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  • Siena & San Gimignano with Tuscan Dinner

Embark on a journey of discovery across Tuscany,  to experience the charm of Siena, San Gimignano, and the Chianti countryside. Delight in the character of ancient cities, medieval towers, and a sunset casting its warm glow over the hills of Tuscany, culminating in a sensory adventure with wine tasting and an authentic Tuscan dinner.


  • Visit the historical marvels of Siena and its surroundings
  • Free time to explore the unforgettable Medieval Towers of San Gimignano
  • Seasonal culinary delights in Chianti countryside


Embark on an enchanting journey through the heart of Tuscany, a region steeped in history, culture, and culinary delights. Our carefully crafted tour invites you to uncover the timeless allure of Siena, San Gimignano, and the captivating Chianti countryside, creating memories that will linger like the rich flavors of Tuscan wine.

As you depart from Florence, a luxurious air-conditioned mini-van,  and eloquent English-speaking driver-guide become your portal to the treasures of Tuscany. Let Siena, a city that once rivaled Florence in power, indulgence, and artistic splendor, unfolds before you. Traverse the narrow streets and relive the history of the 17 medieval city communities, known as Contrade, which passionately compete in the annual Palio horse race. The grandeur of Piazza del Campo, the central square where this thrilling event transpires, will captivate your senses.

But the journey doesn’t end there; next up is San Gimignano, a town renowned for its medieval towers that pierce the sky, creating a silhouette. Wander through the labyrinth of high walls and narrow streets, absorbing the unique atmosphere of this Tuscan hill town. Marvel at the dozen tower houses that stand as sentinels, preserving a bygone era against the backdrop of the hilltop and its protective walls.

As the day unfolds, witness the sun gracefully setting over the undulating Tuscan hills, casting a warm glow on the landscape. Then, indulge in a sensorial experience, as you partake in a wine tasting amid the picturesque Chianti countryside. Discover the ancient cellars that cradle the essence of Tuscan winemaking, unraveling the intricacies of each sip.

The crescendo of your adventure is a typical Tuscan dinner, a symphony of flavors that dance on your palate. Succulent dishes steeped in tradition, crafted with passion, and served in a captivating locale, offer a gastronomic journey through the heart of Tuscany.

This meticulously curated experience provides a comprehensive exploration of the Tuscan countryside, encompassing the cultural gems of Siena and San Gimignano, and culminating in the indulgence of top-notch Tuscan food and wine.


  • Transportation to & from Florence by luxury Mercedes van
  • English speaking driver and guide
  • Guided walking tour of Siena with professional English speaking guide
  • Surprise tasting in Siena
  • San Gimignano visit with free time
  • Typical Tuscan dinner
  • Guided visit of a winery with wine tasting


  • Hotel pickup and drop-off
  • Gratuities

Know before you book

  • Due to the route covered and/or the means of transportation used, it is not possible to participate in this tour using a wheelchair, scooter, or other aid. Please contact us to inquire about customized tour options for guests with mobility challenges
  • Children under 18 must be accompanied by an adult
  • Max 20 participants per tour

Know before you go

  • Dress code: shoulders and knees must be covered
  • Tour departs rain or shine

Cancellation Policy

  • Tours depart rain or shine unless otherwise specified.
  • All cancellations must be received in writing. Tours and passes will be refunded if cancelled more than 48 hours before the tour start time.
  • No refunds will be made for cancellations with less than 48 hours notice or failure to arrive at the meeting point on time (no-show).

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