In the next few posts, I’ll be writing about our family trip to Italy and Switzerland in June and July of 2018. On the trip: Myself, Jess (my wife), and Evie (our ten year-old daughter). Italy hadn’t been a dream destination for any of us, but sometimes the road calls you in unexpected ways.

Jess’s cousin Sara has been working in Milan for the past couple years, and has offered her couch (ok, really, her spacious spare bedroom) to family members who wanted to use Milan as a launching point for exploring Europe. We kept saying “maybe we should” and realized if we didn’t start really planning it, it would never happen. Life has a way of slipping by while you’re planning for the future.

So we stared seriously discussing it in February of 2017. We weren’t sure what countries we wanted to visit, how long we wanted to go, and whether we would bring our daughter with us. But if there’s one thing I love to do, it’s obsessively plan things, and this was a meaty problem I could sink my teeth into.

The trip started to really firm up in November of 2017, at another family member’s wedding. Over a few drinks we talked details, prices, potential timelines, and more. We decided for sure we were bringing our daughter, too. Over the next few months we dialed it in, buying airline tickets in January and then solidifying our destinations and how we’d get between them. Many people have asked if we followed a recommended tour, or booked ourselves onto one. We did not — we dealt with all the details ourselves, with all the pros and cons that implies.

I know this post has no grand descriptions or photos, but I wanted to set some context for the upcoming posts. This was a life event, not a “vacation.” It was an adventure. It was a trip we knew would cost us more than we could really afford. We planned accordingly, squeezing as much out of it as we could. It took us 16 months to nail down everything. I bought four travel books. I spent hours on youtube and travel blogs, watching people teaching Italian phrases and trying my best to understand the ins-and-outs of the European rail system and the cultural norms of the Italian cities we were visiting. I hunkered down with travel booking and review websites. We had to renew passports, pick out hotels, buy train tickets, fine-tune timelines, everything. It was a completely different trip than anything we had done before, in many ways, and it was hard not to over-plan and burn out.

In the end, our trip had us arriving in Milan on June 23 and departing on July 7. In-between, we would visit Turin, Rome, Orvieto, Florence, Pisa, Wengen (Switzerland), and Venice. We would spend five nights in Milan (thank you cousin Sara!), and two nights many other places.

So. Settle in, grab an espresso or limoncello (or even, to borrow a phrase, “a nice Chianti”), and check out where these eager feet got off to this summer…