Southwest Airlines is officially heading to the U.S. Virgin Islands for the first time ever. Beginning in early 2026, Southwest will launch service to Cyril E. King International Airport (STT) in St. Thomas, making the USVI its newest Caribbean destination.
This is a major expansion move for the airline and a welcome addition for travelers looking for more flexible, affordable ways to reach the Caribbean—especially using Rapid Rewards points. For U.S. citizens, the appeal is even stronger: no passport required.
What We Know So Far
The announcement came directly from Southwest on July 14, 2025, noting that service will begin in early 2026, pending government approvals. While specific routes and schedules haven’t been released yet, flights to St. Thomas will be available for booking soon.
This marks the airline’s first new destination since 2021 and its ninth island destination in the Atlantic Basin. It joins a growing list that includes Aruba, the Bahamas, Turks & Caicos, Puerto Rico, and Jamaica.
Why This Matters for Travelers
At first glance, Southwest adding service to St. Thomas might seem like a win for travelers looking to reach the U.S. Virgin Islands using Rapid Rewards points. But when you dig a little deeper, the value proposition isn’t what it used to be.
While Southwest was once a favorite among budget travelers for its simplicity and perks, recent changes—including the end of free checked bags for most fares, upcoming assigned and premium seating, and a shift to fully dynamic pricing—have made their award redemptions far less appealing. They’re also behind other major carriers when it comes to premium benefits and saver fare flexibility.
Personally, I’ve been prioritizing American Airlines for my Caribbean redemptions. Between the elite benefits, access to Admirals Clubs, and great saver award availability, the travel experience with AA far outweighs the current Southwest offering. You can see how I booked a last-minute trip to the US Virgin Islands using points from American Airlines and United for just 49,000 points total roundtrip for two people, in this post:
How I Booked an $8,700 St. Thomas Vacation Using Points and Miles
In that same trip, we stayed at The Westin Beach Resort & Spa at Frenchman’s Reef for five nights using 331,000 points, taking advantage of Marriott’s fifth-night-free benefit. Even though Marriott’s dynamic pricing often makes redemptions feel steep, we still saved nearly $6,750 on the hotel portion alone. If you’re sitting on Free Night Certificates from the Marriott Bonvoy Business Card or looking to use Amex and Chase Offers for additional savings, this can still be a high-value redemption.
However, if you’re trying to fly to the USVI using points, American Airlines and United often provide far better value and flexibility. Southwest’s upcoming service to St. Thomas is worth keeping an eye on—but as someone who values premium perks, predictable pricing, and elevated travel experiences, I’m not convinced it’s a game-changer just yet.
U.S. Virgin Islands: No Passport Needed
One of the most overlooked perks of traveling to the U.S. Virgin Islands is that you don’t need a passport if you’re a U.S. citizen. This makes it ideal for travelers who either don’t have a passport or want to travel internationally without dealing with border control.
The three main islands are St. Thomas, St. John, and St. Croix, and each one offers something different—from luxury resorts and duty-free shopping to national parks and pristine beaches.
Final Thoughts
Southwest’s entrance into the U.S. Virgin Islands is a win for travelers who prioritize value, flexibility, and ease of access. It also highlights a growing demand for more accessible Caribbean routes as leisure travel continues to rebound.
As more route details become available, I’ll keep you updated on the best ways to book, redeem points, and plan your trip to St. Thomas. This could be a great opportunity to hotel hop or pair with a cruise itinerary. Make sure you’re subscribed to the blog so you don’t miss those updates.
