A full‑day private drive from Rome through Val d'Orcia visiting Montepulciano, Pienza and Montalcino. Experience Renaissance streets, hilltop views and world-class wineries with guided time in each town.
More ways to explore the area's outdoor wonders
You step out of a climate‑controlled Mercedes as the road opens onto a ribbed expanse of ochre hills and cypress lines—Val d'Orcia’s slopes rolling away like pages in a field guide. The air smells faintly of sun‑warmed grass and fermenting grapes; a distant church bell marks time while vineyards press against fortified town walls.
Difficulty
easy
Duration
10–12 hours
Fitness Level
Suitable for most travelers who can manage walking on uneven cobblestones and short uphill sections
Wildlife
History
Pienza was redesigned in the 1400s under Pope Pius II and is a noted example of Renaissance urban planning; Montalcino and Montepulciano grew as fortified hill towns tied to regional trade and viticulture.
Conservation
Tourism pressures vineyards and small roads—support local producers, follow posted access rules, and limit waste by using refillable bottles and staying on public paths.
Reserve your spot on the Tuscany Tour: Montepulciano, Pienza & Montalcino today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Book winery visits in advance
Many small producers operate by appointment—reserve tastings ahead to guarantee cellar access and guided pours.
Wear stable footwear
Cobblestones and steep alleys require shoes with good grip; avoid new soles that can slip on wet stone.
Bring a refillable bottle
Bottled water is provided but having your own reduces waste and keeps you hydrated during walks between towns.
Plan for long travel time
This is a long day with transfers from Rome—expect 10–12 hours door‑to‑door and limited downtime between stops.
Comfortable walking shoes
Provides traction on cobblestones, terraces and uneven town streets.
Sun hat and sunglasses
Protects you during midday vineyard walks and open viewpoints.
summer
Light packable jacket
Useful for cooler mornings, terraces and sudden breezes on hilltops.
spring
Reusable water bottle
Staying hydrated is important during a long day of walking and tasting.