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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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 160 days between May 26, 2019 & Nov 2, 2019 View Schedule
May 26
5:30 PM
May 27
5:30 PM
May 28
5:30 PM
May 29
5:30 PM
May 30
5:30 PM
May 31
5:30 PM
Jun 01
5:30 PM
Jun 02
5:30 PM
Jun 03
5:30 PM
Jun 04
5:30 PM
Jun 05
5:30 PM
Jun 06
5:30 PM
Jun 07
5:30 PM
Jun 08
5:30 PM
Jun 09
5:30 PM
Jun 10
5:30 PM
Jun 11
5:30 PM
Jun 12
5:30 PM
Jun 13
5:30 PM
Jun 14
5:30 PM
>
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 166 days between Now & Dec 31, 2019 View Schedule
Jan 19
11:00 AM
1:30 PM
4:30 PM
Jan 20
11:00 AM
1:30 PM
4:30 PM
Jan 21
11:00 AM
1:30 PM
4:30 PM
Jan 22
11:00 AM
1:30 PM
4:30 PM
Jan 23
11:00 AM
1:30 PM
4:30 PM
Jan 24
11:00 AM
1:30 PM
4:30 PM
Jan 25
11:00 AM
1:30 PM
4:30 PM
Jan 26
11:00 AM
1:30 PM
4:30 PM
Jan 27
4:30 PM
Jan 28
11:00 AM
1:30 PM
4:30 PM
Jan 29
11:00 AM
1:30 PM
4:30 PM
Jan 30
11:00 AM
1:30 PM
4:30 PM
Jan 31
11:00 AM
1:30 PM
4:30 PM
Feb 01
11:00 AM
1:30 PM
4:30 PM
Feb 02
11:00 AM
1:30 PM
4:30 PM
Feb 03
11:00 AM
1:30 PM
4:30 PM
Feb 04
11:00 AM
1:30 PM
5:00 PM
Feb 05
11:00 AM
1:30 PM
5:00 PM
Feb 06
11:00 AM
1:30 PM
5:00 PM
Feb 07
11:00 AM
1:30 PM
5:00 PM
>
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 331 days between Jan 30, 2019 & Dec 31, 2019 View Schedule
Jan 30
4:30 PM
Jan 31
4:30 PM
Feb 01
5:00 PM
Feb 02
5:00 PM
Feb 03
5:00 PM
Feb 04
5:00 PM
Feb 05
5:00 PM
Feb 06
5:00 PM
Feb 07
5:00 PM
Feb 08
N/A
Sold Out
Feb 09
5:00 PM
Feb 10
5:00 PM
Feb 11
5:00 PM
Feb 12
5:00 PM
Feb 13
5:00 PM
Feb 14
5:00 PM
Feb 15
5:00 PM
Feb 16
5:00 PM
Feb 17
N/A
Sold Out
Feb 18
5:00 PM
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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 332 days between Jan 30, 2019 & Dec 31, 2019 View Schedule
Jan 30
11:00 AM
Jan 31
11:00 AM
Feb 01
11:00 AM
Feb 02
11:00 AM
Feb 03
11:00 AM
Feb 04
11:00 AM
Feb 05
11:00 AM
Feb 06
11:00 AM
Feb 07
11:00 AM
Feb 08
N/A
Sold Out
Feb 09
11:00 AM
Feb 10
11:00 AM
Feb 11
11:00 AM
Feb 12
11:00 AM
Feb 13
11:00 AM
Feb 14
11:00 AM
Feb 15
11:00 AM
Feb 16
N/A
Sold Out
Feb 17
N/A
Sold Out
Feb 18
11:00 AM
>
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 332 days between Jan 30, 2019 & Dec 31, 2019 View Schedule
Jan 30
11:00 AM
Jan 31
11:00 AM
Feb 01
11:00 AM
Feb 02
11:00 AM
Feb 03
11:00 AM
Feb 04
11:00 AM
Feb 05
11:00 AM
Feb 06
11:00 AM
Feb 07
11:00 AM
Feb 08
N/A
Sold Out
Feb 09
11:00 AM
Feb 10
11:00 AM
Feb 11
11:00 AM
Feb 12
11:00 AM
Feb 13
11:00 AM
Feb 14
11:00 AM
Feb 15
11:00 AM
Feb 16
N/A
Sold Out
Feb 17
N/A
Sold Out
Feb 18
11:00 AM
>
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 347 days between Now & Dec 31, 2019 View Schedule
Jan 19
2:00 PM
Jan 20
9:00 AM
2:00 PM
Jan 21
9:00 AM
2:00 PM
Jan 22
9:00 AM
2:00 PM
Jan 23
9:00 AM
2:00 PM
Jan 24
9:00 AM
2:00 PM
Jan 25
9:00 AM
2:00 PM
Jan 26
9:00 AM
2:00 PM
Jan 27
9:00 AM
2:00 PM
Jan 28
9:00 AM
2:00 PM
Jan 29
2:00 PM
Jan 30
9:00 AM
2:00 PM
Jan 31
9:00 AM
2:00 PM
Feb 01
9:00 AM
2:00 PM
Feb 02
9:00 AM
2:00 PM
Feb 03
9:00 AM
2:00 PM
Feb 04
9:00 AM
2:00 PM
Feb 05
9:00 AM
2:00 PM
Feb 06
9:00 AM
2:00 PM
Feb 07
9:00 AM
2:00 PM
>
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 287 days between Jan 20, 2019 & Nov 2, 2019 View Schedule
Jan 20
9:30 AM
Jan 21
9:30 AM
Jan 22
9:30 AM
Jan 23
9:30 AM
Jan 24
9:30 AM
Jan 25
9:30 AM
Jan 26
9:30 AM
Jan 27
9:30 AM
Jan 28
9:30 AM
Jan 29
9:30 AM
Jan 30
9:30 AM
Jan 31
9:30 AM
Feb 01
9:30 AM
Feb 02
9:30 AM
Feb 03
9:30 AM
Feb 04
9:30 AM
Feb 05
9:30 AM
Feb 06
9:30 AM
Feb 07
9:30 AM
Feb 08
9:30 AM
>
Enjoying the cruise
This is probably the best sunset cruise I have ever been on because the boat let me bring a few friends for an intimate time to relax and take in the beauty of the sun setting off the Florida Keys.
Pricing and schedule are currently unavailable.
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