Southwest Airlines is heading to the U.S. Virgin Islands, marking the carrier's first new destination since 2021 and signaling a major shift in the airline's growth strategy. For travelers wondering why Southwest should be your airline of choice, this expansion demonstrates the carrier's commitment to serving popular leisure destinations.

For more TPG news delivered each morning to your inbox, sign up for our daily newsletter.

The Dallas-based carrier announced Monday it will launch nonstop service to St. Thomas in the U.S. Virgin Islands, with flights beginning in early 2026. The move breaks Southwest's three-year route freeze and adds the ninth Caribbean destination to the airline's growing tropical network.

Southwest's first new destination since 2021

For Southwest, gaining access to the U.S. Virgin Islands represents a particularly significant milestone. Beyond adding a stunning new tropical destination, it's the airline's first new market entry in nearly half a decade.

The last new pin on Southwest's route map came in late 2021, when it added Syracuse Hancock International Airport (SYR) in upstate New York during the COVID-19 pandemic, when domestic travel dominated. However, recent years have seen Southwest actually trim its route map, including exiting Syracuse entirely.

That's about to change dramatically.

3 new Caribbean destinations coming soon

Southwest said Monday that St. Thomas is just the beginning. The carrier plans to announce a total of three new destinations for 2026 — St. Thomas plus two more that the airline hasn't yet revealed.

While the remaining destinations will undoubtedly spark speculation among aviation enthusiasts, Southwest also hasn't disclosed which U.S. cities will serve St. Thomas's Cyril E. King International Airport (STT).

The carrier told industry publications it doesn't want to reveal its hand to competitors before tickets go on sale — which is expected to happen soon.

A Southwest Airlines aircraft at Baltimore/Washington International Airport (BWI)

For what it's worth, Southwest's most significant expansion over the past two years has focused on Orlando International Airport (MCO) for Caribbean service, plus continued growth at Baltimore/Washington International (BWI). We'll know soon enough whether it's one of those airports, or a different Southwest hub, that gets this new STT nonstop service.

Southwest's Caribbean strategy takes shape

Located in the Caribbean, St. Thomas (and the U.S Virgin Islands as a whole) makes for an ideal travel destination: all the warm weather and pristine beaches you'd expect from a tropical paradise, but without needing a passport — unless you plan to take a boat trip to the nearby British Virgin Islands.

The territory has seen significant tourism infrastructure investment in recent years, including new luxury resorts and the upcoming Hilton property opening later this year. For travelers planning Caribbean getaways, Hotels.com offers comprehensive accommodation options across the region.

"We are listening closely to what our customers want — from new products and loyalty benefits to new destinations," Southwest CEO Bob Jordan said in a statement Monday.

Several major U.S. airlines currently serve St. Thomas, with American Airlines maintaining the largest presence, followed by Delta Air Lines, JetBlue Airways, and United Airlines. Southwest's entry will bring its signature low fares and flexible policies to the market.

For travelers looking to compare flight options to Caribbean destinations, Skyscanner provides comprehensive search capabilities across multiple carriers and routes.

A strategic Caribbean hub emerges

Southwest's Caribbean expansion has been methodical but impressive. The airline now serves eight Caribbean destinations from its Orlando hub alone, including recent additions like Grand Cayman, Nassau in the Bahamas, Turks and Caicos, and Punta Cana in the Dominican Republic.

St. Thomas will become Southwest's ninth island destination in the Atlantic Basin, joining:

• Aruba
• The Bahamas (Nassau)
• Cayman Islands (Grand Cayman)
• Cuba (Havana)
• Dominican Republic (Punta Cana)
• Jamaica (Montego Bay)
• Puerto Rico (San Juan)
• Turks and Caicos (Providenciales)

This growing Caribbean footprint positions Southwest as a major player in the leisure travel market, competing directly with traditional carriers that have long dominated these popular vacation routes.

Perfect timing for Southwest's transformation

The St. Thomas announcement comes as Southwest undergoes its most significant operational changes in decades. The airline is set to introduce assigned seating and premium cabin options in the third quarter of 2025, followed by a complete fleet reconfiguration featuring extra legroom seats and new fare bundles in early 2026.

The new St. Thomas service will launch right alongside these product enhancements, giving passengers Southwest's traditional perks — like two free checked bags and no change fees — plus the airline's new premium offerings.

For travelers planning Caribbean trips, investing in quality luggage like Samsonite can make the most of Southwest's generous baggage policy, while Priority Pass provides airport lounge access during connections.

"We want to make Southwest Airlines the easy and obvious choice every time, and this is another meaningful step in our ongoing transformation," Jordan added.

What this means for Rapid Rewards members

For Southwest Rapid Rewards members, the addition of St. Thomas creates new redemption opportunities in one of the Caribbean's most desirable destinations. Southwest's award chart typically offers some of the best value redemptions in the industry, especially for domestic and near-international flights.

The airline's points-based system means award flights are tied to cash fares, so the lower Southwest keeps its St. Thomas prices, the fewer points you'll need for an award ticket. With Southwest's history of competitive Caribbean pricing, this could become a sweet spot for points redemptions.

For travelers seeking deals on Caribbean flights beyond Southwest, Going.com offers flight alerts and discounted international fares, while Expedia provides package deals combining flights and hotels. Southwest also offers its own vacation packages through Southwest Vacations, which often include hotel discounts and bonus Rapid Rewards points.

Insider tip: If you're looking to build your Southwest points balance for future Caribbean travel, consider the Southwest Rapid Rewards cards, which offer generous sign-up bonuses and accelerated earning on Southwest purchases.

U.S. Virgin Islands tourism gets major boost

For the U.S. Virgin Islands, landing Southwest represents a significant tourism victory. The territory has been working to expand airlift and attract more visitors, particularly from the U.S. mainland.

"We are excited at the announcement of new airlift into St. Thomas with Southwest Airlines," said Commissioner Joseph Boschulte of the U.S. Virgin Islands Department of Tourism. "As a destination, this expands our accessibility and connectivity to travelers, allowing for seamless and expanded travel opportunities."

For more information about planning your U.S. Virgin Islands vacation, visit VisitUSVI.com.

Governor Albert Bryan Jr. echoed the enthusiasm: "Today marks an exciting milestone for the U.S. Virgin Islands and our growing tourism industry. We are proud to welcome this new partnership with Southwest Airlines and look forward to greeting new travelers to our beautiful island home."

The bigger Caribbean picture

Southwest's St. Thomas addition reflects the airline's strategic focus on leisure-heavy routes that complement its domestic network strength. Unlike legacy carriers that serve business travelers with international long-haul routes, Southwest has carved out a profitable niche in near-international leisure destinations. This approach mirrors the airline's successful partnership with China Airlines, which expanded connectivity options for passengers.

The airline's Caribbean strategy appears to be working, and recent improvements like Southwest's integration with Google Flights have made it easier for travelers to discover and book these routes. Recent data shows Southwest's international routes — primarily to Mexico, Central America, and the Caribbean — have become some of its strongest performers in terms of load factors and revenue.

With three new destinations planned for 2026, Southwest seems committed to expanding this successful formula.

The bottom line: Southwest's St. Thomas announcement breaks a three-year route freeze and signals the airline's renewed focus on growth. For travelers seeking affordable access to one of the Caribbean's most beautiful destinations — with no passport required — Southwest's entry could be a game-changer. Combined with the airline's upcoming product enhancements, 2026 is shaping up to be a transformative year for Southwest's Caribbean network.