4 Fantastic Winter Travel Destinations for Families to Visit on Southwest

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Lyn writes about how to fly free on Southwest on her GotoTravelGal.com blog.  And wrote a free guide on how to earn the coveted Southwest Companion Pass that lets 1 person fly nearly free with you for up to 2 years.  I’ve asked her to share some fun winter travel destinations for families and how you can get there on Southwest.

Lyn:   We largely fly free around the US and are amazed at how many great – and varied – places there are to visit in our country.  We love to fly Southwest, because we can each check 2 bags, there are no change or cancellation fees, and we can book any flight any time so long as we have the points.  

There are NO blackout dates on Southwest.  As long as a seat is for sale, you can use points to book it!

4 Fantastic Winter Travel Destinations For Families To Visit On Southwest
San Diego Is One of Our Favorite Cities to Visit Year-Round!

Whether you’re looking for a warm getaway this winter, or in search of snow, here are some of our favorite options.  You can reach them by flying directly to the city on Southwest, or to a city within an hour or so of the destination.

1.   San Diego

Link:   Use Southwest Points to Save Money on a Family Trip to San Diego

San Diego is one of my family’s favorite US cities to visit.  The weather is perfect (averaging the mid-70s year round), there are lots of beaches, and tons of family-friendly outdoor activities.  We even headed to the city this summer to experience Comic Con for the first time!

4 Fantastic Winter Travel Destinations For Families To Visit On Southwest
We Got a Kick out of Getting Close to the Sea Lions and Watching Their Antics in La Jolla

Here are some of our top recommendations for things to do in San Diego:

2.   Colorado Springs

If you love the outdoors – and gorgeous scenery – Colorado Springs is fantastic option for families.  With more than 300 days of sun each year, even a cool winter day seems perfect with snow blanketing the Rocky Mountains, Pikes Peak, and the lovely landscape.

4 Fantastic Winter Travel Destinations For Families To Visit On Southwest
One of the Many Awesome Things to Do in Colorado Springs Is to Hike the Garden of the Gods

To visit Colorado Springs on Southwest, you’ll need to fly to Denver, and drive south (or take a shuttle) to Colorado Springs – about 70 miles.

If you want to ski, there are resorts within a couple hours, but its mild winter temperatures averaging from the low 30s to upper 40s make it a great climate to get outdoors and enjoy the scenery all year.

Here are some of our favorite things to do in Colorado Springs:

3.   Myrtle Beach

While Southwest does not fly directly into Myrtle Beach, they do fly to Charleston, which is only 95 miles south and also a great city!  We used to live in Charleston and would drive to Myrtle Beach for the day often, because there are so many attractions.

4 Fantastic Winter Travel Destinations For Families To Visit On Southwest
Enjoy Sunshine, Miles of Beaches, and Plentiful Activities in Myrtle Beach

Also with a mild winter climate and many days of Carolina sunshine (with even a few days in the 70s!), Myrtle Beach offers miles of beaches and tons of activities to keep everyone entertained.

Some fun things to do in Myrtle Beach:

  • Play at your hotel!  Most Myrtle Beach hotels have indoor waterparks, lazy rivers, multiple pools, jacuzzis, and more – perfect for cooler winter days
  • Walk the beach.  Bring a metal detector to look for lost jewelry and coins or search for shells
  • Visit Broadway at the Beach, a large entertainment district with shopping, dining, and lots of attractions
  • Pet stingrays at Ripley’s Aquarium
  • Get a fun lesson in science at WonderWorks, which you will know because it “looks” like an upside down house from the outside
  • Ride the Myrtle Beach SkyWheel, which is the highest observation point of the Atlantic in North America
  • Play a round of mini golf, which are a dime a dozen in Myrtle Beach with every theme under the sun
  • Walk the boardwalk.  You’ll love the people-watching, dozens of arcades, and ocean views
  • Find a bargain.  The Grand Strand has several top outlet malls including Tanger Outlets with more than 200 brands

4.   Beaver Creek

My family has owned a condo in Beaver Creek since the 1980s.  And it’s one of our favorite places to visit both winter and summer.  You’ll need to fly into Denver to reach Beaver Creek Resort, which is about 100 miles west.  And then rent a car or hop on the Colorado Mountain Express, which takes you to the village.

4 Fantastic Winter Travel Destinations For Families To Visit On Southwest
Beaver Creek Is a Beautiful Spot in the Rocky Mountains to Enjoy Skiing and All Things Winter

Beaver Creek is very close to Vail, but much quieter.  You’ll find shorter lines and less crowded terrain.

Here are some of our favorite things to do in Beaver Creek, Colorado:

  • Ski, ski, and ski some more.  Take kids to the new Red Buffalo Park ski area, which offers fun features like snow sculptures and fun things to ski through
  • Take a sleigh ride to dinner in the mountains at Allie’s Cabin
  • Go snowmobiling and look for wildlife like elk and deer
  • Enjoy fresh chocolate chip cookies on the mountain and in the village daily – free
  • See a show at the Vilar Performing Arts Center
  • Go ice skating at the rink in Beaver Creek Village
  • Enjoy pizza at Blue Moose Pizza
  • Grab a yummy gelato at Rimini in the village
  • Snuggle by the fire in your hotel or condo, and play a board game while the snow falls out your window
  • Enjoy an Italian dinner at Toscanini while the kids play on Etch-a-Sketches before your meal

Remember, even if Southwest does not fly directly out of your home airport, they may fly out of an airport nearby.  For example, although Southwest flies out of Indianapolis, our home airport, we sometimes drive ~2.5 hours north to Chicago-Midway to take advantage of lower fares.  Here’s Southwest’s route map to check where they fly!

Collecting Southwest Points for Your Trip

The quickest way to collect Southwest points for your flight is to sign-up for 1 or more of the Chase Southwest cardsboth personal and business, and earn the sign-up bonus.

Or, you can sign-up for a credit card that earns Chase Ultimate Rewards points, including the Chase Sapphire Preferred® Card, Ink Business Preferred℠ Credit Card, and Chase Sapphire Reserve, and earn the sign-up bonus after meeting the minimum spending requirements.  These points, which you can continue to earn through spending on the card, also transfer instantly to Southwest at a 1:1 ratio.

Bottom Line

Southwest has wonderful destinations you can reach this winter with plenty of family-friendly activities.  Choose from beaches or snow-covered mountains to visit:

Put your Southwest points to use for a family award trip with NO blackout dates.  And don’t forget you can transfer Chase Ultimate Rewards points to Southwest, too!

Million Mile Secrets features a team of points and miles experts who have traveled to over 80 countries and have used 60+ credit cards responsibly to accumulate loyalty points and travel the world on the cheap! The Million Mile Secrets team has been featured on The Points Guy, TIME, Yahoo Finance and many other leading points & miles media outlets.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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