Out of Office, Somewhere

Every taxi driver asks Tom where he’s from. When he says the U.S., they inevitably tell him he speaks Italian perfectly, with a flawless accent. Tom smiles, because he knows I’m laughing at the fact that it’s happened once again—“sei troppo gentile.” Meanwhile, I’m still figuring out how to ask for the bathroom without accidentally ordering a goat.

We are Tom and Michelle, which sounds tidy until you get into the details. Tom is a semi-retired antitrust attorney who grew up in Milan with a diplomatic father, which explains the Italian. Michelle, on the other hand, has tried. Private tutors, community college classes, years of “practice”… and yet the pinnacle of her Italian is: “un cappuccino per me, per favore.”

Michelle is also an entrepreneur who still runs a small open-box furniture resale company, GoodbyHello.com, with her best friend from grade school—because some people never outgrow group projects; they just add invoices.

This is the second marriage for both of us. We’ve combined four kids, acquired two small, adorable, funny grandchildren, and somehow decided the next sensible step was to leave our dogs behind and wander Italy for two months. We miss those dogs more than is reasonable. We talk about them like they’re deployed, and we suspect they are plotting revenge via Instagram.

We started our Italian adventure in Momeliano, near Piacenza, with a quick visit to Nancy, Tom’s sister, and her adorable Lagotto, Mia, who immediately claimed us as her people. From there, we spent a day in Milano, marveling at ice block displays on the sidewalks in anticipation of the Olympics—apparently, Italians celebrate global athletic events in the most literal way possible, and fabulous old trams – some come with a complete dining adventure. Another day we wandered around Piacenza, including a visit to the art museum to see a Klimt painting that had been stolen, found in someone’s backyard, and then, sadly, on loan in Korea. Art heists: Italian edition.

After our northern adventures, we drove to Siena, our home away from home for a month. We were looking forward to bike rides throughout Tuscany, hitting the strade bianche, and feeling like vintage Italian athletes… only to be thwarted by relentless rain.

Siena, which is breathtaking, medieval, and—during our stay—approximately 94% rain. Siena in the rain is still Siena: stunning, small, dark, and very uphill. After a while, even beauty starts to feel like it’s judging you. We escaped to Florence for a few days, then Lucca, chasing sunshine like amateurs who forgot to check a weather map. Italy, it turns out, was not interested in our plan. Most of the country was under the same gray sky, politely soaking us everywhere we went.

So we’re leaving Siena early and heading back to Florence, where we once had an apartment and foolishly sold it last year. It will feel like coming home—which is ironic, considering we are technically homeless tourists with excellent opinions. We laugh at the fact that we’re complaining about being “stuck” in Siena—one of the most beautiful cities on earth—because we are not unaware of how lucky we are. This blog lives right there: between gratitude and grumbling, wonder and wet shoes, love for travel, and a strong desire for dry socks.

We’re out of office. Somewhere. And we’re living our best life!