Chianti vs Montalcino vs Montepulciano: Which Tuscan Wine Tour Should You Choose?

Three Tuscan wine areas, three Sangioveses, and one question every visitor with a single free day asks: which one? The honest answer depends on where you are sleeping, how much you care about the wine itself, and whether you want a town with your cellars. This guide sets the three side by side, then tells you which to book from Florence, which from Siena, and when it is worth doing two.

The three at a glance

Chianti: the classic, and the easiest

Chianti Classico is the hill country between Florence and Siena, the black rooster on the neck of the bottle, and the Tuscan wine tour most people take first. Estates range from castles to family farms, they are used to visitors, and Greve is 30 to 45 minutes from Florence, so a half-day with two cellars and a tasting of four to six wines is an easy afternoon. The wine is the most approachable of the three: Sangiovese with bright acidity, cherry fruit and a savoury edge, made to drink with food rather than to cellar. If you have one afternoon and no strong opinion, this is the answer. See Chianti wine tours.

Montalcino: the serious one

Brunello is 100 percent Sangiovese from a warmer, drier hill south of Siena, and the law makes it wait: five years from harvest before it can be sold, six for Riserva. The result is Tuscany’s deepest, longest-lived red and its most expensive, and a tasting here is a different experience from Chianti: older vintages, Rosso di Montalcino as the entry point, and estates that take visits seriously and by appointment. It is 50 minutes from Siena and nearly two hours from Florence, which is why wine-focused travellers base in Siena. If the wine itself is the reason for the trip, choose Montalcino. See Montalcino wine tours.

Montepulciano: the town with cellars underneath

Vino Nobile is made from the local Sangiovese clone, aged two years, and sits between the other two in weight and price. What Montepulciano offers that the others cannot is the town: a single Renaissance street along a ridge with cellars carved beneath the palazzi, some reaching Etruscan tombs at the bottom, and tastings you reach by walking downstairs. It combines naturally with Pienza and the Val d’Orcia, and its late-August barrel race, the Bravìo delle Botti, is the most photogenic wine event in Tuscany. Choose it if you want a town day with wine rather than a wine day with a town. See Montepulciano wine tours.

Which one, for which traveller

• First time in Tuscany, staying in Florence, one afternoon: Chianti half-day.
• Wine is the point of the trip: Montalcino, from Siena, full day, two estates.
• You want a beautiful town and a few tastings, not a vineyard marathon: Montepulciano.
• You want the postcard landscape: a Val d’Orcia day that takes in Montalcino or Montepulciano and Pienza. See Val d’Orcia.
• Travelling with people who do not drink: Montepulciano or Chianti, where the towns carry the day.

Can you do two in one day?

Montalcino and Montepulciano, yes: they are 40 minutes apart and the classic Val d’Orcia tour from Siena visits one estate in each with Pienza between them. Chianti and Montalcino, not really: the drive between them eats the day, and each deserves its own. Chianti and San Gimignano is the other easy pairing, from Florence. Three areas in a day is a tour of a van.

Deciding on a day trip from the city? Our pick of the best Chianti wine tours from Florence compares five worth booking.

If you are based in the city, compare the options on our Florence wine tours page.

Frequently asked questions

Is Brunello better than Chianti?

It is bigger, older and more expensive; whether it is better depends on what you like. Chianti Classico Riserva and Gran Selezione compete with Brunello on quality at lower prices.

Is Montepulciano the same as Montepulciano d’Abruzzo?

No. Vino Nobile di Montepulciano is Sangiovese from a Tuscan town; Montepulciano d’Abruzzo is a different grape from a different region.

Which is closest to Florence?

Chianti, at 30 to 45 minutes. Montalcino and Montepulciano are nearly two hours each way.

Which is best from Siena?

Montalcino, 50 minutes away; Montepulciano and the Val d’Orcia are about an hour, and the southern Chianti villages 40 minutes.

Do I need to book wineries in advance?

In Montalcino, almost always; in Chianti and Montepulciano, the larger estates take walk-ins but the good small ones do not. A tour solves it.