USVI Vacation Planning: Best Island Holidays

Planning your next trip to the US Virgin Islands? If you always tend to come during the same time of year, perhaps it might be time to branch out and experience St. Thomas and St. John during a celebratory season.

Here are a couple of times of the year where the USVI has something extra special to offer:

Rolex Regatta (Late March)

Love sailing? Visiting during the International Rolex Cup Regatta is exhilarating, whether you’re participating in the sailing or just watching the races. All of the activities are based out of the St. Thomas Yacht Club. You can find more details and the event schedule here.

St. Thomas Carnival (April – May)

St. Thomas hosts the USVI’s largest carnival celebration and it’s a cultural event worth seeing. Typically held in April, it is a whirlwind of colors, music, and revelry. The streets of Charlotte Amalie come alive with parades featuring elaborate floats adorned with local artistry and performers in dazzling costumes. Calypso and steel pan music fill the air, creating an irresistible rhythm that gets everyone dancing. Vendors line the streets, offering local delicacies like johnnycakes and conch fritters, giving visitors a taste of authentic island cuisine. There are endless opportunities for visitors to join in on the fun.

St. John Carnival (June – July 4th)

While events kick off in June, the majority of the St. John Festival celebrations happen the week of Independence Day. St. John’s carnival is a bit more low key in comparison to St. Thomas’ – more intimate and community-oriented in feel. The island’s tight-knit community comes together to celebrate with parades, pageants, and music festivals. Visitors can immerse themselves in the local culture, enjoying traditional dances such as quadrille and the infectious beat of quelbe music.

Christmas & New Year’s (December 24th – January 3rd)

If you have the time & means to visit during the holidays, it’s worth doing at least once. While it is the priciest time of the year to visit the USVI, there’s something uniquely delightful about celebrating Christmas in the sunshine on the beach. The entire week between Christmas and New Year’s feels like a party with tons of special events and activities to partake in. It’s also the time of year when the biggest yachts in the world are cruising through our waters. Pro tip: Because this is the busiest week of the year, we recommend booking your activities and dining reservations well in advance of your trip.

Feeling inspired? Mark your calendars! You can visit the USVI’s Tourism page for specific dates for each year. And once you determine the dates of your next trip, be sure to peruse our website to map out your trip’s activities. We are your All in One Resource for all things FUN in the VI – allowing you to book your boat trips, excursions, ecotours, water sports, and more in one trusted place.