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Towers, Frescoes and Food: Parma to Tuscany

The history along a week between Parma and Siena: a fortress in the Parma hills, balsamic attics in Modena, a Chianti stronghold and a town in the Val d Orcia.

Juniper Latitude4 min readUpdated 2026

Towers, Frescoes and Food: Parma to Tuscany

In 1448, Count Pier Maria Rossi raised the fortress of Torrechiara above the Parma hills, and its golden chamber still glows under frescoed vaults today. It stands within a short drive of a dairy where Parmigiano Reggiano is stirred in copper cauldrons at dawn, and that combination, a medieval monument beside a working food tradition, is what a week between Parma and Tuscany keeps delivering. This article follows the route through the centuries, ending each era at a building you can still walk into.

The fourteenth and fifteenth centuries: strongholds of the food valley

The hills south of Parma were frontier country between rival lords, and the stone they left behind still organises the landscape. Torrechiara is counted among the finest fortresses of its kind in the country. In Chianti, the fortress called La Rocca rises from the main square of Castellina, its fourteenth century tower open for views over the vineyards; below it runs a vaulted street where soldiers once patrolled and where shops now sell handmade leather. Both towers belonged to the same story, the league of Chianti towns defending their territory against nearby Siena, and the wine those towns traded is still poured at lunch in Castellina's arcaded streets. The food that made the Parma plains famous, the cheese and the hams, matured in the shadow of the same border wars, and producers still welcome visitors in the rooms where their grandparents worked.

A chronicler of the Chianti league recorded that its towns banded together to hold the road between Florence and Siena, and the stone gates of Castellina still face that road today.

Around 1500: frescoes, humanists and a redesigned hilltop

Turning from defence to art, the Benedictine abbey of Monte Oliveto Maggiore sits among pine and oak in the Siena clay hills, and its great cloister carries a fresco cycle of the life of St Benedict painted by Luca Signorelli and Sodoma at the turn of the sixteenth century. The monks still chant in the abbey church. A few kilometres west, Pienza shows the Renaissance at its most confident: in the fifteenth century the humanist Enea Silvio Piccolomini, who became Pope Pius II, rebuilt his birth village on a ridge above the Val d'Orcia as a model of elegant town planning, and the UNESCO-listed result, its cathedral facing a piazza framed by a palace and a well, is walked through today much as he imagined it. Siena itself, a rival republic to Florence for centuries, keeps its medieval shape intact around the shell-shaped Campo, where the Duomo and baptistery anchor a walking visit.

Between the wars of the cities: wine as heritage

The rivalry that built towers also planted hills. Montalcino's castle, a bastion of the Sienese republic in its long contest with Florence, now overlooks vineyards that produce one of the country's most prestigious reds, and a masterclass with a local winemaker beneath its walls ties the wine to the stone. Montepulciano, Montalcino and Chianti all grew rich on the same trade, and the cypress-lined roads of the Crete Senesi that link them follow routes older than any of the labels. Tasting rooms occupy granaries, convents and palazzi, so every glass comes with a building attached.

The twentieth century: engines and vinegar in Modena

East of Parma, Modena holds two traditions that ripened in modern times. Traditional balsamic vinegar ages for years in wooden barrel sets in family attics, and a private visit to a producer explains the technique and the taste that supermarket versions only imitate. The city is also the home of the most famous name in motorsport: the Enzo Ferrari museum wraps the house where Enzo Ferrari was born in a striking yellow gallery interiors by the architect Jan Kaplicky, and the exhibits trace a century of racing. A lunch of fresh pasta dressed with aged balsamic sits comfortably between the two.

  • Torrechiara fortress above the Parma hills, built in 1448 and open to visitors
  • The fourteenth century tower of La Rocca in Castellina in Chianti
  • Signorelli and Sodoma frescoes in the cloister of Monte Oliveto Maggiore
  • Pienza, the fifteenth century model town of Pope Pius II in the Val d'Orcia
  • The Enzo Ferrari museum in Modena, built around his birthplace

What the eras leave on the table

Each historical layer in this part of the country comes with a dish. The fortress era gave the Parmigiano dairies and the prosciutto curing rooms of the Parma hills; the Renaissance towns gave Pecorino aged in the Val d'Orcia and the sweets of Siena's bakeries, such as ricciarelli, cavallucci and panforte; the modern era gave the balsamic cellars of Modena. A week that begins at Bologna airport and ends there again, with three nights in the Parma hills and three in Tuscany, can gather all of it without a single long drive, and the last morning, spent over Sienese hams and bread salads or over the towers of San Gimignano, closes the circle back at Torrechiara's stone.

Written by the Juniper Latitude team. Routes are checked on the ground and pages are edited in place when something changes. Spotted an error? Tell us and we will fix it.

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