Do I need to book tickets in advance?

Yes, availability is limited especially for holiday sails, so early booking is highly recommended.

Are children allowed on board?

Yes, all passengers require tickets; children under two are free and under 13 pay a reduced rate.

Is food and drink included?

Complimentary hors d'oeuvres, champagne, wine, beer, soft drinks, and water are provided; cocktails can be purchased separately.

Is the schooner safe if I get seasick?

The America 2.0 is steady and gentle, with safety equipment onboard; light seasickness medication is advisable if you’re sensitive.

Where does the sail depart and return?

Sails depart from and return to the Key West Bight dock at 202R William Street.

Is the boat wheelchair accessible?

No, the Schooner America 2.0 is not wheelchair accessible due to its design.

Experience the Magic of Key West: Christmas Day Sunset Sail Aboard Schooner America 2.0 | Boat Rental | Boat Tour

Set against the vibrant hues of the Florida Keys, Key West offers one of the most visually arresting sunset experiences, and this Christmas Day Sunset Sail aboard the Schooner America 2.0 is an unparalleled way to witness it. Departing from the historic Key West Bight at 202R William Street, this two-hour sailing adventure glides through crystalline turquoise waters, passing iconic sights like Fort Zachary Taylor and the Sand Key Lighthouse. The vessel, a 105-foot reproduction of the famed 1851 schooner, is crafted with teak decks and mahogany trim, blending classic nautical elegance with modern comfort.

What makes the Schooner America 2.0 a standout on Key West’s bustling waterfront is its unique blend of history and design. Built by Scarano Boat Building—the same yard responsible for the original Schooner America famed in New York City—the ship embodies maritime heritage while lounging guests amidst spacious sails covering 3600 square feet. The smooth, steady passage of this 85-passenger vessel makes it an excellent choice even for those new to sailing or worried about seasickness.

This special holiday sail enhances the seasonal spirit with complimentary champagne, wine, beer, soft drinks, and hors d'oeuvres including shrimp cocktail, cheese, and fresh veggies. Guests are invited to capture holiday memories at the helm with a festive photo opportunity. Beyond the sumptuous offerings and comfort, attentive crew members provide a warm and professional atmosphere that elevates the entire experience.

On the horizon, watch for glimpses of dolphins and sea turtles, plus rare waterfowl that frequent these tropical waters. One particularly magical moment to anticipate is the elusive Key West "Green Flash," a brief emerald glow that appears just as the sun dips below the horizon. In addition to the postcard-perfect seascape, this sail provides unparalleled photo opportunities and peaceful moments to soak in the vivid colors reflecting off the waves.

Key West itself is a vibrant island city rich in maritime culture and history, known for its laid-back charm and diverse marine ecosystem. The Classic Harbor Line’s winter presence here—usually from November through May—adds a layer of timeless romance and adventure to the local outdoor scene. Whether you’re celebrating the holidays, marking a special occasion, or just seeking a memorable sunset, this sail captures the essence of the island’s magic.

Highly recommended for couples, families, and small groups, this guided sail balances ease with elegance, making it a unique addition to any Florida Keys itinerary. Remember to dress comfortable and bring a light jacket for the evening sea breeze. With limited availability, early booking secures your spot on this distinctive seasonal voyage that combines nature, history, and festive celebration all in one unforgettable package.

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.