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Unforgettable Holiday Travel: 7 U.S.V.I. Celebrations You Won’t Want to Miss

Updated: Dec 11, 2023

'Tis the season to explore new horizons and create lasting memories. It’s the perfect time to plan a visit to the U.S. Virgin Islands, which is filled with unique holiday traditions you won’t find anywhere else - not to mention warm, sunny weather all winter long!


If you’re ready to trade your snow pants for a swimsuit, let us know. We’re here to take the stress out of holiday travel and help you find the perfect St. Thomas home base for your adventures!


A holiday travel scene in the U.S. Virgin Islands

Miracle on Main Street

Dec. 15, 2023


Check out Main Street in Charlotte Amalie, St. Thomas, as it is transformed into a Christmas wonderland - minus the snow! For nearly 30 years, Miracle on Main Street has been drawing visitors with the promise of food, live music, crafts, caroling, local artisans and kids activities. Don’t miss the chance to visit Santa and let him know what you’re hoping to find on Christmas morning.


Holiday Travel Tip: Need transportation to Main Street? St. Thomas does not have Lyft or Uber, but our concierge service is here to help Island Luxury guests schedule a taxi or reserve a rental car. Contact us.


Celebrate Hanukkah with The Hebrew Congregation of St. Thomas

Starting Dec. 7, 2023


Founded in 1796, the St. Thomas Synagogue is the second-oldest continuously operating synagogue in the Western Hemisphere. The historic building is home to a memorial museum and a Torah scroll saved from Nazi destruction during World War II. It’s also the oldest synagogue in America and one of only five in the world with a sand floor representing the exodus of the Israelites from Egypt. Hanukkah celebrations start Dec. 7 with the lighting of the first candle.


Holiday Travel Tip: Visitors are required to RSVP for services. Make your reservation and find more information about visiting hours here.


St. Thomas Lighted Boat Parade

Dec. 15, 2023


Don’t miss this procession of illuminated boats as they parade across Charlotte Amalie’s harbor. This isn’t just any parade - the competition is fierce and the winner for best in show is announced each year after the parade at Crown Bay Marina.


Holiday Travel Tip: Feeling inspired to get out on the water? Contact us for help booking a sunset sail or chartering a boat for the day.


Christmas Tree Lighting at Havensight Mall

Dec. 7, 2023


Just because you’re on vacation doesn’t mean you have to forgo the traditional Christmas evergreen! Head to Havensight Mall to see the lighting of a giant tree with more than 30,000 Christmas bulbs. The party wouldn’t be complete without live music, dancing and an appearance by Santa himself.


Holiday Travel Tip: Want to grab a bite after the event? Check out our favorite restaurants on the Southside of St. Thomas.


Challenge of the Carols

Dec. 25, 2023


The annual Challenge of the Carols is one of the most beloved traditions on St. Thomas - in fact, it’s been held every Christmas morning for the last 47 years! Each year, crowds gather at Emancipation Garden in downtown Charlotte Amalie to hear choirs, performing groups and soloists from all over the island sing their favorite Christmas tunes. After the performance, pop into a local restaurant for a traditional St. Thomas Christmas meal of guavaberry rum, ham and sweetbread!


Holiday Travel Tip: Book your Island Luxury villa or condo as early as possible, as this is one of the most popular times of year to visit the Virgin Islands. Contact us if you need help with a last-minute reservation.


St. Croix Crucian Christmas Festival

Dec. 26, 2023-Jan. 6, 2024


Want a holiday celebration so big it lasts nearly two weeks? Check out the Crucian Christmas Festival on our neighboring island of St. Croix. The party starts the day after Christmas and continues until Jan. 6 with dancing, moko jumbie stilt performers, an early morning J’ouvert celebration, a children’s parade, New Year’s Eve fireworks and more.


Holiday Travel Tip: St. Croix is just 45 miles away from St. Thomas and can easily be reached from any of our St. Thomas vacation homes. Island Luxury guests can contact us for help planning a trip via ferry, seaplane or chartered boat.


Three Kings Day

Jan. 6, 2024


If you visit the islands over the holidays, you’ll notice that the festive vibe continues long after Christmas and the New Year have passed. Three Kings Day, celebrated on Jan. 6, marks the day the three wise men arrived in Bethlehem to deliver their gifts to baby Jesus. It’s celebrated by giving small gifts, eating traditional holiday food and indulging in King’s Cake, a crown-shaped pastry with a tiny plastic baby hidden inside. If you’re offered a slice, choose wisely. Tradition holds that whoever gets the plastic figurine is responsible for hosting the Feb. 2 Candlemas (Festival of Lights) party!


Holiday Travel Tip: Many restaurants and shops are closed on Three Kings Day. You can stock up on groceries and essentials ahead of time by contacting our concierge service to arrange for provisioning.


Start Your Holiday Travel Planning Now


We can’t wait for you to visit the Virgin Islands during this magical time of year! Call or email today for information about holiday reservations and excursion planning.

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