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 206 days between Jun 6, 2019 & Dec 31, 2019 View Schedule
Jun 06
6:30 PM
Jun 07
6:30 PM
Jun 08
6:30 PM
Jun 09
6:30 PM
Jun 10
6:30 PM
Jun 11
6:30 PM
Jun 12
N/A
Sold Out
Jun 13
6:30 PM
Jun 14
N/A
Sold Out
Jun 15
6:30 PM
Jun 16
6:30 PM
Jun 17
6:30 PM
Jun 18
6:30 PM
Jun 19
N/A
Sold Out
Jun 20
6:30 PM
Jun 21
6:30 PM
Jun 22
6:30 PM
Jun 23
6:30 PM
Jun 24
6:30 PM
Jun 25
6:30 PM
>
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 208 days between Jun 6, 2019 & Dec 31, 2019 View Schedule
Jun 06
9:00 AM
1:30 PM
Jun 07
9:00 AM
1:30 PM
Jun 08
9:00 AM
1:30 PM
Jun 09
9:00 AM
Jun 10
9:00 AM
1:30 PM
Jun 11
9:00 AM
1:30 PM
Jun 12
9:00 AM
1:30 PM
Jun 13
N/A
Sold Out
Jun 14
9:00 AM
Jun 15
9:00 AM
1:30 PM
Jun 16
9:00 AM
1:30 PM
Jun 17
9:00 AM
1:30 PM
Jun 18
9:00 AM
1:30 PM
Jun 19
9:00 AM
Jun 20
9:00 AM
1:30 PM
Jun 21
9:00 AM
1:30 PM
Jun 22
9:00 AM
1:30 PM
Jun 23
9:00 AM
1:30 PM
Jun 24
9:00 AM
1:30 PM
Jun 25
9:00 AM
1:30 PM
>
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 208 days between Jun 6, 2019 & Dec 31, 2019 View Schedule
Jun 06
9:00 AM
1:30 PM
Jun 07
9:00 AM
1:30 PM
Jun 08
9:00 AM
1:30 PM
Jun 09
9:00 AM
Jun 10
9:00 AM
1:30 PM
Jun 11
9:00 AM
1:30 PM
Jun 12
9:00 AM
1:30 PM
Jun 13
N/A
Sold Out
Jun 14
9:00 AM
Jun 15
9:00 AM
1:30 PM
Jun 16
9:00 AM
1:30 PM
Jun 17
9:00 AM
1:30 PM
Jun 18
9:00 AM
1:30 PM
Jun 19
9:00 AM
Jun 20
9:00 AM
1:30 PM
Jun 21
9:00 AM
1:30 PM
Jun 22
9:00 AM
1:30 PM
Jun 23
9:00 AM
1:30 PM
Jun 24
9:00 AM
1:30 PM
Jun 25
9:00 AM
1:30 PM
>
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 61 days between Nov 1, 2019 & Dec 31, 2019 View Schedule
Nov 01
6:00 PM
Nov 02
6:00 PM
Nov 03
6:00 PM
Nov 04
6:00 PM
Nov 05
6:00 PM
Nov 06
6:00 PM
Nov 07
6:00 PM
Nov 08
6:00 PM
Nov 09
6:00 PM
Nov 10
6:00 PM
Nov 11
6:00 PM
Nov 12
6:00 PM
Nov 13
6:00 PM
Nov 14
6:00 PM
Nov 15
6:00 PM
Nov 16
6:00 PM
Nov 17
6:00 PM
Nov 18
6:00 PM
Nov 19
6:00 PM
Nov 20
6:00 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 159 days between May 27, 2019 & Nov 2, 2019 View Schedule
May 26
10:00 AM
May 27
10:00 AM
May 28
10:00 AM
May 29
10:00 AM
May 30
10:00 AM
May 31
10:00 AM
Jun 01
10:00 AM
Jun 02
10:00 AM
Jun 03
10:00 AM
Jun 04
10:00 AM
Jun 05
10:00 AM
Jun 06
N/A
Sold Out
Jun 07
10:00 AM
Jun 08
10:00 AM
Jun 09
10:00 AM
Jun 10
10:00 AM
Jun 11
10:00 AM
Jun 12
10:00 AM
Jun 13
10:00 AM
Jun 14
10:00 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 218 days between May 27, 2019 & Dec 31, 2019 View Schedule
May 26
10:00 AM
May 27
10:00 AM
May 28
N/A
Sold Out
May 29
10:00 AM
May 30
10:00 AM
May 31
10:00 AM
Jun 01
10:00 AM
Jun 02
10:00 AM
Jun 03
10:00 AM
Jun 04
10:00 AM
Jun 05
10:00 AM
Jun 06
10:00 AM
Jun 07
10:00 AM
Jun 08
10:00 AM
Jun 09
10:00 AM
Jun 10
10:00 AM
Jun 11
10:00 AM
Jun 12
10:00 AM
Jun 13
10:00 AM
Jun 14
10:00 AM
>
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 38 days between Now & Dec 31, 2019 View Schedule
May 26
11:00 AM
1:30 PM
6:30 PM
May 27
N/A
Sold Out
May 28
N/A
Sold Out
May 29
N/A
Sold Out
May 30
N/A
Sold Out
May 31
N/A
Sold Out
Jun 01
N/A
Sold Out
Jun 02
N/A
Sold Out
Jun 03
N/A
Sold Out
Jun 04
N/A
Sold Out
Jun 05
N/A
Sold Out
Jun 06
N/A
Sold Out
Jun 07
N/A
Sold Out
Jun 08
N/A
Sold Out
Jun 09
N/A
Sold Out
Jun 10
N/A
Sold Out
Jun 11
N/A
Sold Out
Jun 12
N/A
Sold Out
Jun 13
N/A
Sold Out
Jun 14
N/A
Sold Out
>
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 159 days between May 27, 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
>
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