San Gimignano & Chianti Day Trip Small Group Tour

Medieval towers, Chianti vineyards, and award-winning gelato in one unhurried day

A small-group day trip from Montecatini through Chianti villages to San Gimignano, traveling by private Mercedes minivan with an English-speaking driver-guide. The route takes in a market town known for wild boar and pecorino, a medieval hamlet where Amerigo Vespucci was born, a Tuscan abbey set among Antinori vineyards, and the hilltop town of San Gimignano with its white Vernaccia wine and saffron heritage. Hotel pickup and drop-off are included.

Step-by-step itinerary

Chianti countryside and San Gimignano tour

• Visit charming market town
• Pass by Amerigo Vespucci's birthplace
• Relax at abbey and vineyards
• Enjoy typical Tuscan lunch
• Stroll medieval San Gimignano
• Explore cobbled streets and piazzas
• Visit Gelateria di Piazza

The experience

San Gimignano sits on a hilltop in central Tuscany, ringed by medieval towers and cobbled streets that have barely changed in centuries. The day starts with pickup from your Montecatini hotel, then heads into the Chianti countryside in a comfortable minivan that holds up to seven people. The route unfolds through villages most travelers miss: a market town where Antica Macelleria Falorni has been curing wild boar and aging pecorino for generations, and a smaller hamlet that was the birthplace of Amerigo Vespucci, the explorer America is named after.

Midday brings you to an abbey set directly into the Antinori vineyards, where you have time to sit, take in the rolling landscape, and eat a typical Tuscan lunch (you arrange and pay for this separately). The afternoon is reserved for San Gimignano itself: a stroll through the tower-topped town on foot, with time to wander the piazzas and narrow streets at your own pace. The town is famous for Vernaccia di San Gimignano, a crisp white wine, and for saffron, which was cultivated here in the Middle Ages and is being farmed again. Gelateria di Piazza, run by award-winning gelato maker Sergio Dondoli, sits in the main square. His Vernaccia wine sorbet is one of his signature flavors.

The driver-guide speaks English and Italian, and the day is built around a leisurely pace rather than a checklist. Bottled water is provided during the drive. Hotel drop-off happens at the end of the afternoon, completing a nine-hour outing that stays within the Tuscan countryside without requiring a rental car or navigation on your own.

What’s included

• Montecatini hotel, villa or apartment pickup and drop-off.
• bottled water during the drive.
• private minivan transport.
• English and Italian-speaking driver-guide for the full day.

Before you book

Days and timesEvery dayDeparts at 09:00

GroupPrivate

Live guideEnglish and Italian

Meeting point and pickupHotel pickup included.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated yesterday

Good to know

Low physical effortStroller-friendlyInfant seats availablePets welcome

Operated by Luccalimo

Is this one for you?Hotel pickup from Montecatini means you don't need a rental car or the stress of navigating Tuscan roads yourself. The driver handles the route while you settle into the countryside. The small group size keeps the minivan intimate and allows the guide to tailor the pace to what interests the people on board.

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Top questions

What languages is the tour guided in?

Live guide in English and Italian.

What is San Gimignano known for?

San Gimignano is a medieval hilltop town with towers that dominate its skyline and cobbled streets that form a UNESCO World Heritage site. It is renowned for Vernaccia di San Gimignano, a white wine produced locally, and for saffron farming, which was an important part of the city's medieval economy and has been revived in recent years.

Do we stop to taste wine on this tour?

Wine tastings are not included in the tour price. You pass through Chianti wine country and visit an abbey set among Antinori vineyards where you have time to relax, but any wine purchases or tastings are arranged and paid for separately during your time there.

Where does the day start and how do we travel?

The day begins with pickup from your hotel, villa or apartment in Montecatini. You travel in a private Mercedes minivan with an English-speaking driver-guide, which holds up to seven passengers and allows the group to move together through the countryside without needing individual cars or navigation.

What is included in the price?

Hotel pickup and drop-off in Montecatini, transport by private minivan, a driver-guide who speaks English and Italian, and bottled water during the drive are all included. Lunch, wine tastings, museum or monument entry fees, and gratuities are not included and are arranged separately.

How much time do we spend in San Gimignano?

The afternoon is reserved for San Gimignano, with time to explore the medieval town on foot, walk the cobbled streets and piazzas, and visit sites like Gelateria di Piazza at your own pace. The exact duration depends on the group's interests, but it is unhurried rather than rushed.