Southwest Is Getting Into the Vacation Business With Getaways by Southwest — Including in the Caribbean
Southwest Airlines is moving deeper into the vacation business with the launch of its new in-house packaged vacations product, Getaways by Southwest.
The program, now available to customers, brings together air, hotel, car, and ground transportation options into a single bundled booking — extending Southwest’s hallmark flexibility to full vacation packages.
“Getaways by Southwest expands what Customers love about Southwest — flexibility, an award-winning Rapid Rewards loyalty program, and great perks — to the vacation experience,” said Phil Gouel, Vice President of Product Development at Southwest Airlines. “This end-to-end vacation package, coupled with our legendary Customer Service, is perfect for Customers seeking a convenient, valuable, and curated vacation experience.”
Packages will include many of Southwest’s core destinations, with a focus on leisure markets such as Las Vegas, Orlando, Hawaii — and, notably, Caribbean hotspots like Punta Cana in the Dominican Republic and Montego Bay, Jamaica. For those destinations, the move deepens Southwest’s footprint in the all-inclusive and resort-heavy vacation space, creating new opportunities for travelers looking to pair low-cost air with bundled hotel and ground transport.
Customers booking a Getaway will receive key benefits including two free checked bags (weight and size limits apply), the ability to earn five Rapid Rewards points per dollar spent, and flexible cancellation terms. Packages can be changed without fees, and if plans change entirely, travelers receive travel credits valid for up to 18 months.
For Montego Bay and Punta Cana, the launch positions Southwest more competitively against other U.S. carriers with long-established vacation divisions, adding a new option for the Caribbean’s two most-visited resort destinations.
The expansion comes as other U.S. airlines are deepening and reshaping their own vacation divisions. JetBlue recently rebranded its Paisly offering to streamline vacation add-ons, while legacy competitors like American and Delta continue to expand their holiday packaging with more Caribbean and Mexico inventory.
Caitlin Sullivan began her career with Caribbean Journal as Arts and Culture editor before shifting to travel full time. She writes frequently on the Caribbean cruise industry, flight networks and broader travel news. Her most frequent Caribbean destination? Nassau.
