Ticketed Cruises

Take to the water and fall in love all over again with Key West. Classic Harbor Line provides unprecedented views of modern-day Key West aboard old-world-style yachts. As designer, builder, and operator of classically inspired boats, our guests enjoy day and sunset Sails of the emerald green waters of Key West aboard finely crafted Schooner America 2.0 featuring teak decks, varnished mahogany rails and gleaming brass fixtures.

Experience the turn of the century of yachting while sailing today's Key West Waters, with breathtaking views of the magical Key West Green Flash. Whether it's non-narrated, lightly narrated or fully narrated, each excursion is its own unfolding story.

Join us for a Day Sail, and sail alongside of the dolphins. Set sail at sunset and enjoy the hospitality of our Captain and Crew. Lighted Boat Parades and Sightseeing Sails will keep you engaged and the Full Moon Sails will be your next date idea. Whatever you choose you are sure to enjoy your time out of the water with us as our crew treats you with the most professional hospitality.

“We booked a Sunset trip on the America 2.0. One word: FANTASTIC. Welcoming & fun crew. Great sailing experience. I felt very safe in their hands. Drinks and snacks provided (and plentiful supply of both). Crew very engaging and answered questions. The sunset was awesome, we had great weather conditions for the sail.”
~ Sunset Cruise Customer