM
Jul 24
5:30 PM
>
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