About this tour
A five-hour private tour departing Florence that threads through Chianti's vineyard-dotted landscape to a working winery, where you'll taste five wines including Chianti Classico and Super Tuscan expressions, before heading to Siena to explore its UNESCO-listed medieval core. The driver navigates you past cypress groves and hilltop villages, then through Siena's Cathedral, Baptistery, and the celebrated Piazza del Campo. Choose the morning (8:30am) or afternoon (3pm) slot.
Highlights
- Five wines tasted at a family-run Chianti winery
- Private car with English-speaking Tuscan driver
- Rolling countryside: vineyards, olives, medieval hamlets
- Siena's Cathedral and UNESCO-protected historic centre
- Piazza del Campo — Italy's most distinctive plaza
What to expect
Your driver collects you from Florence and steers the air-conditioned vehicle south into wine country. Expect 90 minutes of driving through quintessential Tuscan terrain: neat vineyard rows, silvery olive groves, and stone villages clinging to ridges. At the winery you'll spend roughly an hour sampling five wines—reds and whites—with basic commentary on what makes each distinct. Then it's another hour's drive to Siena, where you have time to wander the brick-paved streets, see inside the striped Cathedral and adjoining Baptistery, and stand in the fan-shaped Piazza del Campo. The pace is leisurely; this isn't a rushing checklist tour.
Good to know
Bring comfortable walking shoes for Siena's cobbled streets. Winery tastings don't include a meal, though nibbles usually appear. The vehicle suits wheelchairs and prams. Five hours is tight; you'll see highlights rather than linger. Morning tours avoid afternoon heat.
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.