Southwest Just Opened a New Door to the Caribbean

Southwest Airlines touched down in St. Maarten for the first time on April 7, and the implications for Caribbean travel are bigger than one new route.

Daily nonstop flights now run from Orlando to Princess Juliana International Airport (SXM). Weekend service from Baltimore started on April 11. And because of how Southwest's network works, those two gateways connect to more than 45 other U.S. airports. That means travelers from secondary cities like Nashville, Pittsburgh, and Raleigh now have a one-stop path to one of the Caribbean's most interesting islands.

Why this route matters

St. Maarten is Southwest's first new international destination since adding Cozumel earlier this decade. That's not a small deal. Southwest doesn't add international routes casually. The airline needs to see sustained demand potential before committing planes and crew to a new market.

For travelers, the real significance is pricing pressure. Southwest's entry into Caribbean routes has historically forced competitors to lower fares. When Southwest started flying to San Juan years ago, average fares from the mainland dropped measurably. The same competitive dynamic should play out on the St. Maarten route, benefiting everyone who flies there, not just Southwest passengers.

The other advantage is Southwest's baggage policy. Two free checked bags per passenger, no change fees. On a Caribbean trip where you're packing snorkel gear, beach supplies, and enough sunscreen to last a week, that saves a family of four $200 or more in baggage fees compared to most other carriers.

What makes St. Maarten worth visiting

The island is split between two countries. The southern half, Sint Maarten, is a Dutch territory. The northern half, Saint-Martin, is French. You can cross the border freely, no passport check needed, and experience two distinct cultures, cuisines, and vibes on an island you can drive across in 20 minutes.

The Dutch side has the famous Maho Beach, where planes landing at Princess Juliana Airport pass just 30 to 40 feet overhead. It sounds gimmicky. It's genuinely thrilling. The beach bar there, Sunset Bar and Grill, posts the daily flight schedule so you know exactly when to look up.

The French side is quieter, with better restaurants and a more European feel. Grand Case, a tiny village on the north coast, has more quality restaurants per square foot than most small towns anywhere in the world. Locals call it the "gourmet capital of the Caribbean," and the claim holds up. A three-course dinner at a beachfront French restaurant runs $40 to $60 per person.

Orient Bay on the French side has the best beach on the island. A mile of white sand with beach clubs, water sports, and clear water that looks photoshopped but isn't.

Where to stay

Hotel pricing on St. Maarten varies dramatically between sides. The Dutch side has more resort-style properties with all-inclusive options. The French side leans toward boutique hotels and villas.

Mid-range hotels on the Dutch side run $150 to $250 per night. The French side averages $180 to $300. Vacation rentals through local agencies (not just Airbnb) often offer better value, especially for groups. A three-bedroom villa with a pool on the French side can run $250 to $350 per night, which splits to under $120 per couple.

Booking early matters here. With Southwest bringing a wave of new visitors, the properties closest to popular beaches will fill faster than they used to. Travelers who book rooms now through a cashback platform like Best (best.so) lock in current rates plus 10% back.

The practical details

Southwest's Orlando to St. Maarten flight runs daily. The Baltimore route operates Saturdays and Sundays during peak travel weeks. Flight time is roughly 3.5 hours from Orlando.

U.S. citizens need a valid passport to enter St. Maarten. No visa required for stays under 90 days on either side of the island. The local currency is the Netherlands Antillean guilder on the Dutch side and the euro on the French side, but U.S. dollars are accepted almost everywhere.

April through June is shoulder season with comfortable temperatures in the mid-80s and lower hotel rates. Hurricane season runs August through November. The sweet spot for value and weather is April, May, early June, and then again in December.

Frequently asked questions

Does Southwest fly to St. Maarten daily?

Southwest operates daily nonstop flights from Orlando (MCO) to St. Maarten (SXM) as of April 7, 2026. Weekend service from Baltimore (BWI) started April 11. Connecting flights from 45-plus U.S. cities are available through these hubs.

Do I need a passport for St. Maarten?

Yes. U.S. citizens need a valid passport to enter St. Maarten. No visa is required for stays under 90 days on either the Dutch or French side of the island.

Which side of St. Maarten is better for tourists?

The Dutch side (Sint Maarten) has more nightlife, casinos, and the famous Maho Beach plane-spotting experience. The French side (Saint-Martin) has better restaurants, quieter beaches, and a more European atmosphere. Most visitors spend time on both sides since crossing the border takes minutes.

Images: Hero by Cody Board. Caribbean beach by Sean Oulashin. All via Unsplash, used under license.