Warm weather destinations to visit using the Southwest Companion Pass


Southwest Airlines is offering its Companion Pass as a sign-up bonus on its credit cards through early February. Here are some great warm weather destinations you can fly to using your pass.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Please review our list of best credit cards, or use our CardMatch™ tool to find cards matched to your needs.

Editor’s Note: The companion pass offer on the Southwest cards mentioned below has expired.

If you live in a cold climate like I do, getting through the winter is rough going.

But it helps if you can break up the winter with a long weekend in a warmer climate or even make plans for a spring vacation that you can dream about during those dreary days.

Right now, Southwest Airlines has the best offer I’ve ever seen to get their coveted Southwest Companion Pass. The Southwest Companion Pass, unlike other airline companion passes, is not a one-time use. Rather, you can bring someone to fly free with you (aside from mandatory government security fees, which in the U.S. are $5.60 per way) for the life of the pass.

Through Feb. 11, 2019 you earn a pass good through the end of 2019 by signing up for any of their three personal credit cards, which include the Southwest Rapid Rewards Priority Credit Card, the Southwest Rapid Rewards Premier Credit Card and the Southwest Rapid Rewards Plus Credit Card, and meeting a $4,000 minimum spend within three months. They’re also throwing in 30,000 Southwest points that you can use to book flights after meeting the minimum spend.

With that in mind, here are five amazing warm weather destinations that you can escape to this winter or spring and take your companion with you on Southwest Airlines for free.

See related: Winter destinations: 4 exotic islands you can visit on points

Grand Cayman

Last year, my family flew to Grand Cayman for spring break for approximately $260 per person, using our Companion Pass. We loved it!

We had 80-degree days all week, enjoyed the ability to just walk to the water nearly anywhere on the island to snorkel, swam with stingrays and couldn’t get enough sunny days on the beach with a tropical drink. Grand Cayman also has a fantastic dining scene with many great affordable restaurants that are also kid-friendly.

You can usually find extremely cheap flights to Grand Cayman from Ft. Lauderdale, Florida, often as low as $59 per way. Keep in mind, however, that mandatory security fees returning to the U.S. are higher and average around $80 per person from the Caribbean.


Hop a Southwest flight to Cuba and bring your favorite companion along to explore this beautiful island before the rest of the world heads there and it becomes overrun with tourism.

One of my GoToTravelGal.com readers, Stephanie Antin of San Diego – who writes the Almost Free Family Travel blog – and her husband visited Cuba via Southwest recently and recommend renting an Airbnb for cheap. She said for a few extra dollars the host will often cook you a full breakfast.

There are many cultural things to experience in Cuba, from exploring architecture to watching a musical performance to meeting local artisans. And there’s plenty of beachgoing and snorkeling, as well.

See related: It’s time to start planning your summer vacation using rewards points

San Diego

One of our favorite destinations, with year-round 70-degree temperatures, is San Diego. If you love the outdoors, get your fill in San Diego with its many beaches, parks and outdoor activities.

When we visited in December (yes, it was still 70 degrees), I took an electric bike tour of the gorgeous La Jolla area, once the home of Theodor Geisel, aka Dr. Seuss, and rode to the top of Mount Soledad for incredible 360-degree views of the area where we could see all the way to Mexico.

There’s also the famous San Diego Zoo and the classic Hotel Del Coronado. And don’t miss a delicious Italian meal in Little Italy.

Costa Rica

Adventure lovers should consider flying to Costa Rica, where activities abound, from zip-lining to spotting wildlife to exploring the rain forest. The country has many national parks, is home to four UNESCO World Heritage Sites and has about 5 percent of the world’s animal species.

Southwest flies into both San Jose and Liberia. You can fly nonstop to San Jose from Houston, the Baltimore/Washington International Airport, or Ft. Lauderdale and from Liberia nonstop from Houston or Baltimore/Washington. Prices are as low as $82 per way. Add a companion for free and you’ve got a heckuva deal!

See related: 10 ways to maximize delayed trip and bag reimbursements

Ft. Lauderdale or Hollywood, Florida

We like this area of Florida as a warm weather and spring break destination. Gone are the days of Ft. Lauderdale packed with teenagers partying til they drop on the beach every April. We like Hollywood Beach, which is known for its “broad” walk that runs alongside the beach and features lots of shops and eateries.

We’ve stayed at both The Diplomat (a Hilton Curio Collection property bookable with Hilton Honors points) and Margaritaville Hollywood Beach resorts and enjoyed both.

You’ll find lots of expansive pools, great options for dining within both properties and access to the beautiful blue waters of the Atlantic. It’s also easy to catch an inexpensive flight out of Ft. Lauderdale even further south to other Southwest destinations like Belize, Jamaica, Turks and Caicos or the Bahamas.

Finally, with a little luck, we may be able to book a Southwest flight to Hawaii sometime this year. The airline says it was in the final stages of approval from the federal government; however, that was put on hold during the recent government shutdown.

I know I’m looking forward to the chance to use my Companion Pass for a flight to Hawaii.

Stay warm out there!

Editorial Disclaimer

The editorial content on this page is based solely on the objective assessment of our writers and is not driven by advertising dollars. It has not been provided or commissioned by the credit card issuers. However, we may receive compensation when you click on links to products from our partners.

Credit Card Rate Report
Cash Back

Questions or comments?

Contact us

Editorial corrections policies

Learn more