Plan my experience
Classic Car Journeys

Medieval Tuscany

Siena · Monteriggioni · Val d'Elsa · San Gimignano · Siena

Private · just your groupReply within 48 hoursTuscany
Duration
about 7 hours
Where we start
Siena · Florence · My hotel
Group
Private, just your group
Car
Chosen together
Languages
English, Italian
Overview

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
The journey

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.

Planned here, shaped by you

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.

No payment now · Reply within 48 hours

Planning from the US

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.

Why Rocca d'Italia

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.

Request

Tell 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.