Do sails sell out frequently?

Yes, sails often sell out. It’s recommended to book early or check availability shortly before your intended date.

Is lunch included on the sail?

Yes, a boxed lunch from Old Town Bakery with a sandwich, chips, and dessert is provided for all guests.

Are alcoholic beverages included?

Adults receive two complimentary drinks of beer, wine, or champagne; additional drinks can be purchased onboard.

Is the Schooner America 2.0 wheelchair accessible?

No, the schooner is not wheelchair accessible due to the vessel’s design and deck layout.

What happens if the weather is bad?

Trips run in light rain but may be canceled in severe weather with options for rescheduling or refunds.

Are there bathrooms on board?

Yes, the schooner has private marine heads accessible at all times during the trip.

Experience the Thrill of the Wreckers Race Aboard Schooner America 2.0 in Key West

Set sail from the lively historic district of Key West, Florida, aboard the famous Schooner America 2.0 for the exhilarating Wreckers Race — a maritime tradition revived from the days when daring locals raced to claim stranded pirate ship cargo on Sand Key Reef. This unique 3-hour adventure offers a rare glimpse into the island’s spirited seafaring history as you race alongside a fleet of schooners towards the iconic Sand Key Lighthouse, located nine miles offshore. The shimmering turquoise waters stretch in every direction under expansive blue skies, framed by striking landmarks such as Mallory Square, Fort Zachary Taylor, and Sunset Pier. Keep your eyes peeled for dolphins surfacing and sea turtles drifting through the waves, adding a lively natural backdrop to this historic contest.

Onboard the Schooner America 2.0, you’ll experience a perfect blend of speed and elegance. Known for its swift yet steady handling, the vessel offers a safe and comfortable ride for guests of nearly all ages. With a friendly crew at the helm, your afternoon will include a delicious boxed lunch curated by local favorites at Old Town Bakery, plus two complimentary rounds of beer, wine, or champagne for adults to toast your seafaring efforts (soft drinks and water are always available). The race itself starts promptly at 1:00 p.m. after the firing of the cannon, an exciting signal that transports visitors back to the golden age of wreckers and pirates.

Key West’s vibrant waterfront comes alive during the Wreckers Race, blending adventure sport with social festivity. Whether you’re a passionate sailor or a curious traveler, this race is one of the most spirited ways to connect with the rich maritime culture of the Florida Keys. Following the race, prizes and accolades are awarded at the Schooner Wharf Bar, allowing for a festive evening to celebrate victories and stories shared on the water.

Accessible from downtown Key West’s William Street, this tour is perfect for visitors based in the city looking for a moderate activity that balances excitement with comfort. The Wreckers Race aboard Schooner America 2.0 stands out as a must-do for anyone seeking a hands-on sailing experience steeped in local lore, spectacular ocean scenery, and a taste of Key West’s spirited heritage.

About Classic Harbor Line - Key West

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.