Private Cheese and Wine Tour from Siena: Pienza, Montalcino

★★★★★★★★★★ 5.00 (41 reviews) 100% rated it 5 stars

Free cancellationTravelers' pick

1/9

Duration8h

GroupPrivate

LanguagesEN · DE +4

PickupAt your hotel

Cheese from a working farm, Brunello from the cellar, and two hilltowns in one day

A private full-day tour from Siena takes you south through the Val d'Orcia to an organic dairy farm for cheese and olive oil tasting, then to the Renaissance town of Pienza for lunch at your own pace, and finally to Montalcino for a winery tour and tasting of Rosso and Brunello di Montalcino wines. Your English-speaking guide picks you up from your hotel and handles all driving; the route covers eight hours and includes all tastings and farm access.

Step-by-step itinerary

Tuscany cheese and wine tour

Pick up from accommodation
Drive through Val d'Orcia with photo stops
Visit organic farm and taste cheeses
Taste local extra virgin olive oil
Visit Renaissance town of Pienza
Tour Pienza Cathedral and explore streets
Lunch at leisure in Pienza
Drive to hilltop town of Montalcino
Brief visit to Montalcino town
Tour winery cellars and taste wines
Drive back to Siena accommodation

The Experience

The day starts at your accommodation in Siena, where your guide arrives for pickup. The drive south passes through the Val d'Orcia, a UNESCO-protected landscape of rolling hills and cypress-lined roads—the guide stops frequently for photos so you can step out and see why this stretch appears on postcards. The route takes you past Buonconvento and into the countryside before reaching the first stop: a working organic farm where you taste pecorino sheep cheeses and goat cheeses made in their own dairy, plus local extra virgin olive oil. The farm sits on a hillside with views across the neighboring valleys, and the animals are part of what you see.

From the farm, the drive continues to Pienza, a Renaissance town built by Pope Pius II in the 15th century. You have time to walk the quiet streets, visit the Cathedral (free entry), and browse small shops and galleries. Lunch is on your own—the town has restaurants and cafes, and you choose where and when to eat. After Pienza, it's a comfortable drive to Montalcino, a hilltop town known for its red wines and its history as Siena's last stronghold against Florence. A brief walk through the town orients you to the area before you head to a local winery. There you tour the cellars, learn how the wines are made, and taste both Rosso and the region's signature Brunello di Montalcino directly from the producer. The return drive to Siena and your hotel closes the day.

What’s included

Private guide and driver for the full day.
hotel pickup and return to your accommodation in Siena.
access to the organic farm and cheese tasting with local olive oil.
entry to Pienza's Cathedral.
winery tour and wine tasting in Montalcino.
all taxes and fees.

Good to know

Easy physical levelStroller friendlyInfant seats availablePets welcome

Operated by Tuscan Escapes by Papilio SRL

Is this one for you?Book this tour if you want to taste food and wine where it is made rather than in a restaurant, and you prefer traveling as a private group instead of joining others. The eight-hour day is built around the farm and winery visits, so the tastings and cellar tour are the focus, not a quick stop between other sights.