southwest airlines

Southwest Airlines Is Doubling Flights Between San Diego and Los Cabos

Caribbean Cruise

Cruise Booker: A 3-Night Celebrity Reflection Sailing to CocoCay and Bimini From $443

A quick Caribbean escape doesn’t always mean a full week at sea. One of the easiest cruise getaways right now is a 3-night sailing on Celebrity Cruises’ Celebrity Reflection, departing Fort Lauderdale from May 15 through May 18, with fares starting at $443 per person for an inside stateroom. Travelers looking for a more elevated onboard experience can […]

Flights

Southwest Airlines Is Launching Its First International Redeye Flight — From Las Vegas to Costa Rica

Southwest Airlines is entering new territory this fall. On Oct. 1, the carrier will launch its first-ever international redeye flight, a daily nonstop between Las Vegas’ Harry Reid International Airport and San José, Costa Rica. The new route will be the only nonstop service between Las Vegas and Costa Rica’s capital, and it marks a scheduling shift for an […]

Flights

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 […]

Flights

Southwest Airlines Is Launching Assigned Seating on a Flight From Puerto Rico

southwest airlines puerto rico indianapolis

Southwest Airlines is set to operate its first-ever assigned-seating flight this week, and the launch will include a departure from Puerto Rico. On Tuesday, January 27, a Southwest flight from San Juan, Puerto Rico, to Orlando, Florida will be one of the airline’s first two flights to operate with assigned seating. The flight, WN3575, will […]

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

You feel it the moment you land: the glide over Maho Beach, the bright rush of turquoise beyond the runway, the sense that this island has always been a crossroads. Now St. Maarten is getting another one. Or two, to be exact. Southwest Airlines is launching new nonstop service to St. Maarten beginning in spring […]

Southwest Airlines Is Launching a New Nonstop Summer Route Between Indianapolis and Puerto Rico

Southwest Airlines is expanding its presence in the Caribbean, adding a new nonstop route between Indianapolis and San Juan, Puerto Rico, Caribbean Journal has learned. The new seasonal service will operate Saturdays from June 4 through Aug. 3, 2026, offering travellers in the Midwest a direct link to the island’s capital. The route adds an […]

Southwest Airlines Is Adding New Nonstop Flights To A Caribbean Island Where Beaches, Boating, and Shopping All Come Together

St. Thomas is the island where beaches sit minutes apart, the harbor stays active from early morning to late evening, and a short ferry ride can turn one vacation into two or three. Magens Bay remains one of the Caribbean’s most photographed beaches. Red Hook continues to anchor the island’s social life with marinas, bars […]

Southwest Airlines Is Adding Flights From Las Vegas to Los Cabos and Puerto Vallarta

Southwest Airlines is expanding its international network this winter with new nonstop service from Las Vegas to two of Mexico’s most popular beach destinations: Los Cabos and Puerto Vallarta. The new routes, launching in June 2026, will give travelers in the western United States more direct access to Mexico’s Pacific coast. Both destinations are known […]

Southwest Airlines Is Coming to St. Maarten, With New Nonstop Flights From Orlando and Baltimore

You know it. It’s one of those iconic Caribbean moments, when the plane makes its final descent into St. Maarten, skimming low over Maho Beach before touching down on one of the Caribbean’s most iconic runways. Beginning April 7, 2026, that moment will belong to Southwest Airlines, too. Southwest has announced it will launch its […]

Southwest Airlines Is Adding a New Nonstop Flight From Nashville to Montego Bay

It may be one of the most instantly recognizable names in Caribbean travel: Montego Bay. From Kokomo to Cocktail, it’s a name that instantly conjures up images of white sand, rum punch and palm trees. And it’s a destination that remains one of the most popular places to visit in the Caribbean, from its vast […]

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 […]

Southwest Airlines Is Launching Two New Daily Nonstop Routes to the US Virgin Islands

It just got even easier to get to the U.S. Virgin Islands. Southwest Airlines has officially confirmed the launch of new daily nonstop flights to St Thomas from two major U.S. gateways: Orlando (MCO) and Baltimore/Washington (BWI). The new service begins early next year, with flights from Orlando starting February 5, 2026, and Baltimore flights taking off February 7, 2026. All flights […]

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