Follow the Mermaid: Key West Speakeasy Cruise Experience

Read the full experience

Step aboard the Schooner America 2.0 for a magical evening with Follow the Mermaid... in Key West, Florida. This unique speakeasy cruise combines the charm of vintage nightlife with captivating live performances including aerial acts and burlesque, all set against the backdrop of the sparkling ocean. Classic Harbor Line’s beautifully restored schooner provides an intimate and atmospheric setting, perfect for those looking to experience something truly different from the usual night out. Sip on expertly crafted cocktails as you take in the colorful sunset and the lively entertainment that keeps the evening buzzing. Whether you’re a nightlife enthusiast or just looking to try something extraordinary during your visit to Key West, this event delivers a memorable blend of elegance and excitement on the water. From the easy-going boat ride along the coast to the high-energy shows, Follow the Mermaid... promises a night full of surprises and delight.

Trip highlights

Difficulty

easy.

Duration

2–3 hours.

Fitness level

No rigorous physical exertion required, suitable for most fitness levels.

Frequently asked questions

Is the cruise suitable for children?

This speakeasy cruise is designed for adults due to the nature of the entertainment and cocktail service.

Are food and drinks included?

The cruise primarily offers cocktails; food options depend on the event, so check with Classic Harbor Line for details.

What is the cancellation policy?

Cancellations require at least 24 hours' notice for a full refund, but check the booking site for the most current terms.

How do I get to the boarding location?

Schooner America 2.0 departs from Key West Historic Seaport, easily accessible via taxi or local transport.

Is there a dress code for the cruise?

Smart casual attire is recommended to match the elegant, festive atmosphere on board.

Are there restroom facilities on the schooner?

Yes, the Schooner America 2.0 is equipped with restroom facilities for guest convenience.

Local insights

Wildlife

You might spot playful bottlenose dolphins near the harbor.
Brown pelicans and white herons are common sights along the shoreline.

History

Key West’s maritime history runs deep; the Schooner America 2.0 continues a legacy of elegant sailing vessels once used for trade and defense.

Conservation

Classic Harbor Line supports sustainable boating practices to protect the fragile marine ecosystem around Key West.

About This Experience

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.

Base locationKey West, Florida

Tours offered24+

Adventure tips

Arrive Early for Best SeatingArriving at least 15 minutes before the cruise ensures you get preferred seating and time to settle in before the show starts.

Dress Smart CasualWear comfortable yet stylish attire suitable for an evening cruise and possible cool breezes off the water.

Motion Sickness PrecautionsIf you tend to get seasick, bring medication or motion sickness bands to enjoy the cruise fully.

Follow Safety InstructionsPay attention to crew safety briefings and instructions to ensure a smooth and secure experience on board.

Recommended gear

Light Jacket or Shawl: Useful to keep warm during cooler evening breezes on the water.
Motion Sickness Relief: Helpful for guests sensitive to boat movement, especially during choppier summer seas.
Comfortable Footwear: Supports easy boarding and movement on the schooner’s deck.
Camera or Smartphone: Capture stunning sunset moments and captivating live performances.