Cancellation Policy
Cancellations made 15 or more days in advance of your tour date are fully refundable, minus our 3% credit card processing fee. See our complete Cancellation Policy for more information.
Cancellations made 15 or more days in advance of your tour date are fully refundable, minus our 3% credit card processing fee. See our complete Cancellation Policy for more information.

The rolling hills of the Val d'Orcia are what many people picture when they think of Tuscany, and a day cruising through the towns and countryside of this beautiful part of the world is always unforgettable. I've lived here all my life and I never tire of it!
So, let's set off on a day together visiting the lovely and atmospheric hilltop towns and bucolic landscapes of my home region.
How we spend the day is entirely up to you, but my suggestion is always to mix scenic drives with a wander through a few towns, plus a tasting at a fantastic local winery. And whenever we get hungry, we'll pick a spot for lunch where we can sample more local products and dishes.
Of course, the day is yours, so you tell me what you'd like to do: we can spend more time exploring the charming little villages and skip the winery entirely, or we can do the reverse, spending less time in the towns and adding a second winery into the itinerary.
So that you have an idea of what's possible, typically, a tour can either include 3 towns and no winery visit or 2 towns and 1 winery visit and tasting. You can choose to visit a combination of the following towns:
*Please note: Serena's vehicle can accommodate up to 4 participants. For groups of 5-8, she can arrange for a driver and luxury minivan at an additional cost of $550 USD. If you have a group of more than 4, please send Serena a message.
Tours can begin from your accommodation in the area around Montepulciano, Pienza, and Montichiello. For pick-up and drop-off in other areas, please reach out for a price quote.
Cancellations made 15 or more days in advance of your tour date are fully refundable, minus our 3% credit card processing fee. See our complete Cancellation Policy for more information.
Approximately 8 hours
This tour can start at any of the following times: 9:00 AM or 10:00 AM
This tour can be delivered in English or Italian
This private tour can accommodate parties of up to 4 people
This tour costs a flat fee of $590.00 USD
Private round-trip transportation is included in the cost of this tour
Max 8 people | 4 hours
5.0 rating from 26 reviews
5.0 rating from 26 reviews