Val d'Orcia & Montalcino: Private Tuscany Day Tour from Florence

Three Medieval Towns & a UNESCO Valley in One Day from Florence

You're picked up from your Florence hotel at 9am and driven through three medieval towns (Montepulciano, Pienza, and Montalcino) plus the Val d'Orcia UNESCO landscape, with a local guide handling all the stops and timing. The day includes winery tastings and guided walks through each town's main sights and hidden corners, with transportation and bottled water covered. You return to your hotel in the evening.

Step-by-step itinerary

Stops and time spent at each

1. Val d'Orcia2h
2. Montalcino2h

Explore Val d'Orcia and medieval towns

• Meet guide at hotel at 9 am
• Visit Montepulciano and walk streets
• Taste local wine and food at winery
• Travel to Pienza and explore Renaissance sites
• Enjoy scenic views and photos in Val d'Orcia
• Tour medieval village of Montalcino
• Return to hotel with Val d'Orcia views

The experience

The drive out of Florence takes about an hour, and then the landscape just opens up: rolling hills, cypress trees standing alone like punctuation marks, vineyards that seem to go on forever. Your guide meets you at your hotel at 9am and handles all the navigation, which means you're free to actually look at what's happening outside the window instead of squinting at a map. The first stop is Montepulciano, a town that sits 600 meters up on a hilltop, and the moment you step into the old streets, you understand why people paint this place. The buildings are narrow and tight, the stone is warm-colored, and when you reach the top, the view down into the valley is the kind of thing that makes you understand why Renaissance painters kept coming back to Tuscany.

From there, the tour moves through Pienza: a UNESCO site since 1996, built according to Renaissance ideals about how a city should be organized, which sounds dry until you're actually standing in the main square and realizing that every angle, every building, every perspective was planned. Your guide walks you through the main attractions and the quieter corners, the ones that don't make it into every guidebook. Then comes the drive through Val d'Orcia itself, the UNESCO heritage landscape that's been shaped by centuries of farming and living, not just a pretty view, but a place where people actually work. You'll have time to stop for photos, and honestly, you'll need it. After Pienza, the final stop is Montalcino, famous for Brunello wine since the 14th century. The village has stayed almost unchanged for centuries, and from the top where the castle sits, you can see why people chose to live here. The landscape just keeps rolling away in every direction.

The winery visit happens in Montepulciano, and it includes wine tasting and typical local food: lunch itself costs extra, but the tasting is part of the package. Your guide shares the history as you move through the towns, the stories behind the architecture and the wine, the way the land has been organized. The whole day runs from 9am until you're back at your hotel in the evening, and the private vehicle means no waiting for other groups, no fixed stops that don't interest you, no rushing because a bus is on a schedule.

What’s included

Your day includes hotel pickup at 9am, private transportation throughout, guided tours of Montepulciano, Pienza, and Montalcino, a winery visit with wine and food tastings, bottled water, and return to your hotel in the evening. Lunch beyond the winery tastings costs extra.

Options for this experience

2 options

Full-day Tuscany tour for up to 6 peopleGuide in English or Italian · 08:00, 09:00 and 10:00Minivan; pickup is included

Full-day private tour of Val d'Orcia: the best of TuscanyGuide in English, Italian or Russian · 10 departure times: the first at 07:00, the last at 16:00Pickup is included

You pick the guide language when booking.

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

Before you book

Days and timesEvery day10 departure times: the first at 07:00, the last at 16:00

Book up to1d before

AgesAdult (21 and older) · Infant (under 21)

GroupPrivate

Live guideEnglish, Italian and Russian

Meeting point and pickupHotel pickup included.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 4 days ago

Good to know

Low physical effortInfant seats availablePets welcomePublic transport nearbyInfants must sit on laps

Operated by Events in Italy

Is this one for you?Book this if you want to see the main Tuscan highlights (medieval towns, UNESCO landscapes, and local wine) without renting a car or piecing together public transport. The private guide and fixed pickup time mean you show up at your hotel and the day is already planned.

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Top questions

What languages is the tour guided in?

Live guide in English, Italian and Russian.

Can children come?

Yes. Ticket types: Infant (under 21).

How long is the full day tour?

The tour runs from 9am hotel pickup until evening return, typically 8–9 hours including all stops and travel time.

Is lunch included?

Lunch is not included in the base price. The winery visit includes wine tasting and typical local food, but a full meal costs extra.

Can I book this tour if I'm staying outside Florence?

Hotel pickup is included, so yes. The guide will collect you from your accommodation in the Florence area at 9am.

What's included in the price?

Private transportation, guided tours of Montepulciano, Pienza, and Montalcino, winery visit with tastings, and bottled water.

Can I visit the wineries and taste wine if I'm driving?

Yes, you're in a private vehicle with a driver, so you can enjoy wine tastings without worrying about driving yourself.

What if I want to skip one of the towns?

The itinerary is set, but your guide can discuss any preferences when you meet. The tour is designed to cover all three towns and Val d'Orcia in one day.