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

Category Photo
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!
Sort By:

Key West and Florida Keys Sailing Cruises

Search:
View By Date:
Arrival Date:
 
Length of Visit:
View By Date:
Arrival Date:
 
Length of Visit:
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 269 days between Apr 4, 2019 & Dec 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 272 days between Apr 4, 2019 & Dec 31, 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 272 days between Apr 4, 2019 & Dec 31, 2019 View Schedule
The Schooner America 2.0
Enjoy a relaxing sightseeing tour in Key West while on aboard a Schooner and get views of the crystal blue ocean while you see notable sights like the Sand Key Lighthouse when you book the Classic Day Sail Aboard Schooner America 2.0.
Available 36 days between Mar 27, 2019 & May 15, 2019 View Schedule
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.
Available 68 days between Mar 25, 2019 & Dec 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 222 days between Mar 25, 2019 & Nov 2, 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 279 days between Mar 25, 2019 & Dec 31, 2019 View Schedule
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 101 days between Mar 25, 2019 & Dec 31, 2019 View Schedule
Try searching by keyword or choose a specific date.
Search:
View By Date:
Arrival Date:
 
Length of Visit:
View By Date:
Arrival Date:
 
Length of Visit:
Previous Page
1  2 
Next Page
[Next Page]
[Prev Page]
1  2 
Checkout
Cart
Contact Customer Service at
800-987-9852
Secure Online Payment Options
credit card logos