Siena, San Gimignano & Chianti wine tour from Lucca: Small group

Vernaccia and Chianti DOCG paired with pecorino at a working wine cellar between two medieval villages.

A 10-hour small-group tour from Lucca visits the medieval towers and ceramic shops of San Gimignano, then a Chianti wine estate for guided tasting and food pairing, then Siena's Piazza del Campo and Cathedral. An expert English-speaking guide leads the route through narrow streets and explains the history of Siena's famous Palio horse race. Transport by air-conditioned bus or minivan, plus olive oil sampling and bruschetta with pecorino cheese, are included. The tour requires a minimum of five passengers to run.

Step-by-step itinerary

Visit San Gimignano, wine tasting, Siena tour

• Arrive at San Gimignano
• Explore medieval towers and ceramic shops
• Taste gelato at Tea with Mussolini location
• Optional visit to San Gimignano history museum
• Visit famous wine cellar
• Guided sampling of Chianti wines with delicacies
• Travel to Siena
• Guided tour of Siena historical center
• Visit Piazza del Campo
• Free time to visit Siena Cathedral

The experience

How do you fit three of Tuscany's most visited villages into a single day without feeling rushed? The answer is a fixed route that starts in San Gimignano, where you walk past the tallest medieval towers and step into ceramic shops that line the narrow streets. The tour includes time to taste gelato at the exact location where "Tea with Mussolini" was filmed, a detail the operator mentions because it matters to the place itself. Between San Gimignano and Siena, you stop at a working wine cellar where the winemaker guides you through a tasting of Vernaccia and Chianti DOCG paired with bruschetta and pecorino cheese, plus a separate olive oil sampling.

Siena is where the day slows down. Your guide walks you through the medieval center on foot, moving through narrow streets until you reach Piazza del Campo, the shell-shaped square that sits among the hills and ranks among Europe's most remarkable medieval squares. The guide explains the secrets of the Palio, Siena's famous horse race, and points out the Palazzo Pubblico and the monumental Cathedral. You get free time to enter sites on your own or simply sit in the square. An optional expert guide for Siena costs 25 euros per adult (children free) and can be arranged at checkout if you want deeper historical detail.

The bus is air-conditioned and the group stays small, which means the pace adjusts and the guide can answer questions without rushing. The tour runs on a fixed schedule and requires a minimum of five passengers. If the group does not meet that threshold, the operator offers an alternative date or a full refund. Bring comfortable walking shoes because the medieval streets and uneven surfaces mean this tour is not suitable for people with walking difficulties. The minimum drinking age for the wine tasting is 18, and you can request vegetarian or celiac accommodations when you confirm your booking.

What’s included

• Transport by air-conditioned bus or minivan.
• expert English-speaking tour guide.
• guided Chianti wine tasting with Vernaccia and Chianti DOCG.
• bruschetta and pecorino cheese pairing.
• olive oil sampling at the wine estate.

Before you book

Days and timesThursday and SundayDeparts at 08:15Last departure this season: 29 Oct

AgesAdult (11 to 90 years) · Child (3 to 10 years) · Infant (under 3): free

GroupUp to 18

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 3 days ago

Good to know

Moderate physical levelStroller friendlyPublic transport nearbyNot for back problemsInfants must sit on laps

Operated by Come See Italy - Day Tours

Is this one for you?The 10-hour duration leaves room for a leisurely lunch on your own in either village, but rules out combining this tour with another full-day activity in Lucca. Small-group size means the pace adjusts for questions and the guide can point out details a larger bus would miss, though the medieval streets and uneven surfaces require comfortable walking shoes and at least moderate fitness.

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Top questions

Can children come?

Yes. Ticket types: Child (3 to 10 years); Infant (under 3): free.

What exactly is Vernaccia, and is it only made in Chianti?

Vernaccia is a white wine from the Chianti region, and the winemaker at the estate you visit will introduce you to his version during the guided tasting. It is paired with local cheese and bruschetta as part of the tour's wine sampling.

How much free time do you get in San Gimignano and Siena?

San Gimignano gives you time to walk the ceramic shops and taste gelato at the filming location for "Tea with Mussolini," plus the option to enter the small history museum on your own. In Siena, you have free time after the guide leads you through the historical center and Piazza del Campo to explore the Cathedral or sit in the square.

Is the 10-hour tour one continuous bus ride, or do you get out and walk?

You travel by air-conditioned bus or minivan between the three villages, but once you arrive in each one, you walk through the medieval streets and squares on foot. The guide leads you through Siena's narrow center to Piazza del Campo. The uneven surfaces mean comfortable walking shoes are essential.

Can you add a guide just for Siena if you want more history?

Yes, an expert guide for Siena can be added at checkout for 25 euros per adult. Children go free. This is optional and paid on the day of the tour, so you decide after booking whether you want the deeper historical detail.

What happens if fewer than five people book the tour?

The tour requires a minimum of five passengers to run. If that threshold is not met, the operator will offer you an alternative date or a full refund, so you will know before the tour date whether it is confirmed.