I just got back from a weeklong trip with my fiancee. It was one of the first times I was able to get out on my own with her, do whatever planning we wanted to do, and see it come to fruition. I’ve got to say, going with the wind on some of those days and just seeing where we ended up was exhilarating. I’d say the only downside to it all is that “real life” now feels pretty bland and structured, now. It’s no fun having to do what you must instead of whimsically going with your gut any given moment.

This sort of living excited me for our future, though. We definitely plan to make more trips across the US and sort of just wing it. Of course, even when you’re winging it you have to be prepared in some sort of capacity. That, we came to learn, mostly manifests itself in the form of what you brought along with you while traveling.

Here’s the thing. We could’ve used more shipping supplies, such as cardboard boxes and packing tape, while we were out on the road. The amount of trips I made into and out of someone’s AirBNB just to unpack and pack the vehicle was more than I’d like in the future. So, though shipping supplies seem kind of like an odd option to include for the next few trips, it’ll make a ton of sense when we can load and unload our vehicles so much easier.

I think what makes a good trip (especially on true vacation) is not much of a plan at all.

That may sound contradictory, but I really mean to say that too much of an itinerary can stress people out, especially if people are late or at the wrong place or in a hurry. Rather than building out this elaborate plan of things to do for each day, why not kinda see where things go from one day to the next?

My fiancee and I managed this perfectly. We knew which places we were visiting on certain days (in terms of the actual cities). And we had an idea of what it is we wanted to do, such as see certain breweries or beaches. But in terms of when we did it and exactly what time? Well, that was left to the wayside. We had much more fun just kinda showing up when we wanted to, having fun for as long as we wanted to, and leaving when we wanted to.

I know this is an entirely different model of vacationing that most people aren’t accustomed to, but we were entirely stress free the entire time. And did we argue or fight at all? Not once.