Tuscany's countryside is a slow-travel region of villas, hill towns, vineyards and truffles. Base in Siena, Pienza or Montalcino and explore by car. May to June and September to October are best.
Good to know
- Rent a car and plan for ZTL (restricted traffic) zones in towns.
- Book wine tastings and cooking classes ahead.
- Stay in an agriturismo for farm-to-table meals.
Eat this
Places the planner can use
Mark places as a must or something to skip. The itinerary is built only from this list; ★ marks the destination’s highlights.
Medieval fortress town and the home of Brunello wine, with tastings in cellars and wine bars.
Romanesque abbey in a quiet valley where monks sing Gregorian chant at services.
Medieval shell-shaped square, striped cathedral and Palio horse-race traditions.
UNESCO landscape of cypresses and farmhouses, the classic Tuscan view.
Renaissance 'ideal city' with cheese shops and a stunning view terrace.
A town with medieval towers rising from the hills; best early morning.
Tasting at family wine estates between Florence and Siena, with a long Tuscan lunch among the vines.
Natural hot springs beside a medieval pool-square, with free thermal waterfalls just below the village.
Walk with a truffle hunter and his dog through oak woods, then taste the harvest in a farmhouse lunch.
See the Leaning Tower of Pisa then cycle on Lucca's intact Renaissance walls, an easy day by train.
Farm dinner with homemade pasta, pecorino and wine, served in a stone farmhouse among vineyards.