Our First Trip as a Family of Four: Mistakes Made and Lessons Learned

I follow a few travel blogs (TPG, OMAAT) that have adequately warned and prepared me for what to expect when traveling with kids. But, “we don’t rise to the level of our expectations, we fall to the level of our training”. And since there is no such thing as family travel camp (there’s an idea), our training has been non-existent.

Below I’ll discuss what I think we did right on our first experience traveling as a family of four, highlight some areas for improvement, and just poke fun along the way. I’ll go in chronological order to give a better idea into why we made some of the decisions that we did.

The Plan: Fly to Orlando, then San Antonio, drive to Austin, and then back home

We made plans to go to Orlando, FL to spend New Year’s eve with family. We were to rent a huge house that sleeps 18 people so everybody would be comfortable. However, the rental was scheduled for Sunday through Thursday. I already made plans to take the entire week off from work. So obviously there is a window of opportunity to fit in some additional travel. We ended up booking flights to San Antonio, TX with the intent of sight seeing upon landing, and then heading to Austin where we would spend the rest of our weekend.

We did a ton of research prior to taking off. First, our little guy is just 3 months old at the time and we wanted to make sure he would be comfortable. Second, it would be our first time traveling with two kids in tow. And last, neither of us had ever been to San Antonio or Austin. So my wife and I read up and shared a few links with each other in preparing for this trip.

Our First Mistake: Parking at the airport

At $8/day, we decided that parking at the airport’s long-term parking lot was our best option. I didn’t think that grabbing a Lyft/Uber would be a good option since we would need car seats and we have a few items of luggage. This would of been the first time I’ve ever parked at a parking lot associated with the airport. We normally use Groupon to park at a nearby lot. When we got there, the long-term lot was “full” and we were forced to go to the daily garage where they charge $12/day. I expected to pay $64 for parking and we ended up paying $108 for our stay. I wasn’t happy!

The thing that got me to park at the airport was the promise that we would be charged per day, not per 24hrs. And that the rate was all inclusive and we would not be charged additional taxes and fees. Nothing is more annoying to me than being told my bill would be X and then it turns out to be Y. I called after the fact to confirm this and it turns out the information on BWI’s website is completely wrong.

Our First Win: Packing super light

We flew with Southwest and we technically could’ve checked 6 full bags. But who’s carrying all that across the airport? We managed to fit all of our stuff into just two luggage bags (one full size, one medium), including bulky items like arm floaties for the pool, diapers, wipes, etc. We also had backpacks for the stuff we needed on the plane. We considered the fact that we would have access to laundry on the first leg of the trip in Orlando. So we packed clothes for 4-5 days even though we would be gone for 8.

We only brought one car seat and stroller, which we checked up front rather than taking it up to the gate to make things a little easier. We like to use a cover for our car seat to protect it from the elements. Checking it at the gate would mean I would have to keep that oversized cover on my back for longer than I would of liked.

Mistake #2: Not having a proper car seat

We tried using a travel car seat for our toddler so we wouldn’t be carrying two car seats. The travel car seat was easy to transport, but it wasn’t right for our circumstances. Our baby was uncomfortable and frankly, I don’t think the seat was adding much in terms of safety. Thankfully, we didn’t do any driving in Orlando except for the trips from and to the the airport.

Related side-note: Upon landing in MCO, we made our way the car rental wing where we had prepaid for an economy car with Advantage. When we got there, the agent informed me that there were no economy cars and that I would have to pay to upgrade to a full-size model. After a long day of traveling, I relented with the intent to fight this later. This turned out to be a grave mistake. I tried calling after the rental was completed and every agent basically told me that now that since the rental period was closed, there was nothing that could be done. I won’t ever rent a car from Advantage again.

A Win In My Book: Avoiding all theme parks in Orlando

Our kids are way too young to appreciate anything at a theme park. They still take naps in the middle of the day and my toddler gets super cranky if she misses it. I was worried that we’d spend a couple hundred dollars for no apparent reason. I wouldn’t fight with my wife if she decided to take our oldest. But I was not looking forward to it. I was delighted when the 3rd and 4th day came around and there was no mention of going to the parks. When did theme parks get to be so expensive anyway?

A Chance at Redemption: We rented a car seat in Texas

We knew we’d be doing a lot of driving in Texas, so we bit the bullet and rented a car seat with our rental. It was completely worth the ~$30 we paid for our 3-day rental. It allowed my baby to nap properly during longer rides, which in turn allowed us to maximize our time. For example, we drove from San Antonio to Austin which took a little over an hour. Both kids took quality naps in their car seats. That allowed us to keep the party going in Austin.

Residence Inn For The Win: Paying attention to hotel brands

Prior to having kids, a hotel was just a place to lay your head at the end of the day. As long as it was clean and safe, the accommodations did not matter much to me. Location and price were the only important factors. Now that kids are in the picture, I find that I am paying more attention to the hotel brands and familiarizing myself with their individual signatures.

I chose a Residence Inn property in Austin primarily because there is typically a living space that is separate from where the beds where located. My thought was that when the kids go to sleep early for the night, my wife and I can hang back for a while. I still have not accepted that our bedtime is slowly becoming the kids’ bedtime. We really enjoyed this hotel. Other reasons for choosing this property: it allowed us to use our free night certificates, it was super close to the city center, and parking was free. Actually, free parking was the first filter I used. I didn’t want to pay $40/day to have a car. And a bonus that I did not expect to use, free breakfast. Breakfast tacos are so popular in Austin, that I expected to get out and try new things everyday. I forgot how picky kids were. Free breakfast suited us just fine before getting our day going.

Bottom Line

All in, we spent a little over $1,200 on this trip. Thankfully we had free night certificates and points to use for our hotel stay. And you know we used our Southwest Companion Pass again. My wife and I feel that we crushed our first trip as a family of four. We were tired at the end of the trip, no doubt. And we made plenty of mistakes that we will be correcting on the next round. But overall, we feel like the experiences and memories we created for the babies were worth enduring the struggles. On to the next one!

Please hit up the comments with any suggestions, hacks, etc for traveling as a family. Im always looking to optimize.

4 thoughts on “Our First Trip as a Family of Four: Mistakes Made and Lessons Learned”

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