The Expat Field Notes

Field Notes from the Valdichiana

My corner of eastern Tuscany — and a slice of Umbria. The towns, tables, wineries, and terme I'd send a friend to, around Cortona, the Valdichiana, and Lake Trasimeno.

How to use this

One town, one long lunch, one good bottle

When people find out we live here, the question is always the same: where do you actually go? Not the bucket-list version — the real one. So I wrote it down. It leans slow on purpose. Pick one thing a day and let the afternoon run long; the magic of this place is never in seeing everything.

A living list — real places, organized the way I'd plan a week. The best entry on any list is the one you find yourself.

No. 01 — The Towns

Where to point the car

All within an easy drive of Cortona — a couple slip just over the Umbrian line, around Lake Trasimeno. Go early or late; the light and the quiet are both better at the edges of the day.

Cortona

15 min · home base

The town Under the Tuscan Sun made famous, and still worth it. Steep streets, Etruscan walls, a piazza made for a slow aperitivo. Climb to Santa Margherita for the view.

Castiglione del Lago

35 min · borgo più bello

On a spur over Lake Trasimeno, just across the Umbrian line. One of Italy's official borghi più belli — walled, soft lake light, sunsets worth timing dinner around.

Montepulciano

40 min · wine

A ridge town stacked in honey-colored stone, famous for Vino Nobile. Walk up to Piazza Grande, then duck into a cellar carved into the hillside for a tasting.

Pienza

50 min · pecorino

The “ideal Renaissance town,” small enough for an afternoon. Come for the pecorino — aged in ash, hay, walnut leaves — and the view down the Val d'Orcia.

Panicale

40 min · the quiet gem

A tiny walled borgo above Trasimeno most people miss — a Michelin-recognized kitchen and some of the best olive-oil tasting around. Go for the view, stay for lunch.

Arezzo & Anghiari

30–50 min · market days

Arezzo for the antiques market and Piero della Francesca's frescoes; Anghiari — a borgo più bello — for one of Italy's most beautiful medieval streets.

No. 02 — The Tables

Where to eat well

Family-run, local, and worth booking ahead — especially in summer. Ask for the pici, the hand-rolled pasta of this exact valley.

La Bucaccia

Cortona · pasta, cheese & salumi

In a medieval cellar — house-made pici, a serious pecorino board, and beautiful cured meats. The full Tuscan table. Book ahead; it fills.

Osteria del Teatro

Cortona · a little dressed up

For the night you want candlelight and a tablecloth without leaving the old town. Classic Tuscan plates, done with real care.

Il Muzzicone

Castiglion Fiorentino · the local table

Right on the piazza in town — bistecca alla fiorentina and pasta fatta a mano. Where you go for exactly what locals eat.

La Dogana Enoteca

Valdichiana · farm to table

A delicious, seasonal menu that changes with what's good that week, and a wine list to match. Worth the drive out.

No. 03 — The Bottles

Where to taste

Three appellations meet around here: Vino Nobile di Montepulciano, the bold Cortona Syrah, and the everyday-lovely Valdichiana DOC. Always call ahead to book a tasting.

Buccelletti Casali & Cantina

Castiglion Fiorentino · since 1625

A family that's farmed this valley since 1625 — now woman-owned and run. Taste in their beautifully restored olive mill, with villas and pools looking out over the valley. Valdichiana DOC, and one of ours.

La Pievuccia

Castiglion Fiorentino · organic

Small, hands-on, fully organic — five hectares of vines plus their own oil, Vinsanto, and honey. The pool and hot tub look straight out at the Montecchio castle. Warm, personal tastings, minutes from Cortona.

Avignonesi

Montepulciano · biodynamic

A gorgeous, serious estate farming biodynamically across the Cortona–Montepulciano line. Famous Vino Nobile and a legendary Vin Santo. The tour to splurge on.

Poderi Boscarelli

Montepulciano · family

A small, beloved family winery making some of the most quietly respected Vino Nobile in the area. Intimate tastings, real warmth.

No. 04 — Where to Stay

Sleep in the countryside

Skip the city hotel. Stay at an agriturismo — a working farm that hosts — and wake to olive trees and a pool instead of a parking garage.

Buccelletti Casali

Castiglion Fiorentino · wine resort

Villas and pools overlooking the valley on a family wine estate worked since 1625, woman-owned and run. Stay where the bottle is made — and taste in the restored olive mill.

La Pievuccia

Castiglion Fiorentino · organic B&B

An organic farm-stay with its own winery, a pool and hot tub framing the Montecchio castle, and a local breakfast. Quiet and personal, a few minutes from Cortona.

Agriturismo I Pagliai

Cortona · pool & table

Lovely rooms, green grounds, an outdoor pool, and dinner on site. An easy, gracious base near Cortona for a first trip.

Le Terre dei Cavalieri

Cortona · 18th-c. estate

An 18th-century farmhouse with a stunning pool, set among wheat fields and sunflowers. The romantic choice.

No. 05 — The Terme

Where to soak it off

Tuscany sits on volcanic water, and a long soak is the most Tuscan way to end a day of towns and tasting. From easy public baths to five-star spa, here's where to go.

Rapolano Terme

50 min · the easy soak

Two thermal bath houses on the edge of the Crete Senesi, water gushing out around 39°C. The relaxed, unfussy choice — go for a long afternoon.

Adler Thermae

1 hr · the splurge

A five-star spa resort beside Bagno Vignoni, fed by mineral water that rises at 50°C. Pools, saunas, treatments — the day you book to be properly spoiled.

Posta Marcucci

1 hr · the classic

In Bagno Vignoni — the beloved Val di Sole outdoor thermal pool, looking straight across the Val d'Orcia. Time it for golden hour.

Free & natural

bonus · bring a towel

Bagno Vignoni has open-air spots, and the cascades at Bagni San Filippo run hot straight out of the hillside. Go early and it's all yours.

If you only have a few days

How to spend a slow week

Land in Cortona. Do nothing the first day but walk the walls and have an aperitivo in the piazza as the light goes gold.

One long lunch at La Bucaccia, then a slow afternoon. The meal is the plan, not a stop on the way to one.

A winery morning close to home — book Buccelletti or La Pievuccia — and let the tasting drift into lunch.

Pienza for pecorino, then the Val d'Orcia view at golden hour. Buy the cheese; you'll want it later.

A market morning in Arezzo or Anghiari. Go for nothing in particular and come back with too much.

A long soak at the terme — Rapolano or Bagno Vignoni. The day your shoulders finally drop.

Dinner at the agriturismo on your last night — whatever the kitchen made. The most Tuscan meal of the trip.

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