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Step aboard the 105-foot Schooner America 2.0 for a private 1.5-hour sail around Key West’s turquoise waters. Enjoy iconic sights like Fort Zachary Taylor and Sand Key Reef with expert crew hospitality ensuring a smooth, memorable voyage.
Step aboard the 105-foot Schooner America 2.0 for a private 1.5-hour sail around Key West’s turquoise waters. Enjoy iconic sights like Fort Zachary Taylor and Sand Key Reef with expert crew hospitality ensuring a smooth, memorable voyage.
Book with Classic Harbor Line - Key West
Verified experiences and guided adventures in the surrounding area.
Operated by Classic Harbor Line - Key West · Key West, Florida
Experience the shimmering turquoise waters and sun-soaked skies of Key West, Florida, aboard the legendary Schooner America 2.0. Docked at 202 William Street, this 105-foot revival schooner, a modern homage to the historic 1851 racing vessel, offers an exclusive private charter sail that epitomizes maritime elegance paired with laid-back tropical charm. Perfectly situated in the southernmost point of the continental U.S., Key West is famed for its vibrant marine life and historic seafaring heritage, making this sail a definitive way to explore its coastal beauty.
The private charter spans about 1.5 hours, where up to 12 guests can unwind on this beautifully maintained vessel designed by Scarano Boat Building—the same craftsmen behind several iconic Classic Harbor Line yachts. As your schooner glides smoothly across the crystalline waters, you’ll catch waterfront views of Fort Zachary Taylor, the coral reefs surrounding Sand Key, and bustling spots like Mallory Square and Sunset Pier framed by the endless blue horizon.
What sets this experience apart is the blend of classic nautical design with impeccable service. The crew, known for their warm hospitality, manage every detail so guests can relax without worrying about logistics. Soda and water come included, with an on-board menu offering alcoholic beverages and snacks for purchase, carefully curated so you can toast to the sea without the hassle of bringing your own drinks. The vessel is equipped with private marine heads (restrooms) below deck, blankets, pillows, and life jackets, ensuring comfort and safety for everyone aboard.
While swimming or snorkeling aren’t part of this charter due to licensing limitations, the real joy comes from the serene sailing itself—the schooner’s historic lines slicing through calm, emerald waters, wildlife sightings including dolphins and pelicans, and the gentle pulse of the sea breeze. Whether you choose a morning departure to savor the sunrise over the waves or an afternoon sail to catch the soft golden light, this trip offers an intimate connection to Key West’s coastal spirit.
Locals and travelers alike cherish Classic Harbor Line for bringing refined, authentic sailing to this island town during the winter months (November through April). Their vessels are a standout presence in the Key West harbor, symbolizing a blend of history, craftsmanship, and signature hospitality that locals proudly support. Whether planning a romantic outing, a family gathering, or an unforgettable group experience, the Schooner America 2.0 private charter offers something distinctly memorable—a leisurely step back into the golden age of sail, framed by the unparalleled beauty of Key West’s seascape.
Yes. All passengers require tickets regardless of age. Children aged 3 and under ride free but still require a free infant ticket.
No outside alcoholic beverages are permitted, but you can purchase drinks on the schooner during your sail.
Yes, the schooner is equipped with private marine heads accessible at all times.
Sails operate in light rain but may be canceled due to severe or unsafe weather. In such cases, full refunds or rescheduling options are offered.
A 15% gratuity is automatically added during booking.
No, unfortunately, the vessel is not wheelchair accessible.
Classic Harbor Line - Key West operates signature sailing experiences aboard the historic Schooner America 2.0, departing from Key West, Florida. The company offers a curated calendar of public and ticketed events including holiday brunches, sunset sails, live-music cruises, themed speakeasy nights, maritime ghost-story evenings, special viewing parties, and seasonal celebrations. Guests can choose from experiences such as Christmas Day Brunch, Mother's Day Mimosa sail, Cocoa and Carols, Haunted Seas narrated by an expert from Haunted Key West, Blue Angels air show viewing, Live Jazz Night, Valentine's Day Champagne sunset, and an intimate New Year’s Eve Dockside Bash limited to forty tickets. Voyages combine scenic cruising through turquoise waters with onboard hospitality: buffet brunches with mimosas, gourmet lunches, complimentary drinks, hors d'oeuvres, and curated desserts. The Schooner America 2.0 features teak and mahogany finishes and provides panoramic views of Key West landmarks, marine wildlife, and sunset phenomena like the “Green Flash.” Special events include VIP dockside access to local traditions and exclusive catering or open-bar options. Safety and guest experience are prioritized through experienced crew members familiar with local waters. Partnerships with local performers and specialists—such as Haunted Key West for ghost storytelling—add authentic, regionally rooted programming. Whether booking a family-friendly holiday cruise, a romantic sunset sail, or a seasonal themed event, Classic Harbor Line - Key West presents reliably produced, limited-capacity sailing experiences that showcase Key West maritime scenery and festive atmosphere. Bookings are available online and through local ticket outlets during peak season, special events, and year-round daily.
Book with Classic Harbor Line - Key West