Key West Christmas Cruise with Live Band and Drinks

If you’re dreaming of celebrating Christmas in a unique, relaxed way, a holiday sail in Key West might just be what you need. This Key West Christmas Cruise promises a festive atmosphere aboard a beautifully decorated schooner, with lively music and holiday treats. While I haven’t personally experienced it, the reviews and details paint a picture of an enjoyable evening that combines stunning scenery with holiday cheer.

What really catches our eye about this cruise is how family-friendly it is and how it offers a cozy, communal celebration on the water. Plus, the live band playing Christmas music adds a lively, authentic touch that’s perfect for getting into the spirit. Another aspect that stands out is the focus on waterfront views—there’s something special about seeing Key West’s lights and landscape from the water, especially with a holiday twist.

Of course, no experience is perfect for everyone. One consideration is the price point, which is about $88 per person—good value, but not the cheapest option, especially when you factor in optional drinks and gratuities. Also, since the tour lasts only about an hour and a half, you’ll want to set your expectations for a quick, festive getaway rather than an extended cruise.

In the end, this cruise seems like a solid choice for those wanting a short, cheerful holiday experience in Key West. If you enjoy sailing, lively music, and scenic views, this could be a highlight of your Christmas trip down south.

Key Points

• Festive Decor & Atmosphere: The schooner is decked out with holiday lights, setting a cheerful scene.
• Live Music & Singing: A live band plays Christmas tunes, making the experience lively and engaging.
• Waterfront Views: You’ll enjoy stunning vistas of Key West’s harbor and waterfront, especially at night.
• Inclusive Drinks & Treats: Two drinks are included, with additional options available for purchase.
• Family-Friendly & Near Public Transport: Suitable for most travelers, with service animals allowed.
• Short & Sweet: The ride lasts about 90 minutes, perfect for a quick holiday outing.

The Experience in Detail

The Setting & Decor

From the moment you step onto the 105-foot Schooner America 2.0, you’re greeted with holiday cheer. The boat is decorated with lights, giving it a warm, festive glow that immediately puts you in a holiday mood. The fact that it’s a sailing schooner adds a touch of classic nautical charm, especially at night when the harbor lights reflect off the water.

The Itinerary & Viewpoints

The cruise begins at 202 William St, right in the heart of Key West. Once underway, you’ll glide along the waterfront, taking in sights of the harbor, boats, and, depending on the night, perhaps even some nearby islands. Since the cruise is focused on holiday sightseeing, you can expect to see Key West’s water and shoreline illuminated with holiday lights, making for a beautiful backdrop.

While there’s no mention of multiple stops, the main attraction is undoubtedly the water views and the overall festive ambiance. The cruise smoothly circles around, giving everyone a chance to soak in the sights without feeling rushed.

The Atmosphere & Entertainment

The highlight is undoubtedly the live band playing Christmas favorites. Reviews mention how the staff was friendly, contributing to a welcoming environment, making the sailing a “huge delight.” People sing along, which adds to the sense of community and holiday cheer. This is definitely a family-friendly experience, but it’s equally suited for couples or groups of friends looking for a fun, relaxed evening.

Drinks & Treats

Included in your ticket are two drinks—beer, wine, or champagne—so you can toast to the holiday spirit. Additional drinks are available for purchase, which can be handy if you’re thirsty or want to indulge a bit more. Holiday treats are also served, adding to the cozy vibe, perfect for warming up on a cool winter’s night over water.

Duration & Logistics

The cruise lasts roughly 1 hour and 30 minutes, making it a manageable activity without feeling overly long. It starts at 7 PM, which is ideal for enjoying the harbor lights after sunset.

Meeting at 202 William St is easy to find, and the activity is near public transportation, making access straightforward. Since service animals are allowed, it’s accessible for travelers with specific needs.

What We Think About the Value

At $88.15 per person, this cruise is priced similarly to other experiences in Key West, but it offers a lot for that cost. The included drinks, holiday treats, and lively entertainment mean you’re paying for more than just a boat ride—you’re investing in a cozy, festive memory.

While the ticket price doesn’t include gratuity, the overall experience’s intimacy, scenic views, and holiday cheer seem worth it—especially if you’re seeking a special way to celebrate Christmas. The reviews reinforce this, with one calling it a “can’t miss” experience, thanks to the friendly staff and enjoyable music.

Who Is This Tour Best For?

This cruise is perfect if you want a short, festive activity that combines scenic harbor views with holiday cheer. It works well for couples, groups of friends, or even families, thanks to its family-friendly nature and relaxed vibe. It’s especially suited for those who enjoy sailing, live music, and a cheerful atmosphere, but it may not be ideal if you’re looking for a longer or more elaborate cruise experience.

FAQs

Is this tour suitable for children?
The experience is generally family-friendly, and it’s designed to be a cheerful holiday celebration, so children can enjoy it too. Just keep in mind the duration and the fact that drinks are available for those 21+.

Can I bring my service animal?
Yes, service animals are allowed on the cruise, making it accessible for travelers with special needs.

What time does the cruise start?
The cruise begins at 7:00 PM, ideal for catching the sunset and evening harbor lights.

Are additional drinks available on board?
Yes, extra beverages can be purchased via credit card during the cruise.

How long is the cruise?
The cruise lasts approximately 1 hour and 30 minutes, making it a manageable evening activity.

What is the meeting point?
Meet at 202 William St, Key West, FL 33040. It’s near public transportation, making it easy to access.

Final Thoughts

For anyone looking to add a dash of holiday magic to their Key West visit, this Christmas sail on Schooner America 2.0 offers a cozy, scenic, and lively way to celebrate. The combination of stunning harbor views, live holiday music, and festive decor makes it stand out as a memorable part of your holiday season. While it’s a relatively short adventure at just under 90 minutes, the joyful atmosphere and beautiful night scenery can leave a lasting impression.

It’s best suited for those who want a relaxed, cheerful holiday activity that combines scenic beauty with good company and music. If you’re after a lively, water-based celebration that captures the spirit of Christmas in Key West, this cruise deserves a spot on your holiday itinerary.

Remember, booking in advance is recommended since it’s popular—on average, it’s reserved about 65 days ahead. So, if this sounds appealing, plan ahead to secure your spot for a night filled with holiday cheer on the water.