About this tour
Spend nine hours exploring Tuscan wine country and medieval towns on a private guided drive from Montecatini. Your English-speaking driver takes you through rolling Chianti vineyards to discover stone villages and the remarkable hilltop settlement of San Gimignano, famous for its tower-studded skyline. Travel in a comfortable Mercedes minivan, stopping where you choose to taste local wines, browse village piazzas, and eat where locals do. This is a customised itinerary—move at your own pace through some of Italy's most photographed countryside.
Highlights
- Chianti countryside villages and working wine estates
- San Gimignano's medieval towers and narrow cobbled streets
- Private Mercedes transport with fluent English-speaking guide
- Flexibility to linger at wineries, restaurants, or viewpoints
- Hotel-to-hotel pickup and drop-off from Montecatini
- Bottled water throughout the day
What to expect
Your driver collects you from your Montecatini accommodation and heads south into vineyard-quilted hills. You'll stop in Chianti villages—places like Greve or Castellina—where narrow streets open onto quiet piazzas, antique shops, and family-run enotecas. If you want to visit a winery, your guide can arrange it; tastings cost extra and are booked on the day. By mid-afternoon you reach San Gimignano, perched on a ridge with fourteen towers piercing the sky. Allow two to three hours to wander, eat lunch (your choice of restaurant), and soak in the Renaissance atmosphere. The drive back to Montecatini takes roughly an hour.
Good to know
Wine tastings and meals are not included—budget accordingly. Museum and monument entry fees are separate. Infant car seats available on request. Service animals welcome. Suitable for all fitness levels, though San Gimignano involves uphill walking on uneven medieval streets.
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.