These two medieval towns are unrivaled in their preservation of the Tuscan history and culture and are classic stop offs on any Tuscan Experience. Our private driver will prime you with the highlights of each town, leaving you free to explore on your own or with an optional art historical guide.

From: $520.00

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Take a step back in time as you discover the heart of Tuscany

Departing from Florence or surrounds to Siena, the approximately 1-hour drive offers spectacular Tuscan countryside views.

Upon arrival, guests will have 2-3 hours of free time to wander the undulating streets of Siena.

Stepping into the spectacular shell-shaped Piazza del Campo is simply memorizing. Overlooked by the stately Torre del Mangia, it is an experience in itself to enjoy an exquisite espresso or cappuccino in one of the historic cafés lining the square. Time may be spent shopping, exploring the unique artisan stores, visiting the historic churches, from quaint family chapels to the imposing Cathedral that stands sentinel over the city.

The drive from Siena to San Gimignano then takes around half-an-hour, each curve presenting postcard-perfect panorama. Upon request, it is possible to stop along the way for a wine tasting at a Tuscan winery or a traditional lunch. Otherwise, there are great places to dine in Siena or San Gimignano and we would be happy to provide suggestions.

Peppered with soaring medieval towers, the first glimpse of San Gimignano on the horizon is a sight to behold. Within its medieval walls, it has retained much of its ancient charm.

What is it that makes Siena and San Gimignano so extraordinary?

There is the natural beauty of the splendid surrounds, the marvel of the medieval cities, the fascinating history the ancient walls hold within. Then there are the gastronomical delights, from suburb extra-virgin olive oil and incredible wines, cheeses and cured meats, to the sensational recipes from mouth-watering savory delights to delectable desserts.

San Gimignano is also home to one of Tuscany’s – and Italy’s – most beloved white wines, Vernaccia. But there is something more; something magical about this area that is greater than the sum of all its parts. The objective of this private Tuscany tour is to experience this first hand.

Walking up and up the single main street of San Gimignano eventually leads to a lookout offering a vista like no other. For the more history-inclined, there are several churches and museums to visit in Siena and San Gimignano, including the Siena Cathedral with it paved floor encompassing 1000 years of history and the Collegiate Church of San Gimignano which houses the relics of Saint Fina.

Both Siena and San Gimignano are known for their hand-painted ceramics, hand-carved wooden items and leather goods. Aside from the bevy of artisan stores, there are many street artists and studios where you may meet the artists directly. Upon request, an Authorized Tour Guide may be arranged to provide great insight into the villages and their unique histories.


  • Explore two of the most stunning village towns in Tuscany.
  • Enjoy a true immersion into the Tuscan countryside.
  • Stop for a wine tasting at a Tuscan winery along the way if you wish.
  • Lunch suggestions either at a winery estate, or a countryside restaurant in either Siena or San Gimignano.
  • Have your driver meet either at your accommodation in Florence or other convenient location in the morning between 9.00 am and 9.30 am (to be coordinated prior). Tour Length 8 hours.

So that this tour may be tailored to individual preferences, all food and wine tastings are additional, to be paid by guests directly on the day. This ensures our guests may experience the best of the region exactly as they wish. Tasting costs range from approximately € 20-25 (approximately $ USD 25-30) per person, depending on location and tasting options.