Sunset Watersports is Key West’s Original Watersports Company, established in 1984, family-owned and operated for over 40 years. They offer a wide range of watersports activities including jet ski tours, sandbar charters, reef snorkeling, parasailing, dolphin watching, sunset dinner cruises, private charters, boat rentals, golf cart rentals, and Key West weddings on luxury catamarans for 2 to 149 guests, focusing on safety, fun, exceptional service, and best value.

Classic Harbor Line offers private yacht charters on the 105-ft. Schooner America 2.0 in Key West, guiding guests through emerald green waters for daytime sightseeing sails, magical private sunset cruises, corporate events, birthday parties, weddings, anniversaries, and company outings. The U.S. Coast Guard-certified vessel accommodates up to 85 guests with bar and catering options, located in historic Old Town Key West.

Located in Key West, Florida, the Schooner Spirit of Independence offers an authentic sailing experience steeped in history and tradition. Family owned and operated since 1972, this vessel is known for its meticulous attention to detail and adaptive sailing techniques that respond to the wind and weather conditions of the day. The schooner sails from Schooner Wharf and navigates various scenic routes including the Key West beach, the calm waters of the North West Passage, and Key West harbor. The crew, led by Captain Ricky with over five decades of sailing experience, brings a wealth of knowledge and passion to each voyage, making every trip aboard the Spirit of Independence unique and memorable. The schooner provides a range of activities including sunset sails, private charters, and wedding ceremonies, catering to both casual tourists and special event clients. It also has a strong educational component, having taught seamanship to thousands of scouts and offering adventurous voyages that include snorkeling and maritime rescue experiences. The crew comprises licensed captains and specialists such as an onboard marine biologist, ensuring a safe, informative, and enjoyable journey. Whether guests seek a romantic sunset cruise, a memorable wedding setting, or an educational sailing adventure, the Spirit of Independence delivers an immersive and authentic Key West maritime experience.