Southwest Just Launched Two Daily Flights to a Caribbean Island With Endless Beaches, Famous Bars, and a Passport-Free Vacation

Southwest Airlines has officially landed in the U.S. Virgin Islands. This week, Southwest launched daily round-trip service to St. Thomas from both Orlando and from Baltimore, opening up one of the Caribbean’s most beloved beach and bar destinations to even more travelers. It’s perfect for anyone who prefers water that’s warm enough to swim in year-round, rum poured without hesitation, and a rhythm of travel that doesn’t require passports or currency conversion.

St. Thomas is a quintessential Caribbean island with a distinctly American ease: U.S. dollars, domestic airports, no customs, and familiar connections. The new flights — daily from Orlando and from Baltimore — both launched this week.

They give travelers flexibility and frequency that change the calculus on quick escapes or longer stays. It’s now just as simple to do a long weekend in the sun as it is to plan a full week of snorkel days and seaside dinners.

What makes this especially noteworthy isn’t just the fact of new service; it’s where Southwest has chosen to show up. St. Thomas isn’t a single-beach postcard. It’s a layered destination with snorkel coves, historic harbors, beaches that feel like hidden gems, and bars that are vacation memories waiting to happen.

More Flights to a Buzzing Destination

St. Thomas has been a mainstay on Caribbean itineraries for decades — and it’s been hotter than ever in the post-pandemic era. But this new service is an extra boost. It is on American soil, which means domestic flight rules apply, and new travelers who might otherwise hesitate to navigate an international trip suddenly have a downright easy path to the tropics.

Southwest’s decision to fly both Orlando and Baltimore daily is also a market sign. Orlando feeds a huge leisure audience already accustomed to sun and sand, and Baltimore reflects a strong East Coast demand horizon for Caribbean travel during winter and shoulder seasons. What both flights together do is create real schedule depth, meaning travelers can book without having to hinge their entire trip around a single flight window.

But the deeper story is what you find after you land. St. Thomas doesn’t just offer beaches — though it has those in abundance — it also offers a diversity of experience. There are coves perfect for a calm swim or snorkel (or kayak through the mangroves), historic harbors with a patina of Caribbean commerce, local neighborhoods with real afternoon energy, and plenty of ways to shape a trip around what you want — whether that’s water, food, bars, or a bit of all of the above.

Beaches That Don’t Feel Like a Checklist

One of the great joys of St. Thomas is how distinctive each beach feels. Magens Bay is the island’s headline act — a wide, palm-framed curve of sand with calm, clear water that makes it easy to spend hours just floating, swimming, or watching the water turn from turquoise to deep blue as the day moves on. It’s the kind of place where you feel the Caribbean stereotype, and then some.

But within minutes in different directions, you find other kinds of beaches. Lindquist Beach has a more local feel and fewer crowds, and the snorkeling is often better right off the shore.

Then there’s Brewers Bay, which has a different personality entirely: a more open, easygoing stretch with fewer distractions, the kind of beach where you bring a towel, grab something cold, and settle in for the afternoon. It’s also a strong choice for travelers who want a quieter swim and a more authentic feel without driving far. Over on the East End, Vessup Bay gives you a softer, calmer shoreline with water that tends to stay gentle, and it’s a smart pick when you want a beach day that feels unhurried.

And then there’s Hull Bay, one of the island’s most character-filled spots. It’s also one of the best places on the island to end the day, when the light drops and the water starts to look metallic in the distance.

That variety is part of St. Thomas’s charm: each beach delivers a slightly different version of island life.

Bars That Tell the Story of the Island

St. Thomas has a famous bar culture, and the best places aren’t trying to feel like something they’re not. They simply are places where rum flows, music plays, and views feel like part of the order.

Duffy’s Love Shack is the classic example — bright neon, loud music, generous drink pours, and an atmosphere that simply feels like vacation without apology. It’s right in Red Hook (the gateway to St John), and it’s one of those places where arriving early doesn’t matter because you’ll still be there hours later with a rum cocktail in hand and a grin you didn’t have before.

Then there are beachfront bars where the drinking is done with sand underfoot and water within sight. At the relaunched Iggies Beach Bar, you can order something rum-forward and watch the ocean shift color as the sun moves across the sky. There’s an ease to these places that makes them feel like part of the daily rhythm rather than an event.

And for those who prefer a view with their drink, the hilltop spots above Charlotte Amalie offer breezes and harbor panoramas. It’s one thing to sip a cold drink at sea level, but it’s another to watch the harbor lights come alive from above, especially as the day moves toward dinner. (We love the Mountain Top and its sea-view painkillers).

St. Thomas isn’t only about beach bars or neon nightlife. It’s about a bar culture that reflects the island’s multifaceted personality — lively without pretense, social without stress, and always with water in view.

The Part of St. Thomas Travelers Don’t Expect

St. Thomas carries a reputation as a beach island, and that’s fair. But the island’s real strength is its ability to pivot into different kinds of experiences without losing its Caribbean heartbeat.

Charlotte Amalie, the capital, is a harbor town that feels like it was built with a map of Caribbean history in hand. Colonial architecture, storefronts with decades — if not centuries — of stories behind them, and waterfront cafes make it easy to spend an afternoon walking and learning the island’s past even as you plan your next swim.

Frenchtown, on the other side of the harbor, has its own rhythm — more neighborhood than tourist zone, with eateries and bars that feel earned rather than staged. A meal here is as much about the people you see as the food on the plate.

And the island’s geography means adventure is never far. St. Thomas is the launchpad to neighboring Water Island or St. John, where beaches inside Virgin Islands National Park are such singular experiences that travelers build entire half-day excursions around them. By boat or ferry, these hops are easy to add to a St. Thomas trip, giving you the feeling of island variety without the logistics of switching airports or packing bags.

St. Thomas, in other words, is both a destination and a starting point.

Where to Stay Right Now

If you want something with real local flavor — the kind of place where classic Caribbean chill is the objective — Bolongo Bay Beach Resort is a smart choice. It sits right on the water in Bolongo Bay, a cove that shelters calm, clear water perfect for waking up and slipping straight into fins and mask. The vibe here is relaxed and social, with water taxi service to popular bars in the afternoon and boats cruising in for sunset. For travelers who want beach time without fuss, and a community of fellow beach lovers within easy reach of town energy, Bolongo Bay feels just right. And did we mention the snorkel rum hunt?

For travelers looking for refined comfort with big-picture service and amenities, The Ritz-Carlton, St. Thomas sets a different tone. Overlooking Great Bay, the resort brings spacious rooms, elevated dining, and a full suite of wellness and watersports options to a more classic luxury format. The scale here is larger, the service is polished, and there are plenty of places to sit with a cocktail and watch the harbor traffic drift by. It’s a strong fit for couples, families, or anyone who wants a resort foundation that still keeps the island close at hand.

Both properties capture facets of St. Thomas life — one more beach-centric and local, the other more hotel-oriented and elevated — giving travelers real choice in how they want to experience the island.

What This Means for Travel Right Now

With daily service from Orlando and Baltimore already underway, it’s easier than ever to book a trip based on mood rather than months of planning. That’s part of what the Caribbean has always been about: a sense of escape that doesn’t feel like a production.

St. Thomas delivers exactly that — beaches with personality, bars that are part of the day’s rhythm, and layers of island culture to explore between swims. With more flights and more flexibility, it’s a place worth rediscovering or discovering for the first time.

Prices on the new Southwest Flights

You can find fares from Orlando to St Thomas for about $466 roundtrip right now, based on what we saw on Google Flights. From Baltimore, they’re a bit higher, at $616 roundtrip.