San Gimignano and Winery Tour from Pisa: Tuscan Wine and Lunch

Step inside San Gimignano’s medieval streets, then unwind with Chianti wine and a light Tuscan lunch.

A small group or private tour from Pisa to the medieval hilltop town of San Gimignano in the heart of Tuscany, with stops to walk the ancient towers and stone streets, then a winery visit for Chianti tasting and a light Tuscan lunch. The tour runs 7 to 8 hours and includes transport by air-conditioned minivan, a live guide in English or Italian, and all food and wine. Children under 18 cannot participate in the wine tasting.

Step-by-step itinerary

Visit San Gimignano and winery

• Travel from Pisa to San Gimignano
• Walk in medieval San Gimignano village
• Enjoy light lunch and wine tasting
• Relax at the winery

The experience

The minivan picks you up in Pisa and heads into the Tuscan countryside toward San Gimignano, a medieval town built on a hilltop and known for its towers, so many that locals call it the Manhattan of Tuscany. You'll walk through the village on foot, moving through streets and piazzas that have stayed largely unchanged for centuries, with views across the rolling hills from the high points of the town. The guide points out the history woven into the stone and the way the towers still dominate the skyline.

After time in San Gimignano, the group moves to a winery in the Chianti region. There you'll taste a variety of wines in a relaxed setting and sit down to a light Tuscan lunch. The meal and the tasting happen together, so you're eating and drinking at the same pace. The winery atmosphere is designed to be unhurried. This is not a rushed stop.

You travel the whole day in an air-conditioned minivan, which means no navigating rental cars or public buses through the Tuscan hills. The guide handles the route and the timing. If you have dietary restrictions or food allergies, let the operator know when you book so the lunch can be adjusted. Infants and small children can bring a pram or stroller for the walking portions of San Gimignano, and specialized infant seats are available in the van if needed.

What’s included

• Transport by air-conditioned minivan from Pisa.
• a live guide in English or Italian.
• entry to San Gimignano and time to walk the medieval town.
• Chianti wine tasting at a winery.
• a light Tuscan lunch.

Options for this experience

2 options

Private tour optionGuide in English or Italian · 09:00

Tour for small groups of up to 12 peopleGuide in English or Italian · Available from 24 Oct 2027Small group tour departing from Pisa

You pick the guide language when booking.

You see the exact price of each option when you check availability.See dates & prices

Before you book

Days and timesEvery dayDeparts at 09:00

Book up to1d before

AgesAdult (10 and older) · Child (2 to 9 years) · Infant (under 2): free

GroupUp to 8

Live guideEnglish and Italian

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 today

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by Bellaitalia Tour

Is this one for you?Choose the small group option if you're comfortable meeting other travelers and want to share the experience, or pick the private tour if you're traveling as a family or with friends and prefer to keep the day to yourselves: both follow the same route and include the same guide, winery and lunch.

Traveler reviews

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Top questions

What languages is the guide in?

Live guide in English and Italian.

Can children come?

Yes. Ticket types: Child (2 to 9 years); Infant (under 2): free.

Can I do this tour with just my family, or does it have to be a group?

You can choose between a small group tour with up to 12 people or a private tour option for your group alone. Both include the same stops and the same guide service, so the choice depends on whether you prefer to travel with others or keep it to yourselves.

What exactly happens at the winery? Is it just tasting, or do we eat there too?

The winery visit includes both Chianti wine tasting and a light Tuscan lunch served in a relaxed atmosphere, so the food and wine happen together as part of the same experience.

How much walking is involved in San Gimignano?

You'll walk through the medieval town on foot to see the towers and streets, but the operator notes the tour is suitable for all physical fitness levels, and you set your own pace through the village.