Tuscany & Chianti, Italy

Tuscany & Chianti.

Italy · The rolling hills

Beyond Florence lies the Tuscany of the imagination: a landscape of rolling hills combed with vines and olive trees, lines of dark cypress climbing to honey-colored farmhouses, and medieval towns crowning the ridges. It is a region made for slowing down, for long lunches and longer drives between one beautiful view and the next.

Siena gathers around the shell-shaped Piazza del Campo, one of the finest squares in Italy, while San Gimignano bristles with the medieval towers that earned it the nickname the Manhattan of Tuscany. Between them spreads the Chianti, its cellar doors pouring Sangiovese among the vines, and to the south the Val d'Orcia unfolds in the cypress lanes and golden fields that define the postcard Tuscan view.

This is country best explored by car, with an agriturismo as your base. We map out the cellar visits and hill towns, book the tastings ahead, and leave plenty of room to simply wander, because in Tuscany the road between the sights is half the pleasure.

From
Florence (~1 hr)
Time
2-4 nights
When
Spring & fall (harvest)
Best for
Wine & countryside

Where it is

On the map.

The Tuscan countryside south of Florence, best explored by car.

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What you'll see

On the route.

Siena, Italy

Stop 01

Siena

A medieval city around the shell-shaped Piazza del Campo.

San Gimignano, Italy

Stop 02

San Gimignano

The hill town of medieval towers, the Manhattan of Tuscany.

Chianti vineyards, Italy

Stop 03

Chianti vineyards

Rolling rows of Sangiovese and cellar doors between them.

Val d'Orcia, Italy

Stop 04

Val d'Orcia

The postcard valley of cypress lanes and golden fields.

Know before you go

The practical details.

Getting there

Good to know

Getting there

The countryside is best reached by car from Florence, about an hour to the heart of the Chianti.

Wineries

Good to know

Wineries

Chianti tastings are by appointment at the best estates, so we book your cellar visits ahead.

When to go

Good to know

When to go

The grape harvest runs September into October, when the hills are at their most beautiful and alive.

Where to stay

Good to know

Where to stay

A countryside agriturismo, a working farm with rooms, is the most authentic and relaxing base out here.

Getting around

Good to know

Getting around

A car is essential in this landscape; the hill towns and vineyards are spread across the countryside.

Hill towns

Good to know

Hill towns

Allow time to wander Siena, San Gimignano and the smaller villages without watching the clock.

Let's begin

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