Where should I go with my free airline points?

southwest plane los angeles

At the moment, I have so many options for free travel I can’t make a decision. Take another trip to NYC? Maybe a Pacific Northwest vacation to Seattle and Portland? Or maybe somewhere more exotic like Puerto Rico, Aruba, Jamaica, or Costa Rica? So many possibilities!

The reason I have these options for free travel is not because of any insider travel blogger freebies, but rather because last year, I applied for and opened a Southwest credit card. That was the greatest travel decision I ever made.

The 50,000 bonus points I received from signing up, combined with the 10k points I had already accrued and the 2k or so points I continue to amass each month by paying all my bills with the card (score!), means that I now have at least three free trips coming up. (I HIGHLY recommend getting an airline credit card if you don’t already have one.)

The problem now is deciding how best to redeem these points to maximize their value.

Options: NYC vs Puerto Rico?

Initially, I wanted to use points to travel to New York. I haven’t been to NYC in a few years, and as I mentioned in my list of places I want to visit in 2015, I especially want to spend time in Brooklyn.

times square nyc

While comparing prices, though, I noticed something odd: For roughly the same amount of points I’d need to fly to New York, I can fly to San Juan, Puerto Rico instead. Puerto Rico!

Since my travel has been focused exclusively on the U.S., Canada, and Mexico thus far, I’m always looking to branch out. Puerto Rico is in the Caribbean so it’s not like I’m going to the other side of the globe, but at least I’ll finally be moving beyond continental North America.

So Puerto Rico it is! I’m hoping to visit later this year. Probably September, when hurricane season kicks in (living dangerously!) and prices are lower.

Other possibilities: Glacier National Park?

The top domestic destination on my wishlist right now is Glacier National Park and its famous Going-to-the-Sun Road in Montana, but the closest Southwest flies to there is Spokane, Washington. Flights to Spokane aren’t particularly affordable, and from there I’d have to rent a car and drive five hours to the park. That would be very time-consuming and expensive, so I’ve decided that a Glacier trip would not be an ideal use of points.

All about Cleatus, the lone American crocodile who lived at Dry Tortugas for 14 years

As for other options, Las Vegas and all the Utah national parks are high on my list. In Utah I can visit Zion, Arches, and Canyonlands National Parks. In Vegas, there are the casinos, of course, plus all the shows on the strip and attractions like the Stratosphere rides.

But there’s a good chance I’ll be moving to the west coast soon, so I think the smart thing to do is hold off on any trips to that half of the country until then.

welcome to vegas sign

So what does that leave? Aside from Puerto Rico, I’m looking at south Florida again (another Miami vacation would be sweet), and possibly somewhere in the Northeast, like Boston or Hartford. I’d love to do a New England road trip for 10 days through Maine, New Hampshire, Vermont, Connecticut, Massachusetts, and Rhode Island, since those destinations are often overlooked by travel bloggers. That’s also the area of the country where I’ve spent the least amount of time.

I love maximizing my travel opportunities, so even though I have these free points available, I’m still going to wait for sales so I can use as few points as possible for each journey. That way I can potentially stretch the points into four or five trips.

Conclusion: Still undecided but leaning towards…

As of now, I’m planning to save my points for Puerto Rico, Pittsburgh (for a family visit), and Los Angeles, where I hope to move next year. But that’s all subject to change depending on upcoming sales and discounts, or changes in my own perspective.

I strongly advise the frequent traveler or wannabe frequent traveler to get an airline credit card. It doesn’t have to be Southwest – I’m not being paid to endorse them or anything. I prefer Southwest because they’re affordable and they still allow free checked baggage, unlike many other carriers, but there are some drawbacks with Southwest – they don’t travel to Canada, for instance.

plane airport

So do your homework, decide where you’d really like to travel, compare the various airline credit cards, and get yourself one. (Pay off your full balance at the end of each month, of course, to avoid crazy finance charges.) Then you too can deal with the awesome problem of trying to figure out where to take your free trips!


  1. We were very pleasantly surprised by our trip to Puerto Rico! We loved it there! There are beautiful forests (El Yunque National Forest, and more!), incredible beaches, and wonderful people. And for something quirky, check out the Arecibo Observatory!

  2. Couldn’t agree more about the airline points credit card. We have a VISA card through United Airlines. We also have an AMEX card through Hilton Hotels and that card we use a lot and we’ve scored many free (and/or discounted points) nights and we always ask for an upgrade which has landed us in many suites – sweet!

  3. We loved Puerto Rico! We went to Vieques Island where the beaches are still undeveloped. We usually had the beach to ourselves and saw wild horses wherever we went. Plus, the Bio Bay. It’s one destination that we want to return to for sure.

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