How we’re choosing our cities

We’ve spent a lot of time researching which cities to visit on our grand adventure.

The number one criteria is walkability. In Houston, we’ve been spoiled by living across the street from a grocery store for the past couple of years, and that’s definitely something we would like to retain. We want to live where the action is: a neighborhood with residences, restaurants, entertainment, shopping – where you don’t need a car. In some cities, like Montreal, there are lots of neighborhoods to choose from. In others, there’s really only one or two areas that fit the bill.

Affordability and availability of furnished apartments is a close number two. Some places we looked at – Boston, for example – have plenty of options on Airbnb or Homeaway, but at a price point that’s above our budget. In other places, there are just not many short-term furnished rentals on the market. So we’re avoiding the biggest cities that might seem obvious choices, and the places that are too small to support the tourism infrastructure we need. Wilmington is a perfect example of this category – with the added benefit that it’s a short train ride away from Baltimore, Washington, D.C., New York City, and Philadelphia.

Next is weather. Braden grew up in Chicago, but I’m originally from Phoenix and very much a weakling when it comes to cold weather! Neither of us has much experience driving in snow and ice, so we wanted to make sure we find somewhere temperate to spend the winter. So right now we’re considering Asheville, Savannah, and Nashville for December through February. On the flip side, I’m SO excited to trade Houston’s hot and steamy summer for Montreal’s average July high temperature of 78°!

Finally, a lot of people have been surprised that our adventure is so east-coast centric. I guess the west coast fills in that untethered Millennial concept a bit more? But it’s a pragmatic choice: cities are just a lot closer together back east – so there’s a lot more to choose from. Say Pittsburgh is just not working for us. We can pack up and be in Columbus or Cleveland in less than three hours. If that happens in Salt Lake City? The next big city is Boise at almost five hours away. So we’re saving the West Coast for later on in the journey.

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