In February 1948, Harry S. Truman stepped onto the dock of the Charlotte Amalie under the bright Caribbean sun. The presidential yacht USS williamsburg It was anchored in the harbor behind it. This trip consisted of a break (winter break in Washington), but with a more deliberate twist.
Truman spent his time fishing and sailing off St. Thomas and St. Croix, and appearing in Christiansted to speak at government buildings. The U.S. Virgin Islands have been a U.S. territory for over 30 years. Tourism was modest. Truman saw the potential. His visit placed the island in the national imagination at a moment when air travel began to shrink distances and the postwar American middle class began to look outward.
He understood that the president’s presence, even if only briefly, served as an endorsement. If the President of the United States can vacation here, so can Americans.
In modern terms, this was the first clearly non-state trip to the Caribbean by a sitting president. At least that was after George Washington’s trip to Barbados in 1751, long before he took office.
Truman’s visit did not set off an immediate wave of presidential trips to the South. In fact, the list that follows is surprisingly short. But it establishes an important fact. The Caribbean region is a place not only for diplomacy and strategy, but also for presidential retreats. For your information, this is the place where the president actually becomes president. went on vacation — This is not where they come for state business.
Virgin Islands: Familiar yet Far
There is a practical logic to using the U.S. Virgin Islands as a presidential refuge. They offer the Caribbean without passport lines. American governance along with Danish period architecture. Reef-lined beaches within U.S. territory and an airport capable of accommodating Air Force One.
Bill Clinton attended St. Petersburg in the late 1990s. I found that balance when I spent part of the holiday season in a private villa overlooking Magens Bay in Thomas. The north’s winding roads and elevated views have long attracted travelers seeking privacy without isolation. The president was given both.
Twenty years later, the Virgin Islands have reemerged as a presidential vacation destination.
Starting in December 2022, President Joe Biden and his family have chosen St. Croix for their year-end holidays. They returned in 2023, and again in 2024. Each visit followed the same quiet rhythm, arriving after Christmas and leaving shortly after New Year’s Day.
St. Croix carries a different energy than its sister island. Christiansted and Fredericksted also function as visitor hubs and working cities. The beach is wide and often uncrowded. The dining scene is sharp, with a confident and distinct Crusian edge. You can walk along the promenade in the evening. Sitting on a north coast beach, you can feel like it’s just out of reach.
Biden has achieved an unusual feat in presidential travel records by spending three consecutive winters. He made Caribbean vacations a pattern.
In doing so, he received St. Croix has become the most consistent vacation spot for Caribbean presidents.
Jimmy Carter’s Caribbean Chapter
Jimmy Carter’s relationship with the Virgin Islands unfolded in two acts.
In January 1981, a few days after leaving office, Carter traveled to the U.S. Virgin Islands for a vacation, spending time in St. Thomas and St. John. It was a trip after my public service ended. It was decompression in warm air and distance from the headlines.
Almost 30 years later he returned.
In late 2009, Carter and more than 30 members of his extended family vacationed on St. Croix, staying at the Comanche Hotel in Christiansted. They attended the Crucian Christmas festivities. They passed through the village on foot. They visited Buck Island. It was not a private island. It was multigenerational, public and distinctly local.
That image of a former president watching a holiday parade in a small Caribbean town with his grandchildren next to him feels closer to the spirit of the region than any motorcade.
Jamaica and the wider Caribbean
The Virgin Islands may be central to the Caribbean presidential story, but it is not alone.
In late 1960, before the inauguration, President-elect John F. Kennedy visited Round Hill, Jamaica. This resort, located west of Montego Bay, has already established itself as a retreat for artists and politicians. Kennedy’s stay added a new layer to the story. White villas against a backdrop of green hills, the lights of the north coast sharp into the sea — Jamaica offered a distance without exile.
Ronald Reagan later visited the Caribbean during his presidency, providing at least a brief respite from Washington’s pace by mixing official tours with island visits.
The Bahamas also has a long history of portraying American politicians. Especially after they leave office. Close to Florida and discreet in nature, the island offers privacy without being isolated.
Short list by design
What stands out over the past century is not how often presidents vacationed in the Caribbean, but how rarely they did so.
Maine, Texas ranches, the Cape Cod region, Hawaii, Delaware — domestic vacation destinations dominate presidential records. Security logistics and political optics favor familiar ground.
But when a president heads south, the moment tends to last.
Truman’s 1948 visit still forms part of Virgin Islands legend. Carter’s vacation at the Comanche Hotel is a story told in Christiansted. Biden’s repeated St. Croix holidays have woven the island into the story of recent presidencies.
The Caribbean has always represented something specific in the American imagination. Warmth when the mainland is cold, a horizon instead of a corridor, an ocean instead of a schedule.
The office may feel very far away, at least for a few days.
