When you visit the Caribbean, you’ll quickly recognize that no two islands are alike—though they may all have gorgeous sugar-sand beaches in common. From dancehall beats and reggae vibes to infectious salsa sounds, vibrant communities lure you to their island homes. Enjoy and discover vibrant histories, burgeoning modern urban settings, authentic foods, art unlike anything you’ve encountered before, and, of course, the unparalleled beaches. What are you waiting for? Your flight to the Caribbean is ready to be booked.
Dive into island life with a trip to Montego Bay. Both exotic adventure and luxurious relaxation abound on the island of Jamaica, and Montego Bay has plenty of both to suit every traveler. Dance to the island beat while you pack your bag for your Jamaican vacation.Find flights
Island hopping awaits. Underwater adventures, mountain views, diverse cultural influences, and more are at your fingertips—or just dig your toes into the white sand beaches.
Immaculate beaches and turquoise waters draw people to this idyllic Dutch island, but the friendly residents and vibrant international culture are what keep them coming back.Read more
The largest of the Cayman Islands, this Caribbean paradise provides endless sun and sand.Read more
With Spanish Colonial architecture, vibrant culture, and a wealth of color, Cuba’s capital city is simply unforgettable.Read more
Whether your idea of fun is sitting on a beach with a drink in hand or careening through the rainforest via zip line, this tropical gem has you covered.Read more
Beyond the white-sand beaches lies a thriving food scene, one-of-a-kind hotels, and unforgettable outdoor activities.Read more
Punta Cana is a resort-lover’s dream, where you can luxuriate in sun and surf without lifting a finger.Read more
Combine the historic charm of Old San Juan with the high-end shops of Condado, and throw in sparkling beaches, renowned restaurants, and eclectic hotels. ¡Aqui vamos!Read more
Your bags fly free, because no golf bag4 or swimsuit should be left behind. So pack up without paying up with our two free checked bags.
Think your vacation plans may change? Don’t sweat it. We don’t charge you fees to change your mind2.
Surf the Web before you surf the waves with gate-to-gate WiFi on your flight. Bring your device, and the Internet will make time fly by on our flights to tropical destinations.
Southwest seats give you up to a 31-inch pitch, 17-inch width, and 2-inch recline, which all adds up to a more comfortable flight on our 737-700 aircraft.
Boredom doesn’t fly with us. So on your flight, watch a movie5 for free. Just one way we make getting to your tropical destination as nice as being there. Well...almost.
Southwest is bringing our low fares and no hidden fees with us. We want to make your trip special, so we’re taking everything you love about Southwest and bringing it all to your favorite destinations. Get everything Transfarency has to offer on your next trip, only with Southwest.
Southwest Rapid Rewards® lets you use your points on any flight, any day, any time, which means you can turn your points into a reward flight. Sign up and see why we’ve been named the best rewards program four years in a row6. Points that actually reward you with getaways, that’s Southwest Rapid Rewards.Sign up now
You can use your points to book any seat, on any flight, no exceptions. Any day, any time, any flight, your points are ready to take you to paradise.
If there’s a seat available on a Southwest flight, you can use your points. It’s that easy. So no matter when you want to get away, you can use your points to get you there. As long as we have a spot available on a flight, you can book it with your Southwest Rapid Rewards® points.
No matter when you earn them, they’ll be there for you to redeem on your flight to our tropical destinations or anywhere else you want to go.
You can earn points on flights and on everyday purchases with our partners, which makes getting to our tropical destinations easy. And our reward flights are based on our low fares, so the lower the fare, the fewer points you have to use. It’s almost like we want you to have the vacation of a lifetime.
If you’re new around here, we’re so happy to have you. Flying with us is easy and fun—this guide is your one-stop shop for doing things the Southwest way.
We’ll be waiting to welcome you with free snacks and countless smiles, so we want to get you onboard as quickly and smoothly as possible!
Our tropical destinations have country-specific travel policies and restrictions unique to the destination. Here's a list of documentation required to check out before booking and traveling.
The check-in process is a little bit different for international travel. Learn more here.
Save time at U.S. Customs and Passport control checkpoints when you download the Mobile Passport app by Airside Mobile (available in select cities).
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Our tropical destinations have country-specific travel policies and restrictions unique to the destination. Here's a list of documentation required to check out before booking and traveling.
4A golf bag can be substituted for one checked bag.
5Download the Southwest app to view movies and on-demand content. Inflight messaging only allows access to iMessage and WhatsApp. Apps must be downloaded before the flight. Internet access for $8 a day per device on WiFi-enabled aircraft. Price is subject to change. May not be available for the full duration of flight. Prohibits access to high-bandwidth applications and websites, including Netflix, HBO GO® and VoIP, along with certain obscene/offensive content.
62016-2019 Freddie Awards.
7As reported in the CarTrawler Reward Seat Availability Survey, May 16, 2019, and Switchfly Reward Seat Availability Surveys 2010 – 2019, at IdeaWorksCompany.com.