St Thomas offers a fantastic backdrop for Christmas celebrations, especially if you love being on the water. The island’s warm trade winds, stunning coastlines, and lively maritime scene make holiday boat tours more than just a cruise—they’re a festive event. We especially like the Christmas Cove and Pizza Pi Happy Hour Sail Tour for its relaxed vibe and unique floating pizza restaurant, and the Christmas Eve Sunset Sail With Santa for adding that special holiday touch to the Caribbean sunset. Whether you’re looking for a lively sunset with drinks and swimming or a cozy holiday chat with Santa, St Thomas has options that fit different tastes.
These experiences stand out for their blend of scenic beauty, fun onboard atmosphere, and holiday spirit. Plus, the small group sizes mean you get a more personal, memorable outing—perfect for celebrating with family or friends. If you’re planning your holiday visit, consider booking early—these popular options sell out fast during the season.
Quick Overview
Our list of top Christmas Tours & Experiences in St Thomas covers two standout options: a sunset sail with happy hour, swimming, and floating pizza [], and a festive Christmas Eve cruise with Santa onboard []. Both offer a mix of scenic sailing, holiday fun, and unique onboard treats. Read on to see which fits your holiday style.
1. Christmas Cove and Pizza Pi Happy Hour Sail Tour
This 3-hour sunset sail is one of the most relaxed and engaging Christmas experiences in St Thomas. The tour departs from Red Hook around 3:30 PM, heading to Christmas Cove—a favorite for its crystal-clear waters. The highlight is the chance to swim in warm, calm waters and enjoy the fun of ordering pizza from the Virgin Islands’ only floating pizza restaurant, Pizza Pi. Their menu offers some of the best pizza in the Virgin Islands, making this a tasty stop.
What makes this tour special is the combination of happy hour drinks, including Caribbean Rum Punch, beer, soft drinks, and bottled water, along with a fully stocked bar on board. The sail back at sunset, with the sky glowing above, makes for a perfect Caribbean evening. The small group sizes—typically fewer than 10—ensure personalized service. Guests often rave about Captain Eric and First Mate Casey, citing their attentiveness and friendly demeanor.
This tour appeals most to visitors who enjoy swimming, casual dining, and a laid-back vibe. The overall value is excellent, considering the inclusions—food, drinks, and the scenic sail. It’s a good choice for couples, friends, or anyone wanting a relaxed, scenic sunset with fun onboard activities.
Bottom Line: A charming, easygoing sunset sail with excellent food and drink options, perfect for those who want to blend relaxation with a bit of adventure.
2. Christmas Eve Sunset Sail With Santa
For around $119, this 2-hour Christmas Eve sailing experience offers something more festive, with Santa himself onboard. Unlike standard sunset cruises, this event is designed to incorporate holiday cheer into the Caribbean setting. The boat departs in the late afternoon, offering spectacular views as the sun dips below the horizon.
What sets this tour apart is the holiday interaction with Santa, who walks around the deck chatting with guests, sharing holiday stories, and spreading cheer. There’s no rushed photo op—this is about hanging out with Santa in a relaxed atmosphere. The boat’s route takes in some of the most beautiful coastlines in St Thomas, with plenty of opportunities for photos and enjoying the warm sea breeze.
Though it has no reviews yet, the concept of blending a sunset cruise with a Christmas celebration makes it a memorable option for families or anyone wanting to extend holiday magic. It’s a more intimate experience suited for those seeking a festive, relaxed, and family-friendly celebration.
Bottom Line: An excellent choice for families or those wanting to combine holiday traditions with Caribbean scenery, bringing a bit of Santa magic to the sea.
$119
How to Choose
When deciding between these two Christmas experiences in St Thomas, consider your holiday style and what kind of memories you want to make. If you love a relaxed sunset sail with drinks, swimming, and pizza, the Christmas Cove and Pizza Pi Happy Hour Sail Tour is perfect. It’s great for casual groups and offers a low-key, fun way to celebrate.
On the other hand, if meeting Santa and enjoying a Christmas-themed cruise appeals to your sense of holiday magic, the Christmas Eve Sunset Sail With Santa offers a more festive, family-friendly option. It’s ideal for those who want a cozy, holiday-specific experience.
In either case, booking early is advised, especially during the peak Christmas season, as these tours tend to fill up fast. Think about your preferred pace—whether you want to unwind with drinks and swimming or enjoy holiday cheer with Santa onboard—and pick the experience that best suits your style.
Final Thoughts
St Thomas provides lively and memorable ways to celebrate Christmas on the water. The Christmas Cove and Pizza Pi Happy Hour Sail Tour offers a laid-back, scenic evening with great food and drinks, while the Christmas Eve Sunset Sail With Santa adds the magic of holiday cheer with Santa himself. Both tours deliver beautiful views, fun onboard atmospheres, and a chance to create special holiday memories.
For travelers seeking a relaxed, scenic cruise, the pizza and sunset sail is ideal. Families or those wanting holiday magic with a personal touch will enjoy sailing with Santa on Christmas Eve. Whatever your choice, early booking is key—these experiences are popular during the holiday season. Prepare to enjoy a festive, fun, and memorable Christmas in St Thomas.