8 cool places you didn’t know you could fly on Southwest

Feb 27, 2021

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Yes, it is true Southwest Airlines won’t take you to some exotic destinations like Bora Bora or Tahiti — or even a hop over the pond to Europe. But that doesn’t mean the airline only flies to Vegas and Orlando (although, they totally do). Southwest Airflines also offers some pretty cool destinations just within the U.S., Mexico and even the Caribbean.

So if you are looking to explore the nooks and crannies of a domestic (or a nearby international) destination, don’t overlook Southwest.

On top of flying to some cool spots, this family-friendly airline also has flexible change and cancellation policies, enables you to check two bags for free — and let’s not forget the BOGO opportunity with the Companion Pass. With the Southwest Companion Pass, another passenger can fly with you for free during the life of the pass. Yes, you read that correctly, free (plus taxes and fees) to any destination that Southwest flies.

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(Photo by David McNew/Getty Images)

Right now, you can earn the Companion Pass with the welcome offer on the Southwest Rapid Rewards Premier Credit Card, Southwest Rapid Rewards Priority Credit Card and Southwest Rapid Rewards Plus Credit Card without having to earn the necessary tier qualifying points. All three cards are offering a Companion Pass valid through Feb. 28, 2022,  plus 30,000 Rapid Rewards points after you spend $5,000 on purchases in the first three months of account opening.

Related: How to use the Southwest Companion Pass

So with your Companion Pass (almost) in hand, consider these places for your next vacation:

Telluride, Colorado

Planning on skiing Telluride this winter or next? If so, Southwest’s brand-new service to Montrose (MTJ) will put you just an hour and a half from the mountain. The airline offers nonstop flights from both Dallas (DAL) and Denver (DEN), and while the Denver flight operates three flights a day, seven days a week, the flight from Dallas operates just on Saturdays.

And with Telluride now on the Epic Pass, if you have a pass that includes Telluride access, this is the perfect opportunity to not only use points for your flight — and even fly BOGO with the Companion Pass— but to also have your lift tickets already paid for.

Related: Top 10 things to do in Telluride

(Photo by DOUGBERRY/Getty Images)

If you make the trip we really recommend staying at the charming Dunton Town House one block from the gondola. This is now a Mr & Mrs Smith property, so you can theoretically use IHG points when available, though we didn’t spot availability in our searches.

The Fairmont Heritage Place, Franz Klammer Lodge using Accor points is another option. You might find an even more reasonable boutique hotel or inn by using your Chase Ultimate Rewards points.

Unfortunately though, if you are looking to enjoy Telluride over the summer, Southwest won’t take you there as this service is seasonal, but for those looking for an amazing ski resort town, being able to access Telluride more easily is a big win for Southwest flyers.

Fly into: Montrose (MTJ) with nonstop flights from Dallas (DAL) and Denver (DEN).

Steamboat Springs, Colorado

Similar to Montrose, Steamboat Springs (HDN) was also just added to Southwest’s route map as a seasonal service during the winter months. This gives travelers another opportunity to enjoy the mountains, especially those looking to ski at Steamboat. And with multiple flight options from Denver and the airport only 30 minutes away from the mountain, some passengers will be able to hit the slopes just after noon (flights from Dallas only operate on Saturdays).

Related: 5 reasons to ski at Steamboat Springs this year

Steamboat Springs. (Photo by Zach Shortway/Getty Images)

Best of all, Steamboat is on the Ikon Pass and those passholders know that they fully plan their trips around ski resorts on the pass. So for those with an Ikon Pass already in hand — or those looking to purchase the pass for next year — you now have one more way to fly into Steamboat.

Steamboat also offers more in the way of points hotels than what you’ll find at Telluride. Whether you have Hilton, Marriott, IHG or Wyndham points, there is a property you can stay at with your hard-earned points. We like the Sheraton right at the base of the mountain and sometimes bookable with a Marriott 35K certificate.

Fly into: Steamboat Springs (HDN) with nonstop flights from Dallas (DAL) and Denver (DEN).

Savannah, Georgia, or Hilton Head, South Carolina

If you are looking for some Southern charm or to relax by the beach, Southwest is adding Savannah/Hilton Head (SAV) to the route map on March 11, 2021. Since Savannah and Hilton Head are located only 45 minutes from one another, the airport easily allows you to visit either destination — or both.

As Georgia’s oldest city, Savannah is filled with with a ton of history and culture. There are many historic tours you can take, such as the Flannery O’Connor Childhood Home or the American Prohibition Museum, and you can even embark on a hop-on/hop-off or riverboat tour. And the walking ghost tours are something not to be missed.

And if you are into the food scene, Savannah is well known for eating and drinking. From renowned restaurants to various walking food tours, you’ll be well fed (and hydrated). In fact, in the historic district it’s even legal to carry an open container of alcohol.

Related: Maximizing points and miles on a trip to Savannah, Georgia

A Southern manor located in the downtown historic district of Savannah, Georgia, stands proudly among the old oak trees. (Photo by Getty Images)

Or, if you prefer the beach, head to Hilton Head Island, which offers 12 miles of beach on the Atlantic Ocean. While Hilton Head is a golfer’s delight, there is also a ton to do off the course. From boat rentals to stand-up paddleboarding, there are plenty of beach and water activities to soak up the sun.

Related: 7 reasons why your next vacation should be on Hilton Head Island

There are also a ton of resorts, many which allow you to use your hotel points. The Marriott Hilton Head is a great option as it is a category hotel which means it only requires 35,000 points during their standard rate. This means you can use an award certificate that comes with the Marriott Bonvoy Boundless Credit Card and Marriott Bonvoy Business™ American Express® Card.

(Photo courtesy of HIlton Head Island)

Fly into: Savannah/Hilton Head (SAV) with nonstop flights from Nashville (BNA), Baltimore (BWI), Dallas (DAL), Houston (HOU) and Chicago (MDW).

Sarasota, Florida

Sarasota (SRQ) is another recent addition to the Southwest route map, which means you no longer have to fly into Tampa and drive an hour to visit this great destination.

This low-key Florida beach town on the Gulf Coast has a ton to offer, especially Siesta Key Beach. With white sand and crystal-clear water, Siesta Key Beach is one of the most beautiful beaches I’ve ever seen. Parking and beach access is complimentary, and the playground is a big hit with kids. If you are a beach lover, Siesta Key is a bucket list beach to visit.

(Photo by Zhukova Valentyna/Shutterstock)

Aside from the beach, Sarasota also has a huge cultural presence. From operas and symphonies to the Ringling Circus Museum, there is so much to do and see. And of course St. Armands Circle can’t be missed with its upscale shopping and many restaurants.

Sarasota, Florida. (Photo by John Coletti/Getty Images)

And with Sarasota being just two hours from Disney, it is the perfect destination to pair with a Disney vacation.

Fly into: Sarasota (SRQ) with nonstop flights from Atlanta (ATL), Nashville (BNA), Baltimore (BWI), Columbus (CMH), Houston (HOU), Indianapolis (IND), Chicago (MDW), Milwaukee (MKE) and Pittsburgh (PIT).

Santa Barbara, California

Looking for a trip to California, but want to avoid the major cities? You can now easily visit Santa Barbara (SBA) with Southwest Airlines starting April 12, 2021. Santa Barbara is an incredibly cute beach town right on the Pacific Ocean, but without the hustle and bustle of Los Angeles. With many beaches to visit and a variety of beach activities, this is the perfect place to get away and relax.

Related: Here’s where to look for fun family activities in Santa Barbara

Beach aside, there is also the Santa Barbara Zoo, the Museum of Natural History, the Santa Barbara County Courthouse and tons of parks with many bike paths. You can also venture outside of Santa Barbara for the day and visit many wineries in Santa Ynez Valley and Santa Maria Valley.

paddleboarders Santa Barbara Stearns Wharf
From Stearns Wharf in Santa Barbara, you can watch boats, surfers and paddleboarders glide by. (Photo by Jon Bailey)

Santa Barbara also offers many hotel opportunities to use your points, such as the Hilton Santa Barbara Beachfront Resort, The Ritz-Carlton Bacara, the Hotel Indigo Santa Barbara and the Mar Monte Hotel. The Mar Monte Hotel is part of Hyatt’s Unbound Collection and is currently priced as a Category 4 property, making it a perfect opportunity to use your Category 1-4 free night certificates from the World of Hyatt Credit Card (although this property is set to increase to a Category 5 property in March, so make sure to secure your reservations now).

Of course if you are looking for a longer vacation within California, you can easily couple a Santa Barbara vacation with Los Angeles to the south or San Francisco to the north. And since Southwest services those destinations as well, you can easily fly into one airport and out of the other to really see as much as possible of the Pacific Coast Highway.

Fly into: Santa Barbara (SBA) with nonstop flights from Denver (DEN), Las Vegas (LAS) and Oakland (OAK).

Portland, Maine

If you are looking for some New England charm, Portland has you covered.

This quaint seaside destination is truly a special place to visit 12 months a year. While the summer months will provide you with better weather and more beach activities (Scarborough Beach is 20 minutes away and Kennebunkport is 35 minutes away), those looking for a leaf-popping destination will love the fall colors. But if you really want to stay away from tourists, the winter and spring still have a lot to offer with many restaurants and bars. And do not miss the many breweries.

(Photo by Kenneth C. Zirkel/Getty Images)

Of course a visit to Portland isn’t complete without a ferry ride to Peaks Island (more popular during the summer and early fall). You can rent a golf cart for the day to truly explore the island and then end the day with some amazing New England lobster.

Portland is one of my family’s favorite destinations within New England for a weekend getaway since there is so much to do and see. Whether you are looking for an adults-only trip or a place to bring the kids, a visit to Portland should be high on everyone’s list.

Fly into: Portland (PWM) with nonstop flights from Baltimore (BWI).

Colorado Springs, Colorado

Bypass Denver and head straight to Colorado Springs. While only 85 miles away, you are right in the middle of some amazing outdoor adventures. Whether you are visiting for just the weekend or the month, there is truly something for everyone. Here you can go hiking, whitewater rafting or even hang from a zip line. The less-adventurous will also appreciate the history and arts.

This is a brand-new destination to Southwest where you can start flying from March 11, 2021, onward. The airport is less than 20 minutes to downtown, or stay in a more luxury atmosphere at the famous Broadmoor resort.

Fly into: Colorado Springs (COS), with nonstop flights from Dallas (DAL), Denver (DEN), Las Vegas (LAS), Chicago (MDW) and Phoenix (PHX).

Cozumel, Mexico

Looking to enjoy the beaches of Mexico, but want to get away from the ultra-touristy areas of Cancun?

Instead, Southwest can take you directly to Cozumel (CZM). You’ll still have your fair share of tourists, but with most cruises on hold for now, it shouldn’t be as overrun as it once was. And if you’ve already been to Cancun, now might be the perfect time to explore another area on the east coast of Mexico.

Cozumel is also a diver’s paradise. Since Cozumel has smaller and rockier beaches, it has some great coral reefs, which make for some amazing snorkeling and diving opportunities.

Related: Top 9 Southwest international destinations for families

People snorkeling at Chankanaab National Park. (Photo by Wolfgang Kaehler/LightRocket via Getty Images)

And if you are looking to use your points for a beachfront vacation, the Westin Cozumel is just a Category 5 property, which requires between 27,000 and 40,000 points per night. Or, you can use your 35,000-point award night certificate that comes with the Marriott Bonvoy Business American Express Card and Marriott Bonvoy Boundless Credit Card.

Fly into: Cozumel (CZM) with nonstop flights from Houston (HOU).

Bottom line

With so much of the U.S. to explore, Southwest will take you to some unique destinations. And best of all, you can always fly buy one, get one, as long as you are a Southwest Companion Pass holder. With the current card offers, earning the pass is easier than ever before. I’m personally going on my 13th year as a passholder and it truly has allowed my family to visit more of the U.S., Canada and the Caribbean at a significant cost savings.

Featured photo by Blaine Harrington III/Getty Images.

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