Whether you're craving an under-the-sea scuba adventure amongst coral reefs, to traverse the remains of indigenous civilizations, or to take in the best of everything a modern city with ancient roots has to offer, you'll find a flight to your next adventure with us. Explore some of our most popular international destinations in Mexico, Central America, and the Caribbean.
Add exploring the Walled City of the Island of Enchantment to the itinerary of your next tropical vacation—visit San Juan. See how old-world relics mingle with modern-era amenities in this culturally rich capital city, but don’t forget to spend plenty of time having fun in the sun.Find flights
It doesn’t matter if you're planning to soak up the sun and surf or dive into urban nightlife, visiting Mexico with Southwest is as easy as saying ¡Hola!
Backpacking opportunities and beaches abound on the Central American subcontinent—so do rich cultural experiences, ancient landmarks, and so much more.
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.
Your bags fly free2, because no golf bag3 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 mind4.
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 737-800 aircraft.
Boredom doesn’t fly with us. So on your flight, watch a blockbuster, or catch up on your favorite shows 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 new favorite islands. 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 island getaways, that’s Southwest Rapid Rewards.Sign up now
Plus, earn 5 points per $1 spent on Southwest® travel purchases.** An offer too massive to miss.
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 & 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).