Do sails sell out frequently?

Yes, these popular night sails often sell out quickly. Booking early is strongly recommended.

Is parking available nearby?

Parking in Key West is limited, but several municipal lots exist near the departure point; detailed info is provided after booking.

Can I bring my own alcoholic beverages?

No, outside alcohol is prohibited by law, but alcoholic drinks can be purchased on board or during booking.

Is the schooner wheelchair accessible?

No, the America 2.0 does not accommodate wheelchairs due to its design.

Are there restrooms on board?

Yes, two marine restrooms are accessible below deck throughout the sail.

Can I book a private charter or wedding?

Yes, private charters and onboard marriage ceremonies are available—contact the operator directly for arrangements.

Experience the Magic of Live Jazz Night Sailing in Key West Harbor | Sailing | Boat Tour

Set against the shimmering waters of Key West Harbor, the Live Jazz Night Sail aboard the Schooner America 2.0 offers an unforgettable blend of maritime charm and soulful music. This 105-foot schooner delivers a unique nighttime sailing experience in the heart of Key West, Florida, where gentle sea breezes and the city's glowing skyline create a captivating backdrop. Guests embark from 202R William Street in historic downtown Key West, a vibrant hub known for its rich maritime history and island culture.

The 1.5-hour cruise features live jazz performances from vocalist Claire Kaplan and guitarist Izzy Zaidman, whose smooth renditions of both jazz standards and contemporary tunes create an inviting atmosphere perfect for couples, friends, or co-workers seeking a relaxed yet lively evening on the water. As the schooner glides through calm waters, passengers enjoy two complimentary beverages from the late-night menu, alongside optional light snacks available for purchase.

What sets this cruise apart is the seamless fusion of sailing and live music on a classic vessel celebrated for its speed and elegance. The America 2.0 is a nod to Key West’s nautical heritage, embodying both the city’s historic charm and its vibrant maritime present. With assigned seating and a comfortable layout, the schooner provides an intimate setting that encourages immersion in the jazz vibe while taking in panoramic views of the harbor’s glowing landmarks.

The night sail is also notably accessible, with stable, gentle sailing that minimizes seasickness risk, making it ideal even for first-time sailors. The onboard crew includes the Captain and two experienced members who ensure safety and comfort, maintaining an inviting, hospitable environment throughout the evening. Marine heads (restrooms) are available below deck, enhancing convenience without compromising the boat’s classic aesthetic.

Key West itself is a distinctive destination, its mix of tropical flora, historic architecture, and warm ocean waters drawing visitors year-round. As the southernmost city in the continental U.S., it offers a blend of cultural influences that perfectly suit the live jazz ambiance—a musical style deeply rooted in American history. The America 2.0’s night sail is a standout local offering, reflecting the city’s laid-back sophistication and celebration of artistic expression.

Whether you’re celebrating a special occasion or simply seeking a different kind of evening out, this live jazz night sail invites you to savor Key West’s nocturnal beauty from an elegant vessel, complete with the soulful soundtrack of expertly performed jazz. It’s a rare chance to connect with the sea, the music, and the spirit of one of Florida’s most beloved coastal towns in a single, memorable outing.

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.