Southwest Expands to St. Thomas: First New Destination in Five Years

Southwest Airlines is set to expand its route network for the first time in five years, unveiling plans for a new flight to the U.S. Virgin Islands, with service expected to launch in early 2026.

While the airline has kept details under wraps regarding the cities from which these flights to Cyril E. King International Airport (STT) on the island of St. Thomas will operate, it has sparked a wave of anticipation among residents and travelers alike.

Growing in the Caribbean

St Thomas will be Southwest’s ninth Caribbean destination, alongside existing links to Aruba (AUA), the Bahamas (NAS), Cayman Islands (CGM), Cuba (HAV), Dominican Republic (PUJ), Jamaica (MBJ), Puerto Rico (SJU), and Turks and Caicos (PLS). Most of these flights depart from Southwest’s hub in Baltimore (BWI) or from Florida, both likely sources of the Virgin Islands flight.

Aerial view of St. Thomas / Photo: Steve Heap, Adobe Photo Stock

Virgin Islands locals welcomed the new flight. St. Thomas is already connected to the mainland United States by American, Delta, United, and Spirit.

Commissioner Joseph Boschulte of the U.S. Virgin Islands Department of Tourism: “As a destination, [the Southwest flight] expands our accessibility and connectivity to travelers, allowing for seamless and expanded travel opportunities to experience the natural beauty, vibrant culture, and warm hospitality that define the U.S. Virgin Islands.”

Recalibrating Strategy After the Pandemic

St. Thomas is one of three new destinations Southwest will reveal this summer, as it transitions away from its post-pandemic strategy of strengthening service to existing destinations and ventures into new locales.

In May, Southwest CEO Bob Jordan told the Bernstein Strategic Decisions Conference in New York that the airline is “going to be thoughtful” as it expands its network.

Photo: Courtesy of David Syphers / Unsplash

That month, Southwest asked the U.S. Department of Transportation for blanket authority to operate scheduled flights to other U.S. Open Skies partners, suggesting the airline was targeting more international destinations, perhaps further afield than the Caribbean.

“We’ve been serving international markets for over a decade—closer in, Caribbean, Mexico, that kind of thing,” Jordan said at the conference. “But the open skies application is really intended just to make these processes easier. So, as we decide that we want to move into other geographies, it makes that decision [simpler].”

Hints of Bigger Plans to Come

The U.S. Virgin Islands is a U.S. territory and thus not an international destination that requires an Open Skies permission, but could Southwest’s next two mystery destinations be more exotic?

Last month, Jordan told CNBC that his carrier could someday launch flights to Europe. Southwest has also recently minted its first international partnership with Icelandair and China Airlines.

Photo: Courtesy of Southwest Airlines / Stephen M. Keller

Southwest’s hangars currently exclusively house Boeing 737s, so the airline would need to acquire long-range aircraft for any trans-Atlantic or trans-Pacific flights. So we wouldn’t expect Southwest jets to turn up on any new continents just yet.

But it will be interesting to see where else Southwest heads next year.

“We are listening closely to what our customers want—from new products and loyalty benefits to new destinations,” Jordan said in a statement. “We want to make Southwest Airlines the easy and obvious choice every time, and this is another meaningful step in our ongoing transformation.”

Transforming—For Better or Worse?

Despite Jordan’s spin, Southwest’s reinvention hasn’t been entirely guided by passengers. The airline, under pressure from activist investors Elliott Investment Management and desperate to turn a profit again, has also scrapped its famous “two free bags” policy, slashed points earning on its cheapest fares, and introduced complicated fare bundles.

Photo: Courtesy of Southwest Airlines

Jordan suggested recently that these changes, largely introduced this spring, haven’t alienated the carrier’s budget-conscious consumer base. Southwest hopes that other tweaks, including assigned and premium seating, set to arrive later this year, will attract new customers, including those looking for a splash of luxury.