Medieval Tuscany
Siena · Monteriggioni · Val d'Elsa · San Gimignano · Siena
- Duration
- about 7 hours
- Where we start
- Siena · Florence · My hotel
- Group
- Private, just your group
- Car
- Chosen together
- Languages
- English, Italian
The experience
This is the day of the towns, in a classic car, and you drive. From Siena to Monteriggioni, along the Val d'Elsa, to San Gimignano, with lunch. The towers are the reason. The cellar days are a different day.
- Route: Siena → Monteriggioni → Val d'Elsa → San Gimignano → Siena
- Lunch: Linfa or Da Pode
- A private itinerary, for your group only
Highlights
San Gimignano
The towers are the reason for the day.
Monteriggioni and the Val d'Elsa
The road that gets you there, from Siena.
Lunch
In the town, at Linfa or Da Pode.
You drive
A classic car. The cellar days are another day.
Every route is driven by our team before it is offered to anyone. On the day, the plan bends to the weather, the light and your pace.
Getting here, and what to know before you book
Which airport should I fly into for Tuscany?
Florence (FLR) is the closest, about an hour from the Chianti hills and from Siena, and is reached with one connection through a European hub. Pisa (PSA) is a similar distance from the coast. If you would rather fly nonstop from the United States, Rome Fiumicino (FCO) is roughly three hours away by road and Milan Malpensa (MXP) around three and a half.
How far in advance should I book?
Late spring and early fall are the busiest windows, and the cars and the wineries for a given date are finite. As soon as your travel dates are firm, write to us: the team replies within one hour, Monday to Friday, so you will know quickly whether the day you want is open.
Do I need an International Driving Permit?
Italy asks drivers holding a non-EU license to carry an International Driving Permit alongside it. In the United States you get one from AAA, usually the same day, and it is valid for a year. Bring both documents on the day, together with a passport and a credit card in the driver's name.
Where do the Tuscan days start, and how do I get there?
Departures are from Siena or Florence; the Siena days meet at Villa Ermellina, Via Custoza. Most guests base themselves in Florence, in Siena or at a hotel in the countryside — tell us where you are staying when you book and we will agree the meeting arrangements from there.
What time is it in Tuscany, and when will I hear back?
Italy runs on Central European Time: six hours ahead of New York, nine ahead of Los Angeles. A message written in the American morning arrives inside the Italian working day, so you will normally have an answer before your afternoon.
One team, from first idea to the road
Private, never shared
Every day is built for one group. No strangers, no fixed departures.
One local team
We live between Siena and the Val d'Orcia, and we answer the phone.
Driven before it's offered
We drive each route ourselves before offering it to anyone.
You may also like

Dolce Vita in Chianti
Siena, Florence or your hotel · Castello di Brolio · the roads of Chianti · Radda in Chianti · Castellina in Chianti · return
Explore
Dolce Vita in Val d'Orcia
Siena · San Quirico d'Orcia · Pienza · Bagno Vignoni · Siena
Explore
Heart of Chianti
Siena, Florence or your hotel · Castello di Brolio · Gaiole and Radda in Chianti · Castellina in Chianti · return
Explore
Brolio Castle & Chianti Classico
Siena, Florence or your hotel · Castello di Brolio · return
ExploreTell us how you picture it
Send us dates, number of guests and preferences: we'll prepare a tailored proposal with the estimate and conditions, once availability is verified.