Key West, FL
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Key West Sunset Cruise just got upgraded….

Thank you Key West
November 2024 Season»

Our November 2024 schedule is loaded, grab your tickets now!

Key West Sunset Cruise
Sunset Sail»

Schooner America 2.0 is sailing the emerald green waters of Key West! Step aboard this stunning sailboat, and cruise with us into the magical Key West sunset!

Special Events
Day Sail»

Soak in the sun and join us for an afternoon sail on the emerald green waters of Key West.

Wreckers Race
Sailing Season»

Schooner America 2.0 starts sailing on November 13th! Grab your tickets now!

Key West Full Moon Sails
Key West Full Moon Sail»

Join us for an evening out on the water for a Full Moon Sail on Schooner America 2.0!


Classic Harbor Line: Key West

Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessel in the local Key West fleet: Schooner America 2.0. While visiting Key West, Florida you will find a number of land and water based activities. However, a classic schooner sail, whether it be a day sail, or sunset sail, is well known to be the quintessential Key West activity that will highlight your stay and be the lasting memory forever.

South Florida sightseeing is all about getting on the water, seeing the wildlife, watching the Key West sunset with a loved one, and experiencing the adventure sailing in the great Key West Florida breeze. A 2 hour sailboat ride is a great way to take advantage of your time in Key West to enjoy all of these things.

Whether buying tickets for one of our Champagne Sunset Sails, Afternoon Key West day sail, Full Moon, Star-Gazer Sails; or Privately Chartering the schooners for a special family event or corporate event, you will be amazed by America 2.0’s beauty and comfort. It is maintained by the same creators of Key West’s former pride, Schooner America.

Classic Harbor Line is not only known for operating with amazing sailboats and classic yachts in Boston, New York, Newport, and Key West, but they are also renowned for their outstanding hospitality and customer service. You will find your captain and crew extremely capable, accommodating, helpful, and friendly whether you are spontaneously buying tickets for a classic day sail or planning your one-of-a-kind wedding day.

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