Presidents in Paradise: A History of U.S. Presidents Visiting the Caribbean

By Publisher Ray Carmen

From wartime strategy meetings to tropical summits and disaster response, the Caribbean has long played host to U.S. Presidents seeking diplomacy, development—or just a break from the Washington grind. Though often overlooked in the broader arc of foreign policy, presidential visits to the region tell a compelling story of evolving American engagement with its southern neighbors.

Let’s take a journey through time to see which U.S. Presidents left their footprints on Caribbean sands—and what brought them there. 

Franklin D. Roosevelt: New Deals and Naval Eyes

Few presidents spent as much time in the Caribbean as FDR. During the 1930s and ‘40s, Roosevelt made several trips to Puerto Rico, the U.S. Virgin Islands, and the Bahamas. Initially visiting to inspect New Deal projects, his wartime visits to the Bahamas reflected the region’s strategic importance. He also sailed through the Caribbean on naval vessels, reinforcing its role in both policy and leisure. 

Harry S. Truman: Testing Self-Governance

In 1948, Truman visited Puerto Rico to observe progress on local governance and economic reform. He supported the transition toward greater autonomy, planting early seeds of Puerto Rico’s evolving political identity. 

John F. Kennedy: Economic Vision in the Tropics

In 1961, Kennedy visited Puerto Rico, promoting Operation Bootstrap—a program to industrialize the island. His visit symbolized support for economic development and strategic alignment during the Cold War. 

Lyndon B. Johnson: Civil Rights, Island Style

President Johnson continued Caribbean engagement with trips to Puerto Rico and the Virgin Islands. His focus remained on poverty alleviation and equal rights, echoing his broader domestic agenda. 

Richard Nixon: Summit Diplomacy in the Bahamas

In 1973, Nixon met with British Prime Minister Edward Heath in the Bahamas for a high-level strategic summit. Though his Caribbean travels became more personal post-resignation, his official visit marked an important Cold War-era gesture. 

Gerald Ford: G7 Meets the Tropics

Ford hosted a G7 Summit in Dorado Beach, Puerto Rico in 1976—the only such summit ever held in the Caribbean. It was a bold move that brought global leaders to the tropical territory and underscored Puerto Rico’s geopolitical relevance.

George H. W. Bush: Jamaica and Beyond

Bush visited Jamaica twice—once as Vice President (1982), and again as President (1989)—reinforcing ties with key allies. He also maintained ties with Puerto Rico through regular check-ins and economic initiatives. 

Bill Clinton: Restoring Democracy in Haiti

In 1995, Clinton made a historic visit to Haiti following a U.S.-led intervention to restore its democratically elected leadership. His presence signaled a renewed U.S. commitment to regional stability. 

George W. Bush: Caribbean in Crisis

George W. Bush’s presidency saw the Caribbean hit by multiple crises. He visited Haiti and Jamaica between 2004 and 2007 to coordinate disaster relief and engage with CARICOM leaders, emphasizing hemispheric cooperation. 

Barack Obama: Energizing the Region

Obama’s Caribbean diplomacy was as forward-looking as it was symbolic. In 2009, he attended the Summit of the Americas in Trinidad and Tobago, met young leaders in Jamaica in 2015, and visited Puerto Rico in 2011—the first president to do so in 50 years. His energy-focused agenda resonated with island nations facing climate and development challenges. 

Donald Trump: Post-Hurricane Politics

Trump traveled to Puerto Rico in 2017 in the aftermath of Hurricane Maria. The trip, meant to highlight federal response, instead drew controversy for its tone. Nonetheless, it marked another moment of high-stakes presidential presence in the region. 

Joe Biden: Quiet Steps in the Sand

While President Biden hasn’t made an official Caribbean visit yet, he vacationed in the U.S. Virgin Islands in 2022. His administration has participated in several regional forums, indicating the Caribbean remains on the U.S. radar.

Why It Matters

Presidential visits to the Caribbean aren’t just symbolic; they’re strategic. The region serves as a crossroads of diplomacy, trade, migration, and security. Each visit, whether for summitry or support, underscores a longstanding—if uneven—relationship.

In the face of climate change, economic challenges, and shifting global alliances, the Caribbean continues to call for meaningful engagement. Whether from the White House or the beaches of Barbados, U.S. presidents will likely keep answering.