Southwest Airlines has quietly built one of the bigger Caribbean networks among US carriers, with nonstop service to 10 island destinations from mainland gateways including Orlando, Baltimore, Tampa, Chicago Midway, Houston Hobby, Nashville, Kansas City, Fort Lauderdale, Austin, St. Louis and Indianapolis.
The current map covers Aruba, Grand Cayman, Havana, Montego Bay, Nassau, Punta Cana, Providenciales, San Juan, St. Thomas and St. Maarten. That mix suits very different trips: passport-free escapes to Puerto Rico and the US Virgin Islands for US citizens, all-inclusive weeks in Punta Cana or Montego Bay, diving and beach time in Grand Cayman, or a windward beach break in Aruba.
San Juan is the airline's biggest Caribbean operation, with nonstop flights from about 10 mainland cities and a heavy Orlando schedule. From there it's an easy pivot from an Old San Juan weekend to El Yunque, Vieques or Culebra. Montego Bay is nearly as well connected, with service from seven gateways feeding Jamaica's resort corridor and onward trips to Negril and the north coast. Punta Cana draws from seven cities too, opening up the Dominican Republic's dense concentration of all-inclusives across Bávaro, Cap Cana and Uvero Alto.
The newer additions are notable. St. Thomas routes from Orlando and Baltimore launched in February 2026, and St. Maarten followed in April with daily Orlando flights plus a Saturday Baltimore service — both islands doubling as hopping-off points for St. John, Anguilla, St. Barth and Saba. Providenciales, Nassau and Grand Cayman are served from Orlando and Baltimore, while Havana runs from Tampa only, and US restrictions mean travel there must fit an authorized category rather than plain tourism.
Expansion continues: from 13 March 2027, Southwest adds Saturday routes from Nashville to Aruba, Montego Bay and St. Thomas, plus a new Columbus–Punta Cana flight. No new islands, but four existing ones get fresh mainland gateways.
For travellers, the practical point is that Southwest's Caribbean map is real and growing — and since routes and frequencies shift seasonally, especially on Saturday-oriented vacation flights, it's worth checking schedules for your exact dates before booking. The sweet spot for US travellers without a passport: San Juan and St. Thomas, no passport required.