Key West: Live Christmas Holiday Music Cruise with Hot Cocoa

A Festive Touch in the Keys: The Key West Christmas Music Cruise

When you think of Key West, visions of lively sunsets, colorful boats, and tropical charm probably come to mind. But during the holiday season, the island offers a special treat — a Christmas-themed cruise aboard the Schooner America 2.0. It’s a cheerful way to celebrate the season with loved ones, combining the magic of the holidays with the laid-back island vibe.

What makes this experience stand out? First, the live Christmas music — a band that invites everyone to sing along is truly infectious. Second, the festive decorations and holiday lights turn the boat into a glowing winter wonderland, quite a contrast to the usual sun-soaked scenery. But, a potential consideration is that this cruise runs only in the evening, so it’s best suited to those who enjoy a lively nighttime outing.

This cruise suits anyone looking for a fun, family-friendly holiday activity or a unique way to celebrate with friends. If you’re seeking a relaxed, joyful experience with a dash of holiday spirit on the water, this could be a perfect addition to your Key West itinerary.

Key Points

• Festive atmosphere with holiday lights and decorations.
• Live Christmas music that encourages sing-alongs.
• Two complimentary drinks (beer, wine, or champagne) for guests 21+.
• Holiday treats and cookies included in the ticket price.
• Duration of 1.5 hours offers a manageable, relaxed experience.
• Meeting point at 202 William Street, conveniently located behind the Schooner Wharf Bar.

You can check availability for your dates here:

An Authentic Holiday Experience on the Water

This 1.5-hour cruise on the Schooner America 2.0 promises a cheerful escape from the typical holiday rush — but with an added twist: your view of Key West is from the water, draped in holiday lights. As we understand, the ship is decked out with twinkling lights, creating a cozy, festive setting that makes even the most jaded holiday soul smile.

From the moment you step aboard, the holiday spirit is in the air. The boat’s relaxed atmosphere invites everyone to kick back and enjoy. The presence of a live band playing Christmas favorites is a highlight; their music is lively enough to get everyone singing along and adds a genuine warmth to the evening. We loved the way the band’s cheerful tunes turned strangers into a singing crowd, making the experience feel personal and unpretentious.

A notable feature is the inclusive drinks—two free beverages per person aged 21 and up. Guests can choose from beer, wine, or champagne, which helps to loosen up the crowd and add a celebratory touch. The holiday treats and cookies are a thoughtful touch, providing a sweet pairing to the drinks and music.

While the cruise doesn’t include a full meal, the holiday treats go a long way in satisfying your sweet tooth and adding to the festive feel. If you’re a light eater or just want to enjoy a drink or two, this setup is practical and straightforward, especially with additional beverages available for purchase on board.

What to Expect from the Experience

The meeting point at 202 William Street, right behind the Schooner Wharf Bar, is a convenient starting point. Once aboard, you’ll find the boat decorated with festive lights, setting the mood right away. The crew is friendly and eager to share the holiday cheer, and seating is likely to be assigned, so arrive early if you want a good spot.

The cruise itself is a leisurely ride around the harbor, offering views of Key West’s waterfront illuminated by holiday lights. The atmosphere is casual — perfect for families, couples, or groups of friends looking to celebrate together. The live band plays a mix of Christmas classics and fun tunes, encouraging everyone to sing along and participate. This isn’t a formal concert but a lively, communal event designed to spread holiday cheer.

The included two drinks are a nice touch, especially since they are from a bar that offers beer, wine, or champagne. This encourages a laid-back, celebratory mood without breaking the bank. If you want more drinks, they are available for purchase, which is typical but worth noting if you’re planning on a longer evening.

As the cruise winds down, you’ll have enjoyed a different kind of holiday—one that combines the spirit of Christmas with the relaxed charm of Key West. The experience is ideal for those who appreciate simple pleasures like good music, scenic views, and a little holiday magic.

The Value of the Experience

At $88 per person, this cruise offers good value for a unique holiday activity. It’s not just about the scenery but about creating memories with music, lights, and cheer. When you factor in the complimentary drinks and holiday treats, it’s an accessible way to indulge in a festive spirit without the high prices of other holiday events.

The 1.5-hour duration makes it a manageable outing, especially if you’re on a tight schedule or have other plans for the evening. Plus, the flexible booking options—including free cancellation up to 24 hours in advance—add peace of mind, ensuring you can plan without stress.

For those traveling with children or seeking a casual family activity, this cruise offers a wholesome, fun environment. Conversely, couples looking for a romantic, cheerful evening will also find it charming, especially with the harbor views and twinkling lights.

Practical Tips for Participants

• Arrive early at the meeting point at 202 William Street to secure a good seat.
• Bring your ID or passport, as the two free drinks are only for guests 21+.
• Dress comfortably and warmly, as it’s an evening cruise and it can get breezy on the water.
• No smoking is allowed onboard, so plan accordingly.
• Remember, seating might be assigned, so early arrival can help you get your preferred spot.
• Consider purchasing additional beverages if you want more than the included two drinks.
• The cruise runs mainly in the evening, so plan your day accordingly if you want to combine it with other daytime activities.

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Who Will Enjoy This Cruise?

This holiday cruise is best suited for travelers who want a lighthearted, festive experience that combines the charm of Key West with cheerful holiday traditions. Families with children who enjoy holiday music will find it delightful, while groups of friends or couples can enjoy the camaraderie and scenic views.

It’s particularly appealing if you’re looking for an easy, relaxed way to celebrate Christmas without the formality or expense of a big dinner. The inclusive drinks and holiday treats make it good value, but it’s not a full meal — so plan your other holiday meals around it if needed.

Travelers who value authentic, local experiences will appreciate the effort to make the cruise feel festive and fun, rather than overly commercialized. Plus, the cozy setting on a historic schooner adds a touch of maritime charm to your holiday memories.

Frequently Asked Questions

Is there a dress code? You don’t need formal attire, but dressing warmly and comfortably is recommended since it’s an evening cruise.

Can I bring children? While the tour is family-friendly, the drinks are only for guests 21 and older. Children can enjoy the music, treats, and holiday decorations.

What if I want more drinks? Additional beverages are available for purchase onboard, giving you the option to extend the festive cheer.

How long is the cruise? The cruise lasts approximately 1.5 hours, making it a convenient and not overly lengthy holiday outing.

Where is the meeting point? It’s located at 202 William Street, directly behind the Schooner Wharf Bar — easy to find and accessible.

Is there free cancellation? Yes, you can cancel up to 24 hours in advance for a full refund, providing flexibility for your travel plans.

What’s included in the ticket price? You get a festive holiday cruise on the Schooner America 2.0, one hot cocoa or beverage, and holiday treats.

Are additional beverages available? Yes, for purchase onboard, if you want more than the two complimentary drinks.

Is seating assigned? Yes, seating may be assigned, so arriving early can help you choose your preferred spot.

In short, this Key West Christmas cruise offers a lively, colorful way to celebrate the holidays on the water. With heartfelt music, festive lights, and a relaxed vibe, it’s an experience that captures the spirit of the season and the charm of the island. Whether you’re a local or visiting, it’s a memorable way to add some extra joy to your holiday trip.

You can check availability for your dates here: