Tl;dr – This news dropped a few weeks back but got a little lost in all the hoopla about baggage fees and fare bundles.
A few weeks ago, Southwest resurfaced with more information on its new fare structure, baggage fees, all of which I, candidly, ignored. I’ve mentioned a few times that Southwest Airlines is, and has been, for a long time, ‘dead to me,’ so it probably comes as no surprise that lost in that hoopla was a teaser announcement of the airline’s intention to open up service to St. Thomas. Tickets for these St. Thomas routes are now on sale, so let’s take a closer look.
Southwest to Serve St. Thomas, U.S. Virgin Islands, Beginning in Early 2026
Beginning Feb. 5, 2026, Southwest will fly between Orlando and St. Thomas’s Cyril E. King International Airport (STT), with Baltimore flights taking off two days later on Feb. 7. As mentioned, tickets for these routes are already on sale on Southwest’s website.
I gotta recognize the game when I see it, and this is a solid development for Southwest. At the very least, it’s good to hear some positive news for travelers from the carrier. I’m not even a USVI fan (in my opinion, there aren’t any good hotels there), but this move is a sound strategic one and can unlock some true ‘value travels.’ Take a peek at the maps below courtesy of FlightConnections.
Here’s a graphic of all the direct flights to/from STT:
Several of the US airports featured, which American, Delta, and United currently service, also happen to be airports where Southwest has a solid presence. Starting with Baltimore and Orlando allows Southwest to get some easy Ws under its belt before moving into more competitive markets. Baltimore (BWI) is one of its major hubs, and Orlando (MCO), in addition to being a traditional connecting point for the carrier, counts Spirit Airlines as the only carrier operating to STT. Thus, choosing those airports as starting points is a near-surefire way to fly-and-thrive before gearing up for more competitive markets with the Big Three.
This second graphic is where the value travels come in:
St. Thomas via smaller carriers like Cape Air has solid intercaribbean connectivity to hard-to-get-to destinations like Saint Barth’s, Tortola (EIS) (BVI > USVI all-day), Anguilla’s The Valley (AXA), and St. Croix. A few of these islands only fly to Miami, which isn’t super convenient (nor always enjoyable), so I could see how expansion of this St. Thomas service to other existing Southwest hubs could open up some fun backdoor-build-your-own-connections to some of the more high-end Caribbean destinations. Last year, I visited the Rosewood Little Dix Bay (review forthcoming) and flew into Tortola via Miami. While I made it to the resort, my bag did not, as American Airlines lost it in Miami (of course they did), and my luggage got to spend a few more days ‘partying in the city where the heat is on,’ Big Wilie Style of course.
Notably, by the end of the summer, Southwest will announce two additional new destinations it will fly to in 2026. The next reveal will be sometime in August.
