Top 7 Southwest International Destinations for Families

Jan 12, 2019

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It is no wonder Southwest is TPG‘s No. 1 airline for families. Southwest offers flexible change and cancellation policies, makes using your points easy, allows for family boarding and you can check two bags for free (and bring a full-sized carry-on). On top of that, Southwest will actually fly your family to some awesome international destinations. True, the airline might not offer flights to see castles in Europe, scuba dive the Great Barrier Reef in Australia or go on safari in Africa, but if you are in the market for a pretty sweet beach destination outside of the US, Southwest can probably take you there. In fact, the airline flies to 14 international destinations throughout the Caribbean, Mexico and Central America.

Southwest Airlines will allow you to experience the crystal blue waters of the Caribbean (Photo courtesy of Jennifer Yellin /
Southwest Airlines will allow you to experience the crystal blue waters of the Caribbean. (Photo courtesy of Jennifer Yellin /

The best part about Southwest Airlines is that it makes it incredibly easy for a family member to fly with you for free. Yes, free (other than taxes). If you’ve never heard of the Southwest Companion Pass, now is the time to pay attention.

You can use the bonus points earned from the Southwest credit cards to earn the Companion Pass. The eligible cards include: the Southwest Rapid Rewards Plus Credit Card, the Southwest Rapid Rewards Premier Credit Card and Southwest Rapid Rewards Priority Credit Card.

Once you get approved for a Southwest credit card that will help you earn the 110,000 points needed in a calendar year to trigger a Companion Pass, you can start dreaming about where it will take you. I’ve had the Southwest Companion Pass for 11 years and here are my personal favorite family-friendly international destinations where you can fly Southwest Airlines.


Aruba is quite possibly one of my favorite family-friendly Caribbean islands. The water is calm and crystal clear, the beach is long and wide, there are a ton of point redemption hotel opportunities and you’ll find many kid-friendly activities throughout the island. The weather is also almost always perfect, and since the island is outside of the hurricane belt, it is a very popular destination to visit in the summer and fall. I personally love that Aruba is safe, which allows families to feel comfortable taking their kids away from the resort and explore the rest of the island.

Image courtesy of Holiday Inn Resort Aruba
Image courtesy of Holiday Inn Resort Aruba

I’ve already taken my now 5 year old daughter to Aruba twice: once when she was 18 months and again when she was 2.5 years old. Out of all of our (many) beach vacations, my husband and I still talk about how much we love Aruba for a family vacation.

Fly Into: Aruba (AUA) with nonstop flights from Houston (HOU), Fort Lauderdale (FLL) and Baltimore (BWI) on Southwest.

Adventure off road Aruba
Take your family on an off-roading adventure in Aruba to see some incredible views. (Image courtesy of 2DadsWithBaggage)


The Bahamas is a great option for a family-friendly vacation, especially since Baha Mar opened its doors. Within the complex, you have the Rosewood, SLS and, of course, the Grand Hyatt, which is probably the best option if you are traveling with your kids (and want to use points). And, you still have the Atlantis on Paradise Island, which I used to dream about while growing up. Being able to slide through a shark tank is definitely on the “wow” factor for every single child!

Photo courtesy of Atlantis
Photo courtesy of Atlantis

I personally love how close the Bahamas is to the US mainland as it makes for a short and easy flight, especially for those coming from the East Coast. Spending the least amount of time in an airplane with kids as possible is ideal, especially for a long weekend type of getaway. Southwest prices to Nassau are usually very favorable and that’s something to consider when you are purchasing plane tickets for an entire family. I personally just flew my family of four to Nassau and spent around 18,000 Southwest Rapid Rewards points per ticket round-trip coming from Boston! And although we are a family of four, I only had to purchase three tickets as my daughter was my companion due to having the Southwest Companion Pass.

Fly Into: Nassau (NAS), with nonstop flights from Fort Lauderdale (FLL) and Baltimore (BWI) on Southwest.

Cayman Islands

Grand Cayman, known for its picture-perfect Seven Mile Beach, is an ideal destination for families looking for a relaxing beach getaway. Here you’ll find soft white sand, crystal clear waters and many kid-friendly activities throughout the island. And if you haven’t heard about Stingray City, this is a must-do adventure during your visit. There are not too many places where you can actually swim with stingrays, but Grand Cayman has you covered.

For those looking to redeem their hotel points for a free night stay, Grand Cayman is the perfect place. It has everything from budget-conscious to high-end luxury and everything in between. The Westin Grand Cayman is currently on my radar, and I love that I can get there by using my Marriott Rewards points for the stay, combined with Southwest points and the Companion Pass for flights.

Fly Into: Grand Cayman (GCM), with nonstop flights from Fort Lauderdale (FLL), Houston (HOU) and Baltimore (BWI) on Southwest.

Ready for fun on Seven Mile Beach (Summer Hull / The Points Guy)

Costa Rica

Costa Rica is perfect for those seeking some variety in their vacation — you can start with the Arenal Volcano, and then head to the rainforest and finish by surfing at the beach. Don’t miss the thrill-seeking activities of whitewater rafting and zip-lining along the way. In my opinion, Costa Rica is a better suited vacation for families who are past the baby and toddler stage, although you can still just relax and get pampered in some great resorts with younger kids.

For those looking to use their hotel points, the Andaz Costa Rica in Papagayo will give you the biggest bang for your buck. At only a Category 4 property costing 15,000 World of Hyatt points a night (increasing to a Category 5 in March 2019) this hotel provides an amazing not-to-be-missed value. Not to mention, the kids club there is absolutely free for kids four and up. Until it becomes a Category 5 property, you can also use a Category 1–4 Hyatt award from the World of Hyatt Credit Card.

Andaz Costa Rica (Summer Hull / The Points Guy)
Andaz Costa Rica (Summer Hull / The Points Guy)

If you are looking to fly Southwest, know that it actually flies into two airports: San Jose and Liberia. This allows you to start your vacation in one area and then travel around the country departing from another area, if desired.

Fly Into: 

  • Liberia (LIR), with nonstop flights from Baltimore (BWI) and Houston (HOU) on Southwest.
  • San Jose (SJO), with nonstop flights from Baltimore (BWI), Houston (HOU) and Ft. Lauderdale (FLL) on Southwest.
The striking blue Rio Celeste is one of Costa Rica's best-kept secrets.
The striking blue Rio Celeste is one of Costa Rica’s best-kept secrets.

Dominican Republic

If you are looking for an all-inclusive for your family, the Dominican Republic is the place to be. Vacationing to there with your family is easy as it is one of those places where you do not really have to leave the resort. Instead, just relax at the pool and beach. There are many kids club opportunities and, typically, nightly entertainment. I cannot wait for the Hyatt Ziva and Hyatt Zilara to eventually open in Punta Cana. Until then, check out all-inclusives, such as the Viva Wyndham Dominicus Beach, for just 15,000 Wyndham Rewards points per night.

The Westin Punta Cana is not all-inclusive, but can be booked for just 35,000 Marriott Rewards points per night. This opens up the ability to use a Marriott 35k certificate from cards like the Starwood Preferred Guest® Credit Card from American Express or Marriott Rewards Premier Plus Credit Card.

Just keep in mind that Southwest only flies to Punta Cana within the Dominican. It is a fairly large country with many different resort areas, so make sure to plan your hotel(s) accordingly. On a side note, the Punta Cana Airport will also allow you to swim outside while overlooking the airport operations if you have Priority Pass. This is a great way to keep your kids occupied while waiting at the airport. I have an upcoming trip planned to Punta Cana and cannot wait to check this out with my kids. And, of course, I am flying Southwest with my Companion Pass.

Fly Into: Punta Cana, with nonstop flights from Baltimore (BWI), Chicago (MDW), St. Louis (STL), Atlanta (ATL) and Houston (HOU) on Southwest.

Playa Blanca, Punta Cana, Dominican Republic, Caribbean Sea.
Playa Blanca, Punta Cana, Dominican Republic.


Southwest actually flies to four destinations in Mexico — Cabo, Puerto Vallarta, Mexico City and Cancun. Getting to Mexico is actually quite easy on Southwest as it serves many destinations throughout the US and has a ton of nonstop flights, which is great for families. For the most part, there are many departure options 365 days a year. Some of the other destinations on this list run on a more seasonal schedule, giving you some limitations, but with Mexico, the options are pretty endless.

While Mexico City doesn’t really fit the bill as a beach-friendly destination, if you are looking for a more “city” vacation for your family, this is a good opportunity to experience the Mexican culture. You then have Cabo and Puerto Vallarta on the West Coast of the country and Cancun on the East Coast of the country making a Mexican vacation possible for every family throughout the US. (Here are the best times to visit Mexico.)

Mexico can even be more economical than many of the Caribbean destinations served by Southwest listed here. There are a ton of all-inclusive opportunities and that’s ideal so you don’t have to constantly open your wallet for food or shell out top dollars for your children to enjoy a kid club.

Hyatt Ziva Cancun Kid Club
Hyatt Ziva Cancun Kid Club (Summer Hull / The Points Guy)

Fly Into: 

  • Cabo San Lucas (SJD), with nonstop flights from Houston (HOU), Austin (AUS), Baltimore (BWI), Chicago (MWD), Denver (DEN), Sacramento (SMF), Oakland (OAK), San Jose (SJC), Los Angeles (LAX), Orange County/Santa Ana (SNA) and San Diego (SAN).
  • Puerto Vallarta (PVR), with nonstop flights from Houston (HOU), Denver (DEN), Oakland (OAK), Los Angeles (LAX) and San Diego (SAN).
  • Cancun (CUN), with nonstop flights from Ft. Lauderdale (FLL), Raleigh-Durham (RDU), Baltimore (BWI), Pittsburgh (PIT), Columbus (CMH), Atlanta (ATL), Milwaukee (MKW), Chicago (MDW), Indianapolis (IND), Nashville (BNA), St. Louis (STL), New Orleans (MSY), Denver (DEN), Austin (AUS), Houston (HOU), San Antonio (SAT) and Los Angeles (LAX).
  • Mexico City (MEX), with nonstop flights from Houston (HOU).
An empty beach in Cancun, Mexico. (Photo via Shutterstock)
An empty beach in Cancun, Mexico. (Photo via Shutterstock)

Turks and Caicos Islands

Turks and Caicos is one of those islands that has it all — white sandy beaches, amazing restaurants, lots of adventure and a great nightlife. And while this destination might be high on your list for a relaxing beach getaway, there is probably one reason you have yet to visit: It is incredibly expensive! There are many luxurious and family-friendly hotels throughout the island, but you’ll have to dig deep into your pocket to afford them. Fortunately though, there are plans for the Andaz Turks and Caicos to open in 2021, which will allow families to use their hard-earned Hyatt points for an award stay. Fingers crossed everything goes as planned. In the meantime, you can still use your Capital One® Venture® Rewards Credit Card to get 10x points per dollar by booking at, or your Citi Prestige for your 4th night free as this is still an island not to be missed.

Fly Into: Providenciales (PLS), with daily nonstop flights from Fort Lauderdale (FLL) on Southwest.

Sipping cocktails from a coconut is an absolute must in Turks & Caicos.
Sipping cocktails from a coconut is an absolute must in Turks & Caicos.

Bottom Line

The Southwest Companion Pass will easily allow your family to experience some amazing international destinations at quite a discount. Having the Southwest Companion Pass for the past 11 years has opened up travel to us in ways we couldn’t have otherwise experienced. It has allowed my family to save thousands and thousands of dollars throughout the years.

Jennifer Yellin covers family travel deals for TPG and blogs at Deals We Like. Follow her family’s adventures on Twitter and Instagram.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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