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Celebrate Christmas in Key West with a festive 1.5-hour sail on Schooner America 2.0, featuring live band, holiday treats, drinks, and stunning waterfront views.
The Key West Christmas Cruise with Live Band and Drinks offers a cheerful, family-friendly way to enjoy the holiday spirit on the water. Priced at $88.15 per person, this 1 hour and 30 minutes sail takes place aboard the beautifully decorated Schooner America 2.0, bustling with holiday lights and festive decor. The tour departs from 202 William St in Key West at 7:00 pm, making it an ideal evening activity during the holiday season.
What makes this cruise stand out is its lively combination of Christmas music, holiday treats, and waterfront scenery. It’s a perfect option for those looking for a relaxed, cheerful way to soak in the evening air while celebrating Christmas, especially for families or groups seeking a casual yet memorable holiday experience. The tour includes two drinks of beer, wine, or champagne for guests aged 21 and over, with additional drinks available for purchase. The friendly staff and consistent five-star ratings from previous guests confirm this cruise’s appeal.

The Schooner America 2.0 is decked out with holiday lights that instantly bring a festive mood. This family-friendly cruise is designed to boost holiday cheer as it glides through Key West harbor. The boat’s full holiday decor enhances the experience, making it a cheerful backdrop for photos and joyful moments.
During the cruise, the live band plays classic Christmas songs, encouraging guests to sing along and create a lively, communal atmosphere. The crew fosters a warm environment, contributing to the overall sense of celebration. The 1.5-hour duration offers just enough time to enjoy the scenery, music, and treats without feeling rushed.
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As the sailboat gently moves along the waterfront, guests enjoy stunning views of Key West’s harbor and surrounding waters. The cruise provides a relaxed way to see the area from a different perspective, with the harbor lights and water reflections adding to the festive mood.
The boat remains close enough to the Key West waterfront for guests to appreciate the city’s charming skyline and twinkling lights. The cruise’s timing at night ensures that the views are especially enchanting, perfectly aligning with the holiday theme.

The cruise offers holiday treats, adding a sweet touch to the celebration. Guests receive two drinks of their choice—beer, wine, or champagne—which can be enjoyed as the boat sails along. For those desiring more, additional beverages are available for purchase using credit cards.
The inclusion of hot cocoa and festive snacks complements the seasonal atmosphere, making the experience cozy and indulgent. The drinks and treats serve to enhance the overall joyful vibe of the cruise.

The meeting point at 202 William St in Key West is easy to find and close to public transportation options. The activity begins promptly at 7:00 pm and ends back at the same location, making logistics simple for guests.
The tour accommodates most travelers, and service animals are permitted, ensuring accessibility for guests with specific needs. The group size is capped at 75 travelers, maintaining a comfortable and enjoyable environment.
Previous reviews highlight the friendly staff as a key part of the experience. One reviewer notes that staff friendliness made the sailing “a huge delight,” emphasizing good service and a welcoming atmosphere. Parking is also described as convenient, adding to the tour’s practicality.
Guests consistently rate this cruise 5 out of 5 stars, calling it a “can’t miss” holiday activity. The lively music, beautiful views, and festive decor combine to offer a fun and memorable way to celebrate Christmas in Key West.
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At $88.15 per person, the cruise offers good value considering the included live music, holiday treats, and drinks. Booking typically occurs 65 days in advance, indicating a popular choice during the holiday season.
The tour features a free cancellation policy if canceled at least 24 hours before the scheduled start, providing flexibility to adjust plans if needed. This makes it a low-risk option for holiday planning.
This cruise appeals most to families, couples, and groups seeking a cheerful, water-based holiday activity. Its relaxed pace, lively live band, and festive decor make it ideal for holiday celebrations or special outings.
It’s particularly suitable for those who enjoy scenic waterfront views, holiday music, and casual drinks in a cheerful environment. The most important strengths are the friendly staff, beautiful decor, and stunning evening views.
The Key West Christmas Cruise delivers a delightful way to enjoy holiday festivities on the water. Its full holiday decor, live band, and inclusive treats set a lively, warm scene. For $88.15, guests get a well-rounded experience with great scenery, friendly service, and festive cheer.
While the cruise is not focused on a formal or elaborate program, its casual, joyful atmosphere makes it a great pick for those looking to celebrate Christmas in a relaxed setting. Most guests find it well worth the price, especially given the easy logistics and positive reviews.
“The staff was very friendly, which made the sailing a huge delight. Parking is convenient. Loved the music.”
How long does the cruise last?
The cruise lasts approximately 1 hour and 30 minutes.
What is included in the price?
The price includes the 1.5-hour holiday cruise, holiday treats, and two drinks of beer, wine, or champagne for guests 21+. Additional drinks can be purchased onboard.
Is the cruise suitable for children?
Yes, the cruise is family-friendly and suitable for most travelers. Service animals are also allowed.
What is the cancellation policy?
Guests can cancel for free up to 24 hours before the start time for a full refund. Cancellations made less than 24 hours in advance are not refunded.
This Key West Christmas Cruise offers a warm, lively way to celebrate the holidays by the water. With its cheerful decor, friendly staff, and scenic views, it stands out as a festive and relaxing holiday outing in Key West.