Southwest Airlines Is Adding New Nonstop Flights To A Caribbean Island Where Beaches, Boating, and Shopping All Come Together

By: - December 18th, 2025
southwest airlines caribbean island
Southwest Airlines is adding two new routes to an island with beaches like this.

St. Thomas is the island where beaches sit minutes apart, the harbor stays active from early morning to late evening, and a short ferry ride can turn one vacation into two or three. Magens Bay remains one of the Caribbean’s most photographed beaches. Red Hook continues to anchor the island’s social life with marinas, bars and sunset cruises. Charlotte Amalie still blends duty-free shopping with historic streets that climb sharply into the hills. It is one of the Caribbean’s most complete islands — and now it is getting easier to reach.

New Nonstop Flights To St. Thomas

Southwest Airlines has confirmed new nonstop service to Cyril E. King International Airport, adding daily flights from Orlando and Baltimore beginning in early 2026. The expansion strengthens St. Thomas’ airlift at a time when travelers are prioritizing direct routes and simplified Caribbean access.

Daily round-trip service from Orlando launches Feb. 5, 2026, followed by daily service from Baltimore starting Feb. 7, 2026. Tickets are now available for purchase, marking Southwest’s move from intent to execution after previously signaling plans to serve the U.S. Virgin Islands.

Why These Routes Matter

Orlando functions as one of the country’s most important leisure gateways, drawing travelers from across the Southeast while serving as a major connection point for domestic and international trips. Baltimore reinforces access from the Mid-Atlantic and Delmarva region, a long-reliable source market for the territory.

Together, the two routes add frequency and consistency, making St. Thomas even more accessible for short escapes, repeat visits and island-hopping itineraries that include nearby St. John and the British Virgin Islands.

Things To Do On St. Thomas

St. Thomas delivers variety without complication. Travelers split their days between calm beaches like Magens Bay and Coki Beach, snorkeling reefs just offshore, or chartering boats from Red Hook for half-day sails and full-day island hops. The island’s position makes it one of the Caribbean’s easiest jumping-off points for St. John’s national park beaches or day trips across the channel.

On land, Charlotte Amalie offers walkable shopping, historic forts and dining that stretches from casual waterfront spots to chef-driven rooms. Sunset viewpoints, hillside bars and catamaran cruises round out an island experience that feels full even on shorter stays.

Easy Arrival And Short Transfer Times

One of St. Thomas’ quiet advantages is how quickly travelers can move from plane to beach. Cyril E. King International Airport sits close to the island’s main hotel corridors, meaning transfers are short and straightforward. Combined with direct flights and ferry connections, the arrival experience feels efficient — a factor that continues to drive repeat visitation and short-stay travel. Most importantly, St Thomas is one of the Caribbean islands Americans can visit without a passport; that also means that when you land, there’s no long immigration line, just head for the baggage claim and then to your transportation (with a stop for a Cruzan sample in between, of course).

Two Islands In One Trip

One of St. Thomas’ enduring advantages is how easily it pairs with St. John, effectively turning a single flight into a two-island vacation. Regular ferries run between Red Hook and Cruz Bay, making it simple to move between the islands without changing accommodations or flights.

St. John delivers a different pace and profile. Much of the island is protected as national parkland, anchoring its reputation for unspoiled beaches, clear-water snorkeling and hiking trails that lead to historic ruins and quiet coves. Trunk BayCinnamon Bay and Maho Bay are among the Caribbean’s most recognizable beaches, while Cruz Bay concentrates dining, shopping and nightlife into a compact, walkable hub. For travelers, the pairing works naturally — St. Thomas for energy, access and variety, St. John for scenery, space and immersion in the landscape.

Where To Stay

Bolongo Bay Beach Resort remains one of St. Thomas’ most distinctive places to stay, pairing a relaxed beachfront setting with an all-inclusive experience that feels informal and social rather than scripted. Located just south of Charlotte Amalie, it offers direct beach access while staying close to the island’s main dining and ferry corridors. And then there’s the legendary Iggie’s. 

The Ritz-Carlton, St. Thomas adds a full-service luxury option on the island’s eastern end, set along Great Bay near Red Hook. The resort pairs a traditional beachfront layout with extensive dining, pools and water access, while its marina and charter program make it easy to get out on the water or move between nearby islands. Its location places guests close to ferry service for St. John while remaining removed from the busier parts of Charlotte Amalie.

In St John, The Saint offers a small, design-forward boutique stay near Cruz Bay, popular for its social atmosphere, poolside scene and proximity to the island’s dining and ferry hub.

With new nonstop access from two key U.S. markets and an island experience built around beaches, boating and connectivity, St. Thomas continues to reinforce its position as one of the Caribbean’s most accessible and dynamic destinations.

About the author

Karen Udler is the Deputy Travel Editor of Caribbean Journal. A graduate of Duke University, has been traveling across the Americas for three decades. First an expert on Latin American travel, Karen has been traveling with CJ for more than a decade. She likes to focus on wellness, luxury travel and food.
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