About Classic Harbor Line Key West
Classic Harbor Line Key West operates the iconic Schooner America 2.0, a 105-foot replica of the legendary 19th-century racing yacht that inspired the America's Cup. Docked at the Historic Seaport behind Schooner Wharf Bar on William Street, this beautifully restored tall ship offers some of the most elegant sailing experiences in the Florida Keys.
Their lineup includes daytime sightseeing sails, signature sunset cruises, stargazing night sails, and private charters for special events. Each trip includes complimentary beer, wine, champagne, and soft drinks served by a professional crew. The spacious teak decks offer plenty of room to stretch out, and the open-air design gives passengers unobstructed views of Key West's harbour, Fort Zachary Taylor, and the famous Mallory Square sunset.
Classic Harbor Line is a nationally recognized sailing company with fleets in New York and Boston as well, but their Key West operation aboard the America 2.0 is arguably the most scenic. The combination of a historic vessel, professional hospitality, and Key West's spectacular waterfront makes this one of the top-rated sailing experiences in the Florida Keys.
