San Gimignano, Chianti & Montalcino day trip from Siena

Medieval streets, vineyard views, and seven wines in one day

A full-day tour from Siena visits San Gimignano, Chianti and Montalcino in a small air-conditioned group, with stops at two wine estates for tastings, a Tuscan lunch, and samples of olive oil and balsamic vinegar. You walk the medieval streets of each town during free time, tour the wineries with a guide, and taste seven wines across the day.

Step-by-step itinerary

Explore San Gimignano and Montalcino

• Meet staff at Siena Station
• Travel by minivan
• Free time in San Gimignano
• Optional visit to Cathedral of San Gimignano
• Lunch and wine tasting in Montalcino winery
• Free time in Montalcino

The experience

The day starts at Siena Railway Station, where you meet the staff in green shirts and board an air-conditioned minivan or minibus. The route takes you through the Chianti region to San Gimignano first, where you have free time to wander the medieval streets and, if you choose, visit the Cathedral. The town sits on a hilltop with narrow lanes and stone towers that rise above the surrounding vineyards.

Lunch and wine tasting happen at a local winery in Montalcino, where you taste Brunello di Montalcino and sample local olive oil and balsamic vinegar. You then have free time in Montalcino to explore the town and the Montalcino Fortress. The tour includes visits to two wine estates (one of them exclusive to this group) with seven wines tasted in total across the day. A multilingual guide provides commentary in English, Spanish or Italian, with translation support during tastings when needed.

The full day runs about eleven hours from start to finish. A moderate amount of stairs and walking is involved, particularly in the medieval towns and at the fortress. Vegetarian options are available for lunch if you note any dietary requirements when booking. The itinerary may shift slightly, but all three towns and both wine estates remain part of the day.

What’s included

• Expert multilingual guide.
• lunch at a local winery in Montalcino.
• tastings of seven wines across two estates, one exclusive to the tour.
• samples of olive oil and balsamic vinegar.
• air-conditioned transport in a small group vehicle.
• all entrance fees and winery visits.

Before you book

Days and timesMonday, Thursday and SundayDeparts at 08:30

Book up toStart time

AgesAdult (13 and older) · Child (3 to 12 years) · Infant (under 3): free

GroupUp to 29 · max 8 per booking

Live guideEnglish, Spanish 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 yesterday

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by myTour in Italy

Is this one for you?The guide speaks English, Spanish or Italian with translation support during tastings, so you follow comfortably even if your language skills are limited. The group stays small (up to eight in a minivan or up to thirty in a minibus), which keeps the pace manageable for anyone comfortable with moderate walking and stairs.

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Top questions

What languages is the tour guided in?

Live guide in English, Spanish and Italian.

Can children come?

Yes. Ticket types: Child (3 to 12 years); Infant (under 3): free.

What is the Cathedral of San Gimignano and can I visit it during the tour?

The Cathedral of San Gimignano is a medieval church in the town center. It's optional during your free time there. You can visit it if you choose, or spend the time exploring the streets and piazzas instead.

How many wine tastings are included and where do they happen?

Seven wines are tasted across the day at two wine estates, one of which is exclusive to this tour group. Lunch and tasting take place at a local winery in Montalcino, and the second estate is visited separately with additional tastings.

What samples of local food and drink are included besides the wine?

Olive oil and balsamic vinegar sampling are included, along with a Tuscan lunch at the winery in Montalcino. Vegetarian options are available if you request them at booking.

How much free time do I have to explore each town on my own?

You have free time in San Gimignano to walk the medieval streets and visit sites like the Cathedral if you wish, and free time in Montalcino after lunch to explore the town and the Montalcino Fortress before the return journey to Siena.

What is the physical demand of this tour?

A moderate amount of stairs and walking is involved, particularly navigating the medieval towns and climbing to the Montalcino Fortress. You must be able to climb and descend stairs comfortably.