Tuscany Cortona, Italy

Jamey never wanted to go to Europe. Melissa always did, so we went, and Tuscany is the place that turned him. The slow pace, the late dinners, the piazzas, the espresso and the limoncello after, the old buildings, the best food we’ve had anywhere. It’s country. Magical country with charming people and nothing to check off. It’s probably our favorite place on earth, and this is the trip where we figured out how to do it: one base, nine nights, day trips fanning out.

Home was Agriturismo I Pagliai, a working farm up a gravel road in Montalla, about eight minutes from Cortona’s walls. Honest review: the house itself was just okay. A lot of Tuscan farm stays are decorated like somebody’s grandmother’s place, and this was one of them. But the location carried everything: Vittorio and Francesca, a killer farm dinner one night, and a pool with the whole valley dropping away beneath it. That pool did more work than any sight on the trip. The girls swam it out every afternoon, and nobody melted down over one more medieval church.

The day we’d tell you to copy

Morning in Cortona: wander, shop, lunch. Back to the farm when it gets hot for the pool, the nap, the quiet. Then into town again for a slow dinner on the terrace at La Loggetta, overlooking the piazza. Wine, limoncello, no hurry. That dinner is maybe one of our favorite meals ever; reserve a spot on the balcony. Most summer nights there’s live music in the piazza below, and our nightly ritual was Uno and gelato on the steps under the clock tower. We ran that exact day a couple of times and it never got old.

The two farm days were the other keepers. Podere Il Casale near Pienza is an organic cheese farm where you make pizza in their oven and eat it at a long table with their own pecorino. And the truffle hunt at Villa Magna Tartufi outside Arezzo: you follow the dogs into the woods, they find one faster than you’d believe, and lunch is built around what just came out of the dirt.

43.2748° N, 11.9854° E

The hill towns worth the drive

Two earned their place. Montepulciano for the wine cellars carved under the town (De’ Ricci runs down beneath a church) and a long lunch. And Pienza, tiny and perfect, best in the evening after the day-trip buses clear out. For a sunset night out, Palazzo Vecchio winery near Montepulciano runs “Sunset Vineyard Nights”: wine, dinner, and music out on the rolling hills. The one we’d skip is San Gimignano. It’s the famous one, and it’s so crowded and touristy that the charm you drove for is gone by the parking lot.

One real headache to plan around: the ZTL. Cortona, Montepulciano, and most of these towns wall off their historic cores to traffic all summer, cameras enforce it, and a rental car is not exempt; fines run €83 to €332. Park in the lots outside the walls and walk in. In Cortona, Parcheggio del Mercato is free and about a seven-minute walk to the center.

Where we ate

Cortona feeds you well enough that we booked dinner most nights and never regretted it. La Loggetta is the one we’d send you to first (the terrace, above). La Bucaccia is the proper trattoria with an owner who runs the room like it’s his living room, which it more or less is. Sartù is dinner in a small stone cave and worth it for the setting alone. And gelato in Piazza della Repubblica is a nightly tax you pay happily.

The honest caveat

You can reach a lot from Cortona: Perugia and its Baci chocolate factory, Assisi, the little “bird-cage” funicular up Gubbio, Lake Trasimeno twenty minutes away. The temptation is to reach for all of it. Don’t. The day we strung three Umbrian towns together was the one day that felt like a job. Two stops a day is the whole trip. The rhythm is the magic here: explore in the morning, swim and nap in the heat, eat late. Protect it.