Classic Harbor Line Key West Activities

Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash". Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So take a turn at the helm of one of the fastest schooners in the United States, book today!

Explore the high seas in style on the Schooner America 2.0, namesake of the first sailboat to win the America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights on the beautiful waters around Key West. Book your spot today!