We were already bored. Carter and I had the next few days off together, but we had no real plans.

I opened my laptop and started to look for local activities for the afternoon and evening. We needed something fun and different, but I didn’t want to waste a ton of time or money arranging it or getting there.

At some point during my search, I remembered a large stash of Chase Ultimate Rewards travel points that had been adding up in our account over the last several months.

The idea of spontaneously packing a bag, hopping on an airplane, and going to a different city has always been appealing but out of reach for me. However, one of the things I’ve realized over the past few years is that building memories doesn’t necessarily have to cost a lot.

Between noon and 1 pm, and with the help of the internet and some travel rewards points, I managed to book direct flights later that day to Nashville and a stay at a pretty cool hotel for a grand total of $22.40. We were there six hours later, getting off of the plane in a different timezone.

Booking Free Flights

Southwest has a few direct flights per day between Charleston and Nashville, and it’s a quick one that gets you there in a little over an hour. They are conveniently one of Chase’s travel partners, and I used 19,968 Southwest miles to book one round trip flight to Nashville, TN.

Carter flew for free with my Companion Pass. A 5-minute call to Southwest was all it took to change my designated companion from my wife to my son for the flight. You can change your companion up to three times per calendar year.

The $11.20 taxes and fees for the flight are unavoidable. Between the two of us, our round-trip flights cost $22.40.

Southwest Companion Pass

The Southwest Companion Pass is huge if you live near an airport that Southwest flies out of. It allows any friend or family member I choose to fly with me for free every time I book a ticket, even if my ticket is booked with frequent flyer miles. It can be earned by accumulating 125,000 Southwest miles within the same calendar year, which is easier and cheaper than you may realize.

With a few months’ worth of regular spending strategically placed on two Chase Southwest credit cards, you can easily get a companion pass that lasts for almost 2 years. Since receiving it last year, we’ve also used our companion pass for free flights to New York, Las Vegas, and Costa Rica.

Apply at the Right Time

The key to making this strategy work is getting the timing right. Southwest miles have to all be “earned” within the same calendar year to qualify towards the pass.

I accomplished this at the end of 2018 by applying and being approved for Chase’s Southwest Business card (60,000-mile bonus) and their personal Rapid Rewards card (40,000-mile bonus). The bonus miles are awarded after minimum spends on the cards within three months of approval – $2,000 on the business card and $1,000 on the personal card at that time. Chase’s definition of a “business” is also a pretty loose one.

I opened the cards in October and November 2018 but waited until after January 1st to complete the $1K and $2K minimum spend requirements. By doing this, both bonuses totaling 100,000 miles were awarded in January 2019. All I had to do after that was spend $10,000 more on either card, and the pass was automatically issued and valid through December 31, 2020.

Although the CP requirement has recently changed from 110,000 to 125,000 miles, current bonuses for each card have increased as well. You can easily get a Southwest Companion Pass within a few months.

The Airport

With no luggage to check for just an overnight trip, we headed directly for security after parking.

TSA Precheck

The line was fairly long, but TSA Precheck is a benefit included with the Chase Sapphire Reserve credit card. We were through the expedited security line in less than 5 minutes without taking off shoes or removing our computers from my one carry-on bag, skipping the regular line.

Priority Pass Lounge

Another benefit that the Chase Sapphire Reserve card includes is Priority Pass Airport Lounge access. These lounges are super comfortable places to wait in the airport rather than the crowded seating at the gate. Food and drinks are all complimentary. Many have places to lie down, stretch out, and take a quick nap or to get some work done for business travelers.


After landing at the airport in Nashville, we grabbed a 15-minute Uber ride to the Thompson hotel.

Because we just stayed overnight, it wasn’t practical to rent a car. We probably could have saved a little money, but the time it would have taken just wasn’t worth it. Uber rides over the two-day trip cost a total of $103.65.

The Hotel

I booked a suite at The Thompson Hotel with 30,000 Hyatt points that we still had from a spring trip we had to cancel due to COVID-19. You can almost always score Hyatt stays for far fewer points than this, but I wanted to surprise Carter with a really nice room, so I was willing to fork over some extra points. As an eight-year-old, hotels are one of his favorite parts when we travel.

It usually pays off to send a genuinely nice e-mail directly to the hotel manager, which I had done a few hours before while waiting for our flight to leave Charleston. Nothing elaborate, just a note explaining the purpose of the trip and asking for any recommendations.

At check-in, they upgraded us to an executive suite without asking and for no extra charge.


Among other things, Nashville is known for its barbecue. Our visit to the Peg Leg Porker lived up to the hype. It’s a hole-in-the-wall BBQ joint that our Uber driver recommended a few blocks away from our hotel.

Ice cream on Broadway for dessert.

Breakfast the next morning was at a place called Biscuit Love. Also recommended by our driver the night before, it didn’t disappoint.

We spent a total of $104.12 on food over the two-day trip.

The Music

Without a doubt, the highlight of our trip was watching Carter fall in love with country music.

Broadway is lined with open-air honky-tonk bars. In a few short blocks, you can hear dozens of musicians playing live music.

I had planned on taking him to a children’s museum early in the day. I couldn’t have been prouder when he told me, “Dad, I just want to go into all of these places and sit and listen to music.

We spent about an hour or so in the Johnny Cash museum which he absolutely loved. Admission for both of us was $42.41.

Cowboy Hats

The only thing we bought on our trip, besides food, was a cowboy hat for Carter that cost $49.26. He wore it for the entire next week.

Dave Ramsey

When Carter found out that Ramsey Solutions headquarters is located just outside of Nashville, there was no way we were going home without a trip to see it. After all, Dave really inspired the start of our journey toward financial independence.

Although Dave was out of town that week, after a (very expensive) 30 minute Uber ride, we were able to meet Chris Hogan and Ken Coleman and watch some of their live broadcast before heading to the airport for our flight home.

Back to Reality

A few hours later, we pulled back into our driveway. He ran inside and told his mom all about our one-day adventure.

Only a little more than a day after searching for something to do for a few hours, Carter and I had an experience that neither of us will forget. It cost a grand total of $321.84 – less than you’d make in a regular 12-hour shift at the hospital.

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