About this tour
A 12-hour private excursion from Rome into Tuscany's countryside, combining two medieval towns with scenic driving through vineyards and hills. Your own driver whisks you through Siena's Gothic streets and San Gimignano's distinctive tower-topped skyline, with the option to stop at a Chianti winery for tastings. Hotel collection and return included.
Highlights
- Medieval Siena with its famous shell-shaped piazza
- San Gimignano's 14 surviving medieval towers
- Rolling Tuscan farmland, vineyards, olive groves
- Optional Chianti winery visit with food pairing
- Private vehicle and driver throughout the day
What to expect
You'll be collected from your Rome accommodation and driven south into Tuscany's countryside for roughly three hours. The landscape shifts gradually from plains to undulating hills dotted with cypress trees and stone farmhouses. Once in Siena, you have time to navigate the medieval core on foot—the cathedral, the contrada neighbourhoods, Piazza del Campo. Afterwards you'll head north to San Gimignano, a compact town where towers rise dramatically above terracotta roofs; it's easily covered in an hour or two. If you've opted for the winery stop, this typically happens between the two towns. Expect plenty of driving time; the day is less about rushing between sights and more about savouring the Tuscan landscape.
Good to know
Wear closed shoes with good grip for cobbled streets. Dress code is strict at churches and some museums—shoulders and knees must be covered. Bring water and sun protection. Food and drink are not included, so budget for meals in both towns. The 12-hour timeframe includes driving, so actual time in each location is limited.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.