Key West: Live Christmas Holiday Music Cruise with Hot Cocoa

Imagine celebrating the festive season on a charming schooner, with holiday lights twinkling around you and your favorite Christmas tunes playing live. That’s exactly what you get with the Key West Christmas Holiday Music Cruise aboard Schooner America 2.0. This 1.5-hour sail offers a joyful mix of music, holiday decor, and some well-deserved relaxation—perfect for those looking to add a touch of holiday magic to their trip.

One of the standout features we love is the live band that fills the air with cheerful Christmas classics—think “Jingle Bells” and “Silent Night”—all while you enjoy the gentle sway of the boat. Plus, the inclusion of two complimentary drinks (beer, wine, or champagne for those over 21) makes this experience feel even more festive. The decorated schooner with holiday lights creates a cozy, cheerful vibe that transports you straight into the holiday spirit.

A potential consideration is that the cruise is relatively short, just 1.5 hours, which might leave some craving more time to soak in the scenery or socialize. Also, as seating may be assigned, it’s good to plan for some unpredictability in where you’ll sit. Nevertheless, this cruise is best suited for families, friends, or couples wanting a fun, relaxed way to celebrate Christmas in Key West without the fuss of larger crowds.

If you’re seeking a memorable, lively holiday experience that combines scenic views with festive cheer—this cruise ticks many boxes. It’s especially ideal for those who enjoy live music, holiday treats, and a cozy boat atmosphere to make special memories.

Key Points

• Festive atmosphere with holiday lights and decorations on a charming schooner.
• Live Christmas music performed by a fun, upbeat band, perfect for singing along.
• Includes two free drinks (beer, wine, or champagne for 21+), adding to the celebratory vibe.
• Holiday treats and cookies are included, making the cruise sweet and festive.
• Short but sweet at 1.5 hours, great for a quick holiday outing.
• Flexible cancellation policy—cancel up to 24 hours in advance for a full refund.

An In-Depth Look at the Christmas Cruise Experience

Setting Sail on Schooner America 2.0

Starting at 202 William Street, directly behind the Schooner Wharf Bar, this cruise offers a cozy, inviting departure point. Once aboard, the ship is decorated with holiday lights, instantly setting a festive tone. The vessel itself, Schooner America 2.0, is a classic style schooner that feels both traditional and charming—perfect for a relaxed holiday cruise.

Guests are welcomed onto the boat, and while seating may be assigned, the layout encourages mingling and enjoying the views. The crew from Classic Harbor Line – Key West ensures everyone feels comfortable and ready for a good time. The boat’s open deck and ample seating allow for excellent viewing of Key West’s shoreline and the city lights, which are particularly charming at this time of year.

The Musical Festivities

The heart of this cruise is the live band playing Christmas favorites, creating a lively, musical backdrop. Reviewers mention that the band is fun and engaging, encouraging sing-alongs that add a communal holiday spirit. You’ll find yourself humming along to classics like “Rudolph” and “Frosty,” making it more than just a cruise—it’s a mini holiday concert on the water.

Guests particularly appreciated how the music added a cheerful atmosphere, making the 1.5 hours fly by. One review quotes, “The band was lively and got everyone involved, turning the cruise into a festive sing-along.”

Festive Decor and Atmosphere

The boat’s holiday lights and decorations are thoughtfully done, creating a cozy, illuminated environment. This setting makes it perfect for holiday photos and creates a warm backdrop for conversations or quiet moments looking out at the scenic shoreline.

Drinks, Treats, and the Holiday Spirit

Included in your ticket are two drinks—beer, wine, or champagne—offered from the bar, which helps elevate the celebration. For those under 21, hot cocoa or other beverages are available, ensuring everyone can partake in the cheer. Reviewers mention how the drinks, combined with holiday cookies and treats, create a comforting holiday vibe.

Additional drinks are available for purchase, giving guests the option to extend their merriment without feeling rushed. The holiday treats come in the form of cookies and sweets, adding a delightful touch to the experience.

What Makes This Cruise Stand Out

• Scenic views combined with holiday decorations make for memorable photos.
• The live band creates an energetic, engaging atmosphere.
• The short duration allows for a festive experience without feeling overwhelming.
• The flexible cancellation policy offers peace of mind, especially during busy holiday times.

Practical Tips for the Cruise

• Arrive at the meeting point early to secure your preferred seating, as seating might be assigned.
• Dress comfortably but warmly; December evenings in Key West can be breezy, especially on the water.
• Bring your ID if you plan to enjoy alcohol, as two drinks are included for 21+ guests.
• Consider this experience if you’re traveling with family or friends who enjoy lively, musical holiday celebrations.

Why This Tour Offers Good Value

At $88 per person, this cruise provides a blend of scenic views, festive entertainment, and holiday treats—all wrapped up in a cozy boat setting. The inclusion of two drinks and holiday snacks enhances the value, making it a relaxed, enjoyable way to celebrate Christmas without extra costs.

Compared to larger, more commercial holiday events, this cruise offers a more intimate, authentic experience—especially appreciated for its friendly staff, engaging music, and scenic backdrop. For travelers seeking a festive, memorable activity that balances fun with relaxation, this cruise hits the mark.

Who Will Love This Experience?

This cruise is perfect for families wanting a kid-friendly holiday activity, couples looking for a romantic festive outing, or friends wanting a lively, joyful cruise. It’s also ideal for travelers who enjoy live music, scenic water views, and holiday decorations. If you’re craving a relaxed but lively way to celebrate the season in Key West, this cruise fits the bill.

Frequently Asked Questions

Is this cruise suitable for children?
Yes, children are welcome. While alcohol is only for 21+ guests, children can enjoy the holiday treats, hot cocoa, and the festive music.

How long is the cruise?
The cruise lasts approximately 1.5 hours, making it a manageable, fun holiday activity without taking up too much of your day.

What should I wear?
Dress comfortably and warmly, especially since it’s December. Layers are recommended to stay cozy during the boat ride.

Are drinks included?
Yes, each ticket includes two complimentary drinks—beer, wine, or champagne—for guests 21 and older. Additional beverages can be purchased onboard.

Can I cancel my reservation?
Yes, you can cancel up to 24 hours in advance for a full refund, providing flexibility during busy holiday times.

Is seating assigned?
Seating may be assigned, so early arrival is advised if you have preferences for where to sit.

What’s the meeting point?
Meet at 202 William Street, directly behind the Schooner Wharf Bar.

Are there any restrictions?
Smoking is not allowed onboard, so plan accordingly. Bring your ID or passport for proof of age if you intend to drink.

Will the cruise be canceled in bad weather?
While not explicitly stated, most boat cruises are subject to weather conditions. It’s always good to check the cancellation policy or contact the provider if weather looks questionable.

Final Thoughts

If you’re in Key West during the holiday season and want to enjoy a festive, lively, and scenic experience, this Christmas music cruise offers a charming way to celebrate. The blend of live entertainment, holiday decorations, drinks, and treats creates a warm, joyful atmosphere that’s both relaxed and lively.

Ideal for those who love a little musical merriment, scenic water views, and holiday cheer, this cruise is a surefire way to create memorable moments with family or friends. Its affordability, comfort, and festive vibe make it one of the more enjoyable ways to embrace the season in Key West.

Whether you’re a first-time visitor or a seasoned traveler, this cruise offers an authentic taste of holiday spirit on the water—something you won’t soon forget.