Is prior sailing experience required?

No prior experience is needed; the crew will guide you through any sailing activities.

Are refreshments provided onboard?

Light snacks and beverages are usually available, but it’s best to confirm when booking.

Can children participate in the sail?

Yes, this tour is family-friendly and suitable for children with adult supervision.

What happens if it rains?

Tours operate rain or shine; light rain is typically fine but heavy storms may lead to rescheduling.

Is the boat wheelchair accessible?

Due to the vessel’s design, wheelchair access is limited. Please contact the company for specific accommodations.

How many guests are on each sail?

Group sizes are kept small for an intimate, private experience with personalized attention.

Classic Day Sail on Schooner America 2.0 in Key West | Boat Tour | Dolphin

Set sail on a captivating 1.5-hour journey aboard the iconic Schooner America 2.0, a 105-foot historic vessel offering a unique glimpse into sailing heritage combined with modern luxury. Departing from Key West, Florida, this private boat tour invites you to experience the thrill of hoisting sails alongside an expert crew while soaking in stunning waterfront views. The chance to spot playful dolphins adds excitement, and onboard narration provides engaging insight into the area’s marine life and rich maritime history. Whether you're a sailing enthusiast or a first-timer, this adventure is perfect for connecting with nature and water in an intimate setting. Key West’s warm breezes and sparkling waters create an ideal backdrop for photography and relaxation. With a limit on guest numbers, each sail feels exclusive, making it a memorable experience for families, couples, or small groups seeking day-long escape on the open water. Classic Harbor Line delivers impeccable service and a safe, comfortable atmosphere to maximize your enjoyment of Florida’s coastal charms.

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.