What's included, and what costs extra?

Private minivan transport, driver, and guided town access are included. Lunch, wine tastings, vineyard visits, and museum entries (if desired) are separate. Wine-tasting experiences can be booked as an add-on.

How much of the day is spent driving vs. exploring?

Approximately 4 hours are spent on the road from Rome (round-trip), leaving 4–5 hours for walking, sightseeing, and meals in Pienza and Montepulciano.

Can I customise the tour—e.g., skip one town or add a vineyard visit?

Yes. This is a private tour, so your driver and itinerary are flexible. Confirm customisations (vineyard bookings, additional stops, timing) when you book.

Is this tour accessible for people with mobility issues?

Both Pienza and Montepulciano are built on hills with steep, uneven cobblestone streets and many stairs. Accessibility is limited; discuss any mobility concerns with the operator before booking.

What's the group size, and do I share the vehicle?

This is a private tour, typically for up to 6–8 people per minivan. You're not sharing with other tour groups, but confirm group limits when booking.

Comfortable walking shoes, sunscreen, water, a light jacket (mornings and evenings can be cool), and a camera. Bring cash or cards for meals and optional activities; rural towns have limited ATMs.

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Pienza and Montepulciano by Tuscan Hills from Rome Private Tour

(3)

Rome, Italy

Bus & Minivan ToursLuxuryCultural ToursFood & Drink Tours

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About this activity

Escape Rome for a full-day private tour through UNESCO-listed Val d'Orcia, visiting the Renaissance hilltop towns of Pienza and Montepulciano. This curated journey blends art, food, and landscape—three cornerstones of Tuscan culture—with personalised transport and optional wine tastings.

This is one of our best-selling daily excursions from Rome, because it allows travelers to discover and enjoy one of the most beautiful countryside in the world, the famous Valle d'Orcia of Tuscany, Unesco Heritage. Moreover, you will be taken to visit two of the most beautiful towns of the Tuscany region, Pienza and Montepulciano. This tour perfectly combines Art, Food, and Relax, the principles of a good life.
By specific request, we can organize a wine-tasting experience that will make the day trip even more interesting!

Highlights

✓Explore Pienza's perfectly planned Renaissance centre, designed as an ideal city by Pope Pius II
✓Wander Montepulciano's medieval streets and Renaissance palaces with panoramic views across rolling vineyards
✓Drive through Val d'Orcia's UNESCO World Heritage landscape of cypress-lined roads and sculptural hills
✓Taste local Pecorino Romano cheese and regional wines (upgradable)
✓Flexible itinerary: customise stops and pace in a private vehicle

Insider tips

★Book the wine-tasting upgrade in advance if you want a structured sit-down experience; vineyard visits can be arranged at select estates
★Wear comfortable walking shoes—both towns involve climbing narrow cobbled streets with uneven surfaces
★Visit Pienza's Piazza Pio II early in your day to beat coach tours; it's the true masterpiece and best photographed in morning light

Good to know

•10-hour total duration includes ~4 hours driving from Rome; plan 3–4 hours for town exploration and meals
•Private minivan transport means flexible departure times and stops; confirm pickup location in Rome when booking
•Lunch is not included; allow time and budget for meals in town (expect €12–25 per person for casual dining)
•Summer heat can be intense—bring water, sunscreen, and hat; spring (April–May) and autumn (September–October) offer ideal temperatures

Who it's for

Art and architecture enthusiasts drawn to Renaissance design and urbanismSlow-travel foodies seeking authentic regional cheese, wine, and landscapeCouples and small groups wanting flexible, personalised itineraries away from tour-bus routesPhotographers chasing iconic Tuscan scenery and golden-hour light

Best time to visit

April–May and September–October offer perfect weather for walking hillside towns without summer crowds or winter closures. Early morning departures (typically 7–8 AM) maximise daylight and minimise traffic around Rome.

Frequently asked questions

Reviews

(3)

Sam T.

May 2026

our guide Wei really knew their stuff and a stop the guide added on the fly was the highlight, and blew our Rome one out of the water.

Priya A.

Jan 2026

our guide Nadia really knew their stuff and a little local spot off the usual route was the highlight, and blew our Crete one out of the water.

Emma E.

Aug 2025

our guide Hana couldnt do enough for us and a little local spot off the usual route was the highlight, and fine even with my dodgy knee, and came away with 200+ photos.

from€1,150/ person

4.8 · 66 reviews on Trustpilot

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