Southwest Airlines is inviting American travelers to escape to turquoise waters and sunlit hillsides with a major new expansion into the Caribbean. Beginning in early 2026, the carrier will operate new nonstop flights to St. Thomas in the U.S. Virgin Islands, marking a significant milestone both for the airline’s growth strategy and for tourism across the territory. For beach seekers, cruise fans, and island hoppers, the announcement signals easier, more affordable access to one of the Caribbean’s most scenic and culturally rich destinations.
A New Chapter in Southwest’s Caribbean Story
For the first time since 2021, Southwest is adding new destinations to its network, and St. Thomas sits at the heart of this renewed international and near-international push. The airline formally announced its intent to serve Cyril E. King International Airport on St. Thomas in July 2025, identifying the island as the first of three new destinations scheduled to debut in 2026. The move expands Southwest’s footprint across the Atlantic Basin, where it already serves islands such as Aruba, Jamaica, and the Dominican Republic.
St. Thomas will become Southwest’s ninth island destination in the region and a key link in a growing portfolio of tropical gateways. Industry observers point to the airline’s strategy of focusing on leisure-oriented, high-demand routes where its mix of competitive fares and frequent service can reshape market expectations. In the case of St. Thomas, the timing aligns with a broader resurgence in Caribbean tourism and a traveler base increasingly willing to prioritize experience-driven trips over material purchases.
The expansion is also part of a wider transformation within Southwest. Alongside the new routes, the airline is introducing assigned seating and premium seat options starting in early 2026, evolving its traditionally open-seating model into a more flexible, product-rich experience. The St. Thomas flights will be among the first to operate in this new era, positioning the island at the intersection of Southwest’s network growth and product overhaul.
Nonstop Access: Orlando and Baltimore Become New Gateways
The heart of the announcement for travelers is the launch of nonstop service from two major U.S. mainland gateways: Orlando International Airport and Baltimore/Washington International Thurgood Marshall Airport. According to the U.S. Virgin Islands Department of Tourism, daily round-trip service between Orlando (MCO) and St. Thomas (STT) is set to begin on February 5, 2026. Just two days later, on February 7, Southwest will introduce nonstop service from Baltimore (BWI), further strengthening the connection between the Mid-Atlantic region and the Caribbean.
Flight schedules, as currently published by local tourism authorities, point to a convenient daytime operation. Orlando departures to St. Thomas are planned late in the morning, arriving midafternoon in the islands, with a return in the late afternoon that brings travelers back to Florida by early evening. The Baltimore service is designed to deliver Mid-Atlantic passengers into St. Thomas around midday, allowing for same-day resort check-ins, ferry connections to neighboring islands, or a relaxed afternoon on the beach.
While all schedules remain subject to change, the structure of these new routes signals a deliberate effort to make weekend escapes and weeklong island vacations easy to plan. For travelers in the greater Washington, Baltimore, and Orlando regions, the need to connect through Miami, San Juan, or other Caribbean hubs will diminish, saving hours of transit time and removing a common barrier to choosing the U.S. Virgin Islands over more accessible Florida beaches.
What This Means for St. Thomas and the U.S. Virgin Islands
For St. Thomas and the broader U.S. Virgin Islands, Southwest’s entry represents much more than an additional airline on the arrivals board. Local officials see it as a significant expansion of airlift capacity that can drive visitor numbers, diversify source markets, and support year-round tourism stability. The islands have long relied on a mix of major U.S. carriers and regional operators to support both leisure and visiting-friends-and-relatives traffic. The arrival of a large low-fare operator based in the mainland United States is likely to put downward pressure on average ticket prices and stimulate new demand from travelers who may have previously considered the Caribbean out of reach.
St. Thomas, home to the capital city of Charlotte Amalie, is already one of the busiest cruise ports in the Caribbean and a primary air gateway for visitors headed onward to St. John and St. Croix. Increased competition and added seat capacity can help smooth seasonal peaks, allowing hotels, restaurants, tour operators, and ferry companies to better balance their operations throughout the year. For local businesses that rely on off-ship spending, the growth in air arrivals offers an important counterweight to the sometimes-volatile cruise industry.
Officials also emphasize the unique advantage of the U.S. Virgin Islands for American travelers: as a U.S. territory, the islands offer a Caribbean escape without the need for a passport for U.S. citizens traveling from the mainland or Puerto Rico. That selling point, combined with the familiarity of a major domestic carrier, could significantly expand the islands’ appeal among first-time Caribbean travelers, families with young children, and older visitors who prefer the comfort of staying under the U.S. flag.
Southwest’s Growing Island Network and Competitive Landscape
The launch of St. Thomas service slots neatly into Southwest’s broader Caribbean and Latin American growth story. Over the past decade, the airline has steadily built a network that links U.S. cities to popular tropical destinations including Aruba, Montego Bay in Jamaica, Nassau in the Bahamas, and several points in Mexico and Central America. Adding St. Thomas, along with forthcoming service to St. Maarten in 2026, helps round out a portfolio that increasingly resembles that of legacy carriers while retaining Southwest’s point-to-point focus.
From a competitive standpoint, the move brings a new dynamic to routes long dominated by major network airlines such as American, Delta, JetBlue, and United, all of which already operate flights into the U.S. Virgin Islands. Low-cost carrier Spirit and leisure-focused operator Sun Country have also established a presence, particularly from East Coast and Midwestern markets. With Southwest’s entry, travelers can expect a fresh round of fare competition, especially around peak holiday periods and school breaks when Caribbean prices typically spike.
The timing also coincides with other capacity boosts into the U.S. Virgin Islands. JetBlue has announced expanded service to St. Thomas, and Sun Country has ramped up seasonal flights from Minneapolis, widening the geographic spread of nonstop access. Collectively, these moves underscore the confidence airlines have in sustained demand for Caribbean getaways, even as economic uncertainties and shifting travel patterns continue to shape the broader industry.
Transforming the Customer Experience: Assigned Seats and Fare Bundles
Southwest’s St. Thomas routes will be among the first to debut under the airline’s updated onboard experience. Beginning January 27, 2026, all tickets on Southwest flights will feature assigned seating, a major departure from the open-seating model that has defined the carrier for decades. Passengers traveling on or after that date will be able to select seats at the time of booking, including access to new premium seating options that offer extra legroom and more favorable cabin locations.
In parallel, the airline is rolling out new fare bundles that package seating preferences and ancillary services into clearer, tiered offerings. For leisure travelers planning a long-awaited Caribbean escape, this shift promises a more predictable and customizable experience. Families can secure seats together without the uncertainty of boarding groups, while couples and solo travelers can decide whether to invest in premium seating or prioritize value.
The new structure could be particularly appealing on longer-haul flights from cities such as Baltimore, where travelers often place extra importance on comfort and predictability. It also brings Southwest’s product closer to that of competitors that already offer a spectrum of seat and fare choices, potentially attracting a new segment of customers who previously overlooked the airline due to its open-seating policy.
Implications for Orlando and Baltimore Travelers
For residents of Central Florida, the addition of nonstop service from Orlando to St. Thomas opens a convenient gateway to the Caribbean that bypasses the need for connections through Miami or other hubs. Orlando has quietly evolved beyond its identity as a theme park capital, becoming a significant origin point for international and leisure travel. Southwest’s decision to anchor its St. Thomas launch with daily Orlando flights recognizes the region’s growing role as a sun-seeker’s origin city in its own right.
The benefits for Baltimore and the broader Mid-Atlantic region are equally compelling. The new nonstop route from BWI gives travelers in Washington, Baltimore, and the surrounding states a direct link to the Caribbean without the need to transit through congested airports farther south. Combined with existing domestic connectivity in Southwest’s network, the St. Thomas flights will be accessible from smaller cities across the Midwest and Northeast via one-stop itineraries, making the island feel more reachable to a wide swath of the United States.
For budget-conscious travelers, Southwest’s entry could also reshape pricing norms. As the airline deploys its well-known policies such as two free checked bags on eligible fares and no change fees, total trip costs to the U.S. Virgin Islands may become more competitive versus other Caribbean destinations. In an era of heightened price sensitivity and rising ancillary charges across the industry, such inclusions can be a deciding factor when families choose where and how far to travel.
A New Era for Caribbean Tourism
The introduction of Southwest’s St. Thomas service captures a broader trend in post-pandemic travel: a strong, sustained appetite for sun, sea, and outdoor experiences. Caribbean destinations have been among the biggest beneficiaries of this shift, drawing repeat visitors and new explorers alike who value open-air activities, natural scenery, and the sense of escape that island life provides. By tying St. Thomas more tightly into the U.S. domestic aviation network, the new flights are likely to reinforce these patterns and encourage more spontaneous, short-notice travel.
For tourism planners in the U.S. Virgin Islands, the challenge and opportunity lie in managing growth sustainably. Increased tourism can generate vital revenue and jobs, but it also places added pressure on beaches, reefs, infrastructure, and local communities. Expectations are rising for destinations to balance visitor volume with environmental stewardship and cultural preservation. St. Thomas, with its historic architecture, busy harbor, and delicate marine ecosystems, will face renewed scrutiny as arriving passengers increase.
Nonetheless, the consensus among tourism officials and industry experts is that the arrival of Southwest marks a positive inflection point. With careful planning, the added airlift can underpin investments in infrastructure, diversify local businesses, and spread economic benefits more evenly across the community. For travelers, it means new possibilities: a long weekend snorkeling among sea turtles, a family holiday split between St. Thomas and neighboring St. John, or a romantic escape timed to coincide with one of the islands’ many festivals.
Planning Your Own Escape to Paradise
As tickets go on sale and departure dates approach, prospective visitors will find it easier than ever to build a Caribbean itinerary centered on the U.S. Virgin Islands. A typical trip might begin with a morning departure from Orlando or Baltimore, followed by a midafternoon touchdown in St. Thomas and a short transfer to a beachside resort or hillside villa. From there, travelers can explore Charlotte Amalie’s historic streets, take a ferry to St. John’s national park beaches, or hop a short flight to St. Croix for a multi-island experience.
The combination of Southwest’s expanded network, assigned seating, and fare bundles offers travelers more control over how they experience the journey. For some, that might mean booking premium seats and traveling light with a single carry-on. For others, it will be about maximizing value by taking advantage of included checked bags and flexible change policies. In every case, the underlying benefit is the same: more choice over how to reach one of the Caribbean’s most compelling island groups.
With nonstop service from key U.S. gateways and growing connectivity from across the mainland, the U.S. Virgin Islands are poised to welcome a new wave of visitors in 2026. For Southwest, the launch represents both a return to growth and a deeper commitment to serving travelers who dream of warm seas and white-sand shores. For travelers themselves, it is an open invitation to escape to paradise, where the journey is simpler, the options are broader, and the horizon over St. Thomas feels closer than ever before.