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Southwest Launches St. Thomas Service After Years of Negotiations and Hurricane-Related Setbacks

Southwest Airlines’ inaugural flight to St. Thomas marked the culmination of more than 4 years of negotiations, hurricane-related setbacks, and renewed engagement led by the V.I. Port Authority and territorial partners to expand airlift into the territory

  • Ernice Gilbert
  • February 06, 2026
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Passengers aboard Southwest Airlines’ inaugural flight to St. Thomas disembark at Cyril E. King Airport, where they were greeted with a celebratory welcome marking the airline’s first arrival to the U.S. Virgin Islands.

Passengers aboard Southwest Airlines’ inaugural flight to St. Thomas disembark at Cyril E. King Airport, where they were greeted with a celebratory welcome marking the airline’s first arrival to the U.S. Virgin Islands. Photo Credit: GOV'T HOUSE.

ST. THOMAS — The arrival of Southwest Airlines’ inaugural flight at Cyril E. King Airport on Thursday capped more than four years of negotiations, setbacks, and renewed engagement, a process that V.I. Port Authority Executive Director Carlton Dowe said required persistence, coordination, and long-term commitment across multiple agencies and administrations.

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Speaking at the airport ceremony, Dowe stated that the airline’s decision to launch service to St. Thomas was not automatic, noting that aircraft can be deployed anywhere and that securing a new carrier requires deliberate effort. He recounted early discussions with Southwest years ago that stalled after hurricanes disrupted travel and development across the territory, temporarily halting momentum on airlift expansion.

According to Dowe, those conversations were later restarted through renewed outreach involvingVIPA, the Department of Tourism, and territorial leadership. He described the effort as a rekindling of relationships rather than a new initiative, crediting sustained dialogue and cooperation for ultimately bringing Southwest back to the table.

Dowe also highlighted the Port Authority’s role in facilitating new airline service, explaining that incentives such as reduced landing and operational fees are available to carriers opening new markets, but only through approval and alignment with the authority’s governing board. He credited the board, chaired by Willard John, for supporting the strategy that helped secure Southwest’s arrival.

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Governor Albert Bryan Jr. framed the launch as both an economic and social milestone, emphasizing affordability and access for Virgin Islands residents who depend on stateside travel for healthcare, family obligations, and essential services. He highlighted Southwest’s low-cost model as particularly significant for island residents who regularly travel to and from the mainland.

Bryan also positioned the new service within a broader territorial strategy, describing St. Thomas as a gateway not only to the Virgin Islands but to the wider Caribbean. He said the administration is working to expand multi-island and regional connectivity, linking airlift growth to ferry expansion, port development, and efforts to position the territory as a hub for Caribbean travel.

Tourism Commissioner Jennifer Matarangas-King echoed that timeline, telling attendees the partnership had been more than four years in the making and that such agreements are built through relationships rather than single negotiations. She acknowledged the work of former Tourism Commissioner Joseph Boschulte and Assistant Commissioner Alani Henneman, who played key roles in earlier airlift discussions.

Representing Southwest Airlines, Adam Decaire said the carrier views the Virgin Islands as a long-term partner and welcomed the territory into what he described as the Southwest “family.” He said the airline’s expansion reflects its focus on building durable relationships with communities it serves.

Throughout the ceremony, speakers stressed that the launch was the result of behind-the-scenes work often unseen by the public. Officials rejected the notion that airline arrivals happen naturally, crediting instead the planning, negotiation, and coordination required to bring a major carrier to the territory.

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While Thursday’s landing marked a milestone, Dowe and other leaders framed it as the start of an ongoing partnership. Multiple officials expressed optimism that continued collaboration would lead to expanded service and additional benefits for the territory.

 

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