Our destinations depend on all sorts of things: family recommendations, general curiosity, intriguing work opportunities, the state of our budget, the time of year. We started our adventures in Saskatoon, Canada simply because when we (rather belatedly) punched our criteria into Airbnb, the algorithm told us it was either Saskatoon or Omaha. As Kansas City natives, Omaha sounded like a rather anticlimactic way to kick off our adventures, so we made the two-day trek up to Canada. We visited Goldendale, Washington because it looked like a good distance between Seattle and Boise on the map. We went to Albuquerque because my grandmother has fantastic stories from her time there. And we navigated a series of local buses to get to the Kentish countryside in England because someone had turned their old windmill into an Airbnb, and that just sounded awesome. (It was.) We tend to follow warmer weather in the winter and cooler weather in the summer. We stick mostly to the US and Canada because we travel with our dog Odin. And we are quietly ticking off the states we’ve been too, so eventually we’ll wind up in Alaska for the sake of finality. In general, our advice here is pretty simple. Pick out a place that you’ve always wanted to experience. With that initial destination in mind, sketch out a few additional legs to the journey and see where it takes you.

We tend to make our plans between six and twelve weeks out. The longer you want to stay in a single Airbnb, the further in advance you should make your reservations. Month-long stays should be booked two to three months in advance. Otherwise, your search will be littered with perfect listings that have just one weekend booked by someone else smack dab in the middle of your potential stay. Week-long stays are much easier to book a month or so out. Keep in mind that different locations fill up at different speeds, and that the time of year or local events can have a major impact on Airbnb availability. For example, summers at this beautiful cottage in Cape Cod fill up ridiculously far in advance. When it comes to making your travel plans, the best rule of thumb is this: start sooner rather than later. We have successfully made same-day reservations, but in general the longer you wait, the harder it gets. Those words of wisdom are rooted in an embarrassing amount of first-hand experience due to some overly optimistic, procrastinator-prone defaults in yours truly. (Side note: We’re rather rigid planners because our criteria is uncommonly strict: we’re looking for dog-friendly, remote-work-ready, entire place Airbnbs. The more flexible your criteria, the more your planning timeline will loosen up.)

We’re big fans of one month stays. When we first started traveling, we moved every week and we quickly discovered that that pace was just too darn fast. Every weekend was gobbled up by travel, we rarely had the opportunity to establish any significant connection to place or people, and after eight weeks of this unsustainable clip, we were ready to throw in the towel. When we transitioned to predominantly month-long stays, the whole tenor of our travels changed for the better. First, there are some incredible month-long discounts that kick in once you pass the 28 day marker. We’ve enjoyed discounts upwards of 40%, which brings places that would otherwise be completely unaffordable into our price range. Second, a month means that an Airbnb really starts to feel like home. By the time we leave, we’ve fully settled into the rhythm of the neighborhood, found our favorite coffee shops and bars, established our morning walking routine with Odin, sometimes even joined a local gym or yoga studio. Third, we’ve usually got that travel itch again by the time the month is up, which means we’re actually excited when travel day rolls around. And finally, and of equal importance, it’s just a month. There have absolutely been certain Airbnbs and locations we’ve wished weren’t month-long commitments. But when it gets right down to it, a month in a new place goes by pretty quickly. In our mind, the benefits of a month-long stay are well worth the potential downsides of navigating a disappointing Airbnb.

We drive! In a tiny, two-door hatchback no less, traveling coast to coast and back again. There are a couple of benefits to traveling with a tiny car. One, it’s limited size restricts overpacking. With Odin in the backseat, we have to fit our belongings in just the little storage area in the back. And two, it’s easier to parallel park in crowded cities. (Although to be completely honest, Jay has a much better handle on that skill than I do, regardless of the size of the car. Parallel parking isn’t exactly a skill I refined as a Kansas driver.) And while this car is reliable, it’s over a decade old. We’d be hard pressed to recommend taking a more valuable car on extensive road trips. The wear and tear can be considerable. More broadly speaking, we’ve loved the perspective that driving from location to location has given us. There’s a reason road trips have such a solid footing in Americana cliques: the landscapes across this country are as varied as they are impressive. In the same way that exploring a city by foot provides a more intimate perspective than exploring by car, driving has made our destinations feel more known than arriving by plane would have allowed. They’re contextualized by their surroundings. If your own American travels involve driving, keep an eye out for Scenic Byways. This tip from Jay’s grandfather has paid off time and time again.