Tuscany: A Vespa Journey from San Gimignano through the Chianti Countryside – Wine Tasting & Tuscan Lunch

You’ll set out from the medieval heart of San Gimignano and spend the day discovering the Chianti countryside from the seat of a Vespa. Quiet country roads lead you between vineyards, olive groves and panoramic hilltop landscapes before the experience slows down at a local winery for a vineyard visit, Tuscan lunch and guided tasting of wine, extra virgin olive oil and balsamic vinegar.

The Experience

From San Gimignano into the Hills

Your journey begins at Porta San Matteo in the historic centre of San Gimignano. After a short introduction and driving lesson, you leave the town behind and follow your guide along scenic roads through the Chianti countryside.

The route winds between vineyards and olive groves, with stops at carefully chosen viewpoints for photographs and time to take in the landscape. Along the way, you’ll also discover more about the history, culture and winemaking traditions of this part of Tuscany.

The Medieval Heart of San Gimignano

Part of the experience brings you back to San Gimignano, known for the medieval towers that rise above its historic centre. You’ll explore the town with your guide, take in its views and pause for a taste of its famous Dondoli gelato before continuing the journey.

From Vineyard to Tuscan Table

Later, you arrive at a local winery for a visit through the vineyard and estate. The day continues around the table with a traditional light Tuscan lunch accompanied by a guided wine tasting, alongside locally produced extra virgin olive oil and balsamic vinegar.

There is also time to discover local products from the estate, with the possibility to purchase and ship them home.

What Awaits

• Around five to six hours between San Gimignano and the Chianti countryside
• A guided Vespa ride along scenic Tuscan roads
• Helmets, insurance and secure lockers included
• A guided visit through historic San Gimignano
• A vineyard and winery visit
• Tuscan light lunch with wine, olive oil and balsamic vinegar tasting
• Experiences available in English, Italian and Spanish

Beyond the Experience

You can drive your own Vespa or share one with someone else. Drivers must be at least 18 and bring their original valid driving licence, while passengers do not need a licence. If you prefer not to drive, you can ride with one of the guides instead.

Vegetarian, vegan and gluten-free lunches can also be arranged on request. Long trousers and closed shoes are recommended for the ride.

An Invitation

This is Tuscany experienced with the road open in front of you. You leave the stone streets of San Gimignano behind, ride between vineyards and olive groves and eventually slow down around a table of local wine and Tuscan flavours. A day that brings together the landscape, food and effortless sense of freedom that make travelling through Tuscany feel so distinctive.