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Siena and San Gimignano Tour with Winery Lunch and Private Guide

Private guided Siena, winery lunch & San Gimignano stroll

Enjoy an immersive Siena and San Gimignano tour designed for travelers seeking both history and flavor.

Guided by your private English-speaking guide ( 2 hours ), begin with Siena’s medieval streets, Renaissance palaces, and the magnificent Duomo.

Pause for a Tuscan lunch with wine pairings in a boutique Chianti Classico winery before continuing to the towers of San Gimignano, where artisan shops and the world’s best gelato await.

This full-day experience blends Tuscany’s culture, landscapes, and cuisine in one unforgettable journey.

Tour Highlights what makes this tour unique

  • Private Guided Tour of Siena ( 2 hours ): Explore medieval streets, Piazza del Campo, and the stunning Duomo.
  • Lunch in a Chianti Winery: Taste Tuscan cuisine and Chianti Classico wines in an authentic wine estate.
  • San Gimignano Afternoon Stroll: Wander the UNESCO hilltop town, admire its towers, and enjoy artisanal gelato.

 

Tour Overview a classy touch

  • Pick-up and Drop-off at your accommodation (quoted separately)
  • Private group experience for a tailored, exclusive journey
  • English-speaking Driver Guide at your disposal for the day
  • Guided walking tour of Siena’s historic center and landmarks
  • Lunch with wine pairings in a Chianti Classico winery
  • Free time in San Gimignano for shopping, gelato, and exploration

about us

a kind of family business…

Over 15 years of experience in wine, gastronomy, and bespoke travel design.

Niccolò is our wine and tour expert, with deep knowledge of Tuscany’s terroirs and producers, curating experiences defined by refined access and local insight.

Alexandra, a top-rated chef, personally leads and oversees our cooking experiences, ensuring professional standards, storytelling, and authentic Tuscan cuisine throughout.

We are supported by a dedicated team of experienced travel designers and trusted driver-guides, allowing us to deliver seamless execution, discretion, and the level of service expected by luxury travelers and their advisors.

Your Questions Answered

The Siena and San Gimignano Tour is a full-day guided experience exploring two iconic Tuscan destinations, combining the medieval streets of Siena with the towered skyline of San Gimignano, enriched by cultural insights and local flavors.

In Siena, you’ll visit Piazza del Campo, the historic center, and scenic viewpoints, learning about the city’s art, history, and traditions from your guide.

In San Gimignano, you’ll explore the medieval towers, charming squares, and artisan shops, with time to enjoy the local atmosphere and panoramic views of the Tuscan countryside.

Yes, the tour typically includes a traditional Tuscan lunch at a selected restaurant featuring regional specialties.

Yes, dietary requirements such as vegetarian, gluten-free, or food allergies can be accommodated upon request. Please inform us in advance so meals and tastings can be tailored to your needs.

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Siena and San Gimignano Tour with Winery Lunch and Private Guide

Starting from

€ 320

Starting from
€ 320
Siena and San Gimignano Tour with Winery Lunch and Private Guide
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