Classic Harbor Line


The Classic Harbor Line provides charter sailing through the emerald seas of Key West, Florida. The boat operates year-round and is a wooden gaff-rigged model, approved for carrying up to 49 passengers. Sailor can catch the boat off of Route 1 in Key West, on William Street. Parking is available on Caroline Street between William and Margaret Streets, just a short walk from the boat. The ticket booth for purchasing your sailing tickets is located at the Schooner Wharf Bar. Guests are treated like VIPs once aboard the ship and enjoy complimentary beverages and a scenic sailing experience. The boat offers a variety of private charters and special event planning is available. Weddings onboard the boat are a truly special experience for the bride, the groom and the guests. There is enough space for a small ceremony and a reception, and the boat is also a poplar location for rehearsal dinners, bachelor and bachelorette parties and after-wedding brunches. The boat has also hosted a variety of corporate team-building events. Businesses enjoy a day on the high seas and engage in educational and competitive team building activities that are hands-on and leave a lasting impression. Previous clients have included JP Morgan, Conde Nast, American Express, Microsoft and Pfizer.

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