Do check out the essential items for a digital nomad’s backpack that Philip shared. There’s quite a few non-digital ideas in there too!
I don’t have a brand of shoes that I can recommend to you, but my advice is get them comfy and get some that you really like from a stylistical perspective. You will most likely be wearing them until they die.
Even though you haven’t asked for recommendations for places, I’ll throw a couple of them in there: while western Europe is the more popular destination, I would really recommend having a look at the more eastern countries. Slovenia was a joy to go through, and I particularly liked Ljubljana, and Poland was pretty awesome too. Go to Katowice or Krakow for a week or two, and then take the a sleeping wagon north to Gdansk. For me at least they easily outshine the more popular western cities. It is a highly subjective point of view though
Also, my advice is to not make too many, too time specific plans. This might be specific to us, but the best part about a big adventure for us is to be able to decide where next to go, a couple of days before we go there. It can become quite a drag to have to go somewhere else, when you’ve just discovered this awesome new little city that no one’s ever heard about.
And don’t underestimate the distances. Unless you’re going with the airplane they are a lot bigger than they look on the map!
Oh! And a SIM card! You should be able to get one from any country in the European Union, and then Internet access will cost you the same anywhere else. They’re pretty cheap here in Poland, but getting through the polish interfaces can be a bit daunting
And Gretchen, I hope you’ll have an awesome adventure!
Give me a ping me if you get to Romania. No promises (me and my husband are nomading quite a bit at the moment too), but I’m inspired by your story, and would love to hear the rest of it.