Easing into Travel

the introduction

August 20, 2025 · 2 mins read

One introductory travel strategy we used was to ease into travel, to help with confidence for both ourselves and our kids. Our goals were:

  1. Learn some travel tricks specific to airplane travel with toddlers.
  2. Get extra practice with sleeping in a new place.
  3. Get a sense of the most important things to pack.

Certainly, it’s not always possible to do this for logistical reasons, cost, or time, but if you have the flexibility, this “warm up” plan worked really well for us. In order to do this, we chose a couple simple destinations, for 1-3 nights each.

Our first trip was a plane ride to a place we had lived before (any destination you’re pretty familiar with could work well here). This way, when we rented a car and car seats for the first time, we wouldn’t have a ton of stress about navigating a new place. I was also looking for a relatively short (<2 hour) plane ride where we could take a direct flight. Not a necessity at all, but again, we were looking to ease in. Our first trip was just a couple nights, where we rented an AirBNB. That gave us the flexibility to have separate bedrooms for our kids. When in doubt, change fewer variables at once (when you have the chance, of course!).

Other early trips included:

  • Road trip 6 hours away when our first born was 11 months old. We had 2 nights and wish we had more time, given the length of the drive and the number of stops along the way. It felt like the drive was too long for the short stay at this age.
  • Road trip 6 hours away when our daughters were 3 months and 2 years. We stayed a week and went with extended family, so this was much more manageable.
  • Road trips to my in-laws house (from the time each girl was a couple weeks old), mostly long weekends (less than 3 hours). Drive length makes a weekend here pretty easy.

Taking frequent small trips has made it easier for our kids to sleep in a new place in particular. Getting used to car rides, rental car seats, and airplanes are all great advantages too!