Taste Tuscany: A Wine Journey Through Chianti, Montalcino and Montepulciano

Tuscany is the wine trip people picture before they’ve taken one: cypress-lined roads, stone farmhouses, long lunches under pergolas. The good news is that the reality holds up — and that the region’s great wines all come from one grape, Sangiovese, expressed in very different ways a short drive apart.

Chianti Classico

The hills between Florence and Siena are the historic Chianti zone; bottles from here carry the Gallo Nero, the black rooster seal. Villages such as Greve, Panzano, Radda and Castellina make natural stops, with wineries ranging from medieval castles to small family estates. It’s an easy first day out of Florence.

Montalcino

South of Siena, the hilltop town of Montalcino produces Brunello di Montalcino — 100% Sangiovese, aged for years before release and among Italy’s most celebrated reds. Its lighter sibling, Rosso di Montalcino, is the value find. The town’s fortress has a wine bar for tasting across producers.

Montepulciano

Further east, Montepulciano is one of Tuscany’s most dramatic hill towns, with cantinas carved into the rock beneath its streets. Its wine is Vino Nobile di Montepulciano — not to be confused with the Montepulciano grape grown elsewhere in Italy. Between the two towns lies the Val d’Orcia, the UNESCO-listed landscape of the postcards.

Where to stay

An agriturismo — a working farm stay — is the Tuscan way: meals from the estate, wine from the cellar, a pool among the olives. Two bases work well: Chianti for Florence and Siena days, then the Val d’Orcia for Montalcino and Montepulciano.

When to go

Spring and autumn are best. The vendemmia (harvest) runs roughly September into October. August is hot, and many Italians are on holiday.

Getting around

Tuscany’s roads are beautiful and its tastings generous — a combination that argues for a driver. Private drivers and small-group wine tours are widely available from Florence and Siena. Our no-driving guide compares the options.

Questions visitors ask

Do I need to book winery visits?

Yes, for most estates — even small ones prefer appointments. Walk-in enotecas in the towns are the flexible alternative.

Chianti or Chianti Classico?

Chianti is the wider area; Chianti Classico is the historic heart with stricter rules. For a first visit, stay in the Classico zone. More in our tasting guide.