Val d'Orcia Wine Tour: Montalcino, Pienza, Montepulciano

Taste Brunello and Vino Nobile in three hilltop towns, then return to Florence by evening

A full-day tour from Florence into Val d'Orcia, a UNESCO World Heritage Site, visits three Renaissance hilltop towns: Montalcino (home of Brunello wine), Pienza (the "ideal city"), and Montepulciano (known for Vino Nobile). You taste wine in cellars in both Montalcino and Montepulciano, sample pecorino cheese in Pienza, and have free time to explore each town's streets and views before returning to Florence by coach.

Step-by-step itinerary

Stops and time spent at each2 stops

1. Val d'Orcia2h
2. Montalcino2h

Full-day tour of Val d’Orcia

• Check in at Piazzale Montelungo, Florence
• Drive to Val d’Orcia with guide commentary
• Explore Montalcino and its fortress
• Visit Pienza and stroll its streets
• Discover Montepulciano and Piazza Grande
• Return to Florence by bus

The experience

The tour departs from Piazzale Montelungo, a five- to ten-minute walk from Santa Maria Novella train station, and the drive to Val d'Orcia takes about two hours. Your guide travels with the group throughout the day, offering commentary on the landscape and towns as the coach winds through vineyards, olive groves, and cypress-lined hills. The route itself is part of the experience: the scenery changes gradually from Florence's urban edges into the rolling countryside that defines Tuscany.

In Montalcino, you visit a traditional winery and taste Brunello wines in the cellars: the town's signature wine, aged in underground stone rooms. You have free time to walk the steep alleys of this medieval fortress town and take in views across the vineyards. Pienza, the Renaissance "ideal city," offers a different kind of stop: its streets and piazza are built on geometric principles, and you taste pecorino cheese while exploring its shops and Cathedral. The final town, Montepulciano, sits higher still, with narrow streets lined with Renaissance palaces and a second wine tasting in a historic underground cellar where Vino Nobile is stored. Free time in each town lets you set your own pace: some travelers linger over the views, others browse the local shops.

The return journey gives you time to rest on the comfortable coach as the guide accompanies the group back to Florence. The tour operates in English, Spanish, or Portuguese. You choose your language at checkout. Wine and cheese are available to buy at competitive prices if you want to take bottles or wheels home.

What’s included

• Roundtrip coach transport from Florence.
• expert multilingual guide throughout the day.
• tour of the wine cellars in Montalcino with Brunello tasting.
• tour of the historic underground cellar in Montepulciano with Vino Nobile tasting.
• pecorino cheese tasting in Pienza.
• free time to explore Montalcino, Pienza, and Montepulciano on your own.

Options for this experience

3 options

Tour in English07:45

Tour in Spanish07:45

Tour in Portuguese07:45

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Lasts 11h 30m, runs Monday, Wednesday and Saturday at 07:45, from € 73.60 per person, with a live guide in English, Spanish and Portuguese and with free cancellation up to 24 h before.

Days and timesMonday, Wednesday and SaturdayDeparts at 07:45

Book up toStart time

AgesAdult (9 and older) · Child (3 to 8 years) · Infant (under 3): free

GroupUp to 50

Live guideEnglish, Spanish and Portuguese

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 3 days ago

Good to know

Low physical effortStroller-friendlyPublic transport nearbyNot recommended with heart problemsNot recommended with back problems

Operated by Ciao Florence Tours Srl

Is this one for you?Choose your preferred language (English, Spanish, or Portuguese) at checkout, and the guide will lead the group in that language throughout the day. The fixed itinerary and coach transport mean you don't navigate between towns yourself. The route is designed to fit three towns and two wine tastings into a single full day and return you to Florence by evening.

Traveler reviews

4.58★★★★★★★★★★

55 verified traveler reviews

5 ★44

4 ★6

3 ★0

2 ★3

1 ★2

Read all the reviews ›

Top questions

What languages is the tour guided in?

Live guide in English, Spanish and Portuguese.

Can children come?

Yes. Ticket types: Child (3 to 8 years); Infant (under 3): free.

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What is Brunello wine and where do I taste it on this tour?

Brunello is the renowned red wine of Montalcino, aged in cellars for years before release. You visit a traditional winery in Montalcino and taste Brunello in the wine cellars themselves, where the wine is stored in underground stone rooms.

How much free time do I have to walk around each town?

The itinerary gives you free time in Montalcino, Pienza, and Montepulciano to explore at your own pace: to wander the streets, visit the Cathedral in Pienza, admire the palaces and piazza in Montepulciano, or simply sit with the views. The exact duration at each stop can vary depending on the day's flow.

What is included in the two wine tastings?

One tasting takes place in a winery cellar in Montalcino and features Brunello wines. The second happens in a historic underground cellar in Montepulciano and features Vino Nobile. Both are included in the tour price. Wine and cheese are also available to purchase separately at competitive rates if you want to buy bottles to take home.

Where does the tour pick up and how do I get to the departure point?

The tour departs from Piazzale Montelungo, which is a five- to ten-minute walk from Santa Maria Novella train station in Florence. You check in with the staff there before boarding the coach.

What is the drive like from Florence to Val d'Orcia?

The drive takes about two hours. From the coach, you leave Florence's historic center behind and watch the scenery change into rolling Tuscan hills dotted with vineyards, olive groves, and cypress trees. Your guide provides commentary on the landscape and the towns you're heading toward.

Can I buy wine or cheese to take home?

Yes. The tour includes the possibility of buying Brunello wine, Vino Nobile, and pecorino cheese at competitive prices from the wineries and shops you visit. You can purchase as much or as little as you wish.