Charles T.
11/11/2025
Dan took awesome care of us, and Ray was an amazing Captain. Had the best time ever.
Classic Harbor Line Key West
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202 William St
Key West, FL 33040
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 a memory that lasts forever.
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Reviews
5.0116 reviewsJonathan B.
11/10/2025
Incredible experience on board America 2.0! The Schooner was immaculate, the crew was amazing, reservations & communications were excellent and the sunset views were unbeatable...Had several...
Ray H.
11/16/2025
Nice cruise. Only issues were no on at ticket gate ate time we were told to be there and didn't start boarding until departure time
Lindsay J.
12/9/2024
A really awesome team here. We chartered a private sale for a company event and the whole group was beyond happy with the trip. Captain Tom and the crew were polite, informative and so nice to...
Mike T.
4/13/2025
Beautiful day sailing on the America 2.0. Captain and crew were flawless in sailing the schooner, as well as being great hosts. We enjoyed a wonderful cruise, and will do it again!
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