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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5.0113 reviews
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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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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...

Becky B.
4/11/2025

From the start this excursion was fantastic. Heather and Ray answered questions. Was very accommodating and had lots of great photos. Highly recommend!!

Maria J.
6/3/2025

Thank you so much for a wonderful experience!! The ship is beautiful and clean. The staff were knowledgeable , friendly and very good at their job. Plus it was very safe. It was the best way to...

Charley S.
3/6/2025

Quiet, plenty of room, great sailing. Chelsey and Rae were so efficient that htey made the hard work look easy. Very informative and engaging. Professiomals, really. Day sail is a great deal.

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