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

Oct. 19, 2021
15 min read
Main Street (West Colorado Avenue), Telluride, Colorado USA.
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Yes, it is true Southwest Airlines won't take you to some exotic destinations like Bora Bora or Fiji — or even on a hop over the Pond to Europe. But that doesn't mean the airline only flies to Las Vegas and Orlando (although, they totally do). If you haven't checked the airline's route map in a while, Southwest Airlines offers some pretty cool destinations within the U.S., Mexico, the Caribbean and even Central America.

So, if you are looking to explore the nooks and crannies of a domestic (or a nearby international) destination, don't overlook Southwest and its no-fuss approach to travel.

On top of flying to some interesting locales, 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 Companion Pass. With the Southwest Companion Pass, another passenger can fly with you for nearly free (you just have to pay the taxes and fees on their ticket) during the life of the pass.

Yes, you read that correctly, free (plus taxes and fees) to any destination that Southwest flies, including some of these under-the-radar spots.

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(Photo by David McNew/Getty Images)

Speaking of the Companion Pass, right now, you can come pretty close to earning it with the welcome offers on the Southwest Rapid Rewards Premier Credit Card, Southwest Rapid Rewards Priority Credit Card and Southwest Rapid Rewards Plus Credit Card. With any of these three cards, you can earn up to 100,000 points — 50,000 points after you spend $2,000 in three months, plus an additional 50,000 points after you spend $12,000 in 12 months from account opening.

This means the points earned from the welcome offer and the minimum spend requirement combined will net you at least 112,000 Companion Pass-qualifying points. To earn the Companion Pass, you need to earn 125,000 Companion Pass qualifying points in a calendar year, so you'd only be 13,000 points off from doing so at most.

If you wait to earn both tiers of the bonus in 2022, you'd be within reach of earning the Companion Pass through the end of 2023. You can then earn the remaining points required by flying Southwest, spending on a Southwest credit card, using the Southwest shopping portal and more.

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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? If so, Southwest's relatively 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). The Denver flight operates daily while the Dallas flight operates less frequently.

And with Telluride 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 book with IHG points if you find availability.

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 has traditionally been seasonal. 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 recently 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 frequencies from Denver and the airport only 30 minutes away from the mountain, some passengers may 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)

Steamboat is on the Ikon Pass. Those with a pass already in hand -- or those looking to purchase the pass for this season -- 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.

One of our favorite hotel options is the Sheraton Steamboat Resort Villas that's right at the base of the mountain. It's a Category 5 property, so you can use a Marriott 35,000-point certificate to book it during standard and off-peak dates.

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, flying into Savannah/Hilton Head (SAV) can get you just that sort of getaway. 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 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. Plus, walking ghost tours are 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 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 a ton to do off the course. From boat rentals to stand-up paddleboarding, you'll have no problem finding an opportunity 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 of which allow you to use your hotel points. The Marriott Hilton Head is a great option as it is a Category 5 hotel, so it only requires 35,000 points per night during on standard dates. 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 World, it is the perfect destination to pair with a Disney vacation.

Fly into: Sarasota (SRQ) with nonstop flights from Atlanta (ATL), Nashville (BNA), Dallas (DAL), St. Louis (STL), Baltimore (BWI), Columbus (CMH), Houston (HOU), Indianapolis (IND), Chicago (MDW) 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. Santa Barbara is an incredibly cute beach town right on the Pacific Ocean but without the hustle and bustle of Los Angeles. It's an excellent relaxation destination with numerous beaches and associated activities.

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 and 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.

Heading up the Gibraltar Road in Santa Barbara, California. (Photo by Just Paget/Getty Images)

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, which is part of Hyatt's Unbound Collection.

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 see as much of the Pacific Coast Highway as possible.

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, Maine 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 beach time (Scarborough Beach is 20 minutes away and Kennebunkport is 35 minutes away), those looking for a leaf-peeping 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 incredible restaurants, bars and 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 explore the island, and end the day with some tantalizing New England lobster.

Portland is one of my family's favorite destinations within New England for a weekend getaway. 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) and Chicago (MDW).

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. 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, art and food scenes.

You'll find two Category 2 Hyatt Place properties in Colorado Springs — one downtown and one near Garden of The Gods.

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, especially as cruise ships return, but 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/Getty Images)

And if you are looking to use your points for a beachfront vacation, the Westin Cozumel is another Category 5 property, which requires just 35,000 points per night on standard dates. Or, you can redeem IHG Rewards points for a more luxurious stay at the InterContinental Presidente Cozumel Resort and Spa.

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

Costa Rica

Even though Southwest Airlines is best-known for domestic travel, the airline can take you as far as Costa Rica. Here, you can experience a different culture, but not too far away from home — and without jet lag.

Southwest services two different airports in the country: Liberia (LIR) and San Jose (SJO). This gives you easy access to the beaches, rainforests and volcanos in both northern and central Costa Rica. Since Southwest prices their flights as one-ways, you can even fly into one airport and out of the other without having to do a complicated search.

Related: 6 adventurous activities in Costa Rica for families

Stroll on the beach in Puntarenas, Costa Rica. (Photo by Matteo Colombo/Getty Images)

With many points-friendly hotels, Costa Rica is also very easy to vacation in if you are on a tight budget. One of our favorite properties is the Andaz Costa Rica Resort at Peninsula Papagayo, where you only have to redeem 20,000 World of Hyatt points per night for a stay. The property is also only a 30-minute drive from Liberia Airport.

Likewise, there's no shortage of Marriott properties throughout the country. Whether you are looking for an inexpensive property in San Jose or a beach resort, there's something for everyone — including the all-inclusive Planet Hollywood Costa Rica thanks to Marriott's recent expansion into that market.

Fly into:

  • Liberia (LIR) with nonstop flights from Baltimore (BWI), Houston (HOU), Denver (DEN) and Ft. Lauderdale (FLL).
  • San Jose (SJO) with nonstop flights from Baltimore (BWI) and Houston (HOU).

Bottom line

Southwest can take you to a ton of unique destinations in the U.S. and abroad. Best of all, you can always fly buy one, get one, as long as you are a Southwest Companion Pass holder. I'm in my 13th year as a pass holder and it's allowed my family to visit much of the U.S., Mexico and the Caribbean at a significant discount.

Consider applying for a Southwest credit card to get a head start on your Companion Pass journey to head to these or other Southwest destinations.

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