Where Do You Fly Into To Go To Siesta Key

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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a large passenger jet sitting on top of a runway: (Photo by David McNew/Getty Images) © The Points Guy (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.

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

a building with a mountain in the background: (Photo by DOUGBERRY/Getty Images) © The Points Guy (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

a group of people standing on top of a snow covered mountain: Steamboat Springs. (Photo by Zach Shortway/Getty Images) © The Points Guy 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 tree in front of a building: A Southern manor located in the downtown historic district of Savannah, Georgia, stands proudly among the old oak trees. (Photo by Getty Images) © The Points Guy 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.


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