Southwest Airlines Expands Caribbean and Latin American Reach with New St. Thomas Route and Growing Network in Aruba, Cuba, Jamaica, Mexico, and Costa Rica

Southwest Airlines has announced its latest expansion into the Caribbean, revealing plans to introduce nonstop service to the island of St. Thomas in the U.S. Virgin Islands. Flights to Cyril E. King International Airport are expected to commence by early 2026, pending final regulatory approval. Ticket availability for this new route is slated to open soon.

The planned launch marks the first of three new destinations the airline intends to unveil this summer as part of its 2026 growth strategy. With this move, Southwest deepens its commitment to connecting more travelers to leisure-oriented locations across the Atlantic Basin.

St. Thomas is set to become the ninth island destination in the Atlantic region to be added to Southwest’s growing network. It will join an impressive lineup that already features Aruba, The Bahamas, Cayman Islands, Cuba, the Dominican Republic, Jamaica, Puerto Rico, and the Turks and Caicos Islands. Beyond the Caribbean, the airline also connects travelers to Belize, two key cities in Costa Rica, and three locations across Mexico—highlighting its continued expansion throughout Latin America and the broader tropical travel market.

The selection of St. Thomas reflects a strategic emphasis on tropical destinations that appeal to both vacationers and those seeking convenient access to U.S. territories. As a U.S. Virgin Island, St. Thomas allows Americans to travel without a passport, making it a particularly attractive addition to Southwest’s portfolio.

In tandem with the launch of new destinations, Southwest is also rolling out a series of major service upgrades designed to improve the overall passenger experience. Beginning in the third quarter of this year, the airline will introduce assigned seating—a significant shift from its long-standing open boarding policy. Alongside this, premium seating options will also be made available.

The carrier is preparing to unveil a reconfigured fleet in the first quarter of 2026, which will include extra legroom seating and updated cabin layouts. These changes are part of a broader initiative aimed at enhancing comfort, flexibility, and value for travelers.

The addition of St. Thomas not only offers greater connectivity to the U.S. Virgin Islands but also aligns with ongoing regional efforts to boost tourism, encourage economic development, and support local hospitality industries. By adding this route, Southwest is expected to facilitate increased visitor arrivals and offer more affordable travel options for leisure travelers and families alike.

This route expansion arrives at a time when demand for Caribbean vacations is surging. With travelers showing growing interest in warm-weather destinations and direct flight options, Southwest’s new service to St. Thomas positions the airline to capture a larger share of this high-demand market.

The launch also signifies a broader shift in Southwest’s operational model. Historically known for its domestic U.S. network, the airline has in recent years expanded its reach into international and island destinations, recognizing the evolving needs of travelers seeking sun-soaked getaways, cultural immersion, and easy-to-reach resorts.

The airline’s evolving offerings—ranging from upgraded seating to new bundled fares—are expected to roll out in conjunction with its 2026 schedule. As part of its modernization and transformation plan, Southwest is aiming to become a more versatile carrier while retaining its core values of affordability and customer service.

St. Thomas marks a pivotal addition to that journey. As the first of several new destinations to be unveiled in the coming months, this move sets the tone for a new era of expansion for the airline. Travelers can look forward to more convenient access to island escapes and enhanced onboard experiences, all while enjoying the reliability and familiarity of a trusted U.S. carrier.

With the U.S. Virgin Islands now in the spotlight, Southwest’s 2026 outlook is shaping up to be a milestone year—combining destination growth, service innovation, and stronger customer engagement in one ambitious roadmap for the future.