Caribbean Southwest schedules first service outside continental U.S. By Jerry Limone / November 01, 2012 Share 1 -- Southwest Airlines on April 14 will take over AirTran’s San Juan service to two Florida cities. It is Southwest’s first venture beyond the continental U.S. Southwest will operate three daily flights from Orlando and one daily flight from Tampa. The carrier’s AirTran subsidiary will continue to offer service between San Juan and Baltimore, Fort Lauderdale and Atlanta. Southwest said it "soon will determine the best time" to convert the remaining AirTran flights as part of the AirTran integration into Southwest. Southwest cleared its final labor-related hurdle toward operating Caribbean service in September, when flight attendants approved a contract change allowing overwater flying.