About this tour
A nine-hour private circuit through Tuscany's most photogenic hill towns—Siena, San Gimignano and Monteriggioni—with your own driver and guide. You'll travel in a comfortable air-conditioned vehicle through vineyard-dotted countryside, stopping to explore medieval town centres at your own pace. Lunch features local wines and olive oil in a rustic setting. Returns to Florence by evening.
Highlights
- Medieval towers and piazzas of San Gimignano
- Siena's Gothic architecture and Palio traditions
- Monteriggioni's intact stone walls and ramparts
- Rolling Chianti landscape from your own transport
- Tuscan wine and olive oil tasting at lunch
- No shared vehicles—just you, your group and guide
What to expect
You'll spend the morning driving through the Val d'Orcia, stopping to photograph vines and cypress avenues before reaching Siena. Allow a couple of hours to wander the duomo district and shell-shaped piazza. San Gimignano comes next—its cluster of medieval towers rises suddenly across the countryside. The town is compact and steep; wear comfortable shoes. You'll pause for lunch featuring regional wines and cold-pressed oil. Monteriggioni, a fortified village perched on a hilltop, rounds out the afternoon. Expect cobbled streets, minimal crowds compared to Florence, and plenty of photo opportunities. The drive back to Florence takes roughly ninety minutes.
Good to know
Book well ahead during peak season. Comfortable walking shoes essential—towns have steep, uneven streets. Lunch included; inform guides of dietary restrictions when booking. Towns get busy midday; earlier starts mean quieter exploration. Service animals welcome. Infant seats available on request.
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.