Classic Harbor Line Key West, Florida
Classic Harbor Line proudly runs Schooner America 2.0, the premier sailing vessel in Key West, featuring two-hour sunset and day sails. Complimentary drinks and hors d'oeuvres provided.


Schooner America 2.0 is a 105' vessel built in Albany, New York in 2011. She sails out of Chelsea Piers in New York City from May to October, and then makes her way down the coast to reside in Key West for the winter months where she takes guests out sailing into the beautiful green waters surrounding the island.


Our trip plan is very much dependent on the wind direction for any given day. However, we usually begin our trip with a short sprint up Man O' War Harbor. Then, we'll make a turn and head past Mallory Square and Sunset Pier before making our way out the Main Shipping Channel into open water. Every day we try to get a little closer to Cuba!

Map & Directions

202R William Street, Key West, Florida 33040

Points of Interest
Classic Harbor Line
202R William Street, Key West, Florida

Age range, type of group

We welcome all age groups, families, couples, first dates, and even the occasional solo sailor!

Sleeping and meals

The Schooner America 2.0 does not currently offer any overnight trips. Food and beverages are provided on our sails.

Policies & Restrictions

We allow pets on a situational basis, depending on how many other people will be on the boat. No smoking is allowed as the boat is made of wood.


Classic Harbor Line

Listing # RA-1280719

Starting at:
USD $55 per trip
Reservations & Information
Email this advertiser to make your reservations or get more information.

Travel Dates

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