Home Base: Villa Conti, Terentola
We based the whole Tuscany stretch at Villa Conti, a private home in Terentola near Cortona that was first built in 1786. Pool, olive trees, a small kitchen and old-style bathrooms — super cute, a little creaky, and exactly the way to experience this part of Italy. After an all-night travel day we arrived on a Saturday, had a light dinner, and called it an early night.
A Cooking School Morning at La Braccesca
Day one we spent at La Braccesca winery, starting with a short cooking school where we learned to make bruschetta and pici, the “poorman’s” pasta of Tuscany. Then a tour of the winery and cellar, followed by a great lunch. The rest of the day was villa time and the pool. Not a bad way to shake off jet lag.
San Gimignano and Monteriggioni
Day two took us to two hill towns, each about an hour from the villa. In San Gimignano we started with Italian coffee with a view (Mokaflor, just outside the wall), then wandered streets so old and picturesque it hardly felt real. From there, Monteriggioni, which looks like a fortress from the outside. Lunch was at L’Antico Travagtio Osteria: ribollita, the traditional Tuscan soup, homemade pappardelle with wild boar ragù, and a bottle of Chianti Classico. Wine is wonderfully inexpensive here. We finished with gelato, and in one small shop they stitched McKenzie’s name into a piece of paper as a keepsake.
Montepulciano: Two Wineries and a Chef at the Villa
Day three was winery day near Montepulciano. First, Poliziano — founded in 1961, farming 175 hectares and bottling around 845,000 bottles a year, almost all hand-picked, mostly Sangiovese, with two separate microclimates in the same barrel room holding the 2016 and 2017 vintages. Our guide was talkative. The wine was forgiving.
Second stop, Tenute del Cerro, for another tour and a long lunch with three wines plus a dessert wine. Then a wander through Montepulciano itself — we arrived around 3:30, when half the town was closed for the afternoon rest, and it was still one of the most picturesque hill towns we saw.
That night, an Italian chef came to the villa and cooked dinner for us. One of the best evenings of the trip.
Cortona, and a Change of Plans
Day four brought family news that sent Mom and Carl home early, and the rest of us pivoted: Cortona that evening (wine in the square, Gran Caffe Signorelli), then Assisi and Florence from there. The two-hour Italian lunch had already taught us the local art of slowing down. Tuscany helps.
My Rating ⭐⭐⭐⭐⭐ 5 / 5
Highlights
- Cooking school at La Braccesca: bruschetta and hand-made pici
- Ribollita and wild boar pappardelle in Monteriggioni
- Poliziano’s barrel room, two vintages aging in two microclimates
- A private chef cooking dinner at the villa
Good to know
- Hill towns largely close mid-afternoon; plan lunches and shopping for the morning
- A villa base near Cortona puts San Gimignano, Monteriggioni and Montepulciano all within about an hour
- House wine and Chianti Classico are inexpensive and excellent — order the local bottle
More from our 2018 Italy trip: Florence: The David, the Duomo, and Two-Hour Lunches and Venice: Eating Like a Local.
