Explore Tuscany’s medieval gems with a private Chianti tour, savoring authentic flavors and fine wines. Book your unforgettable journey today.
Explore Tuscany’s medieval gems with a private Chianti tour, savoring authentic flavors and fine wines. Book your unforgettable journey today.
- Siena - Siena – First stop of the tour: where time has stopped Dive into a timeless setting, where each stone narrates tales of the Middle Ages, art, passion, and the city’s pride. Nestled in the picturesque Tuscan hills, Siena is a true treasure trove of beauty that captivates at first sight. This city, a UNESCO World Heritage Site, maintains…
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Siena - Siena – First stop of the tour: where time has stopped Dive into a timeless setting, where each stone narrates tales of the Middle Ages, art, passion, and the city’s pride. Nestled in the picturesque Tuscan hills, Siena is a true treasure trove of beauty that captivates at first sight. This city, a UNESCO World Heritage Site, maintains its ancient allure: steep streets, brick buildings, Gothic arches, and stunning views that suddenly appear through tranquil alleys. Every corner radiates the serenity and pride of a city that was once a powerful independent republic, in perpetual rivalry with Florence. Siena is renowned for its Palio, but it offers much more: it embodies gothic spirituality in its black and white Duomo, showcases art in the works of Simone Martini and Ambrogio Lorenzetti, and offers authentic taste in the flavors of Tuscan cuisine, from pici to ragout to spiced panforte. It is the ideal starting point for a journey that seeks to touch the soul of Italy.
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Castello Monteriggioni - *Second stage: The Castle of Monteriggioni –
This small fortified village is a perfectly preserved medieval gem, renowned for its impressive city walls that still encircle the town like a crown of towers, just as Dante described it in the Divine Comedy. The walls, constructed in the thirteenth century by the Sienese to protect the northern border against Florence, feature 14 crenellated towers that overlook the countryside below. Strolling along the walkway offers breathtaking views of the Tuscan landscape and a plunge into the most genuine history. Inside, life moves slowly through the cobbled streets, the piazza Roma with its Romanesque church, small craft shops, and places to enjoy a glass of Chianti. Monteriggioni may be small, but it enchants with its preserved atmosphere, suspended between reality and legend.
- San Gimignano - Third stage: San Gimignano – Medieval Manhattan
As you approach San Gimignano, the landscape transforms once more: on the verdant hills of the Tuscan scenery, the soaring towers that have made this village famous worldwide rise towards the sky. An ancient symbol of power and prestige, the towers of San Gimignano resemble stone fingers pointing to the sky, narrating the story of a prosperous and ambitious city in the heart of the Middle Ages.
The heart of the village is the Piazza della Cisterna, paved with herringbone, surrounded by historic buildings and dominated by the Devil’s Tower. A little further on, the Piazza del Duomo, with the Collegiate Church and the Palazzo Comunale, houses frescoes by the Sienese school and offers a spectacular view from the Torre Grossa, the tallest tower in the city.

- Private transportation
- Booster seat
- Bottled water
- On-board WiFi
- Alcoholic beverages
- Lunch
- In-vehicle air conditioning
- Private transportation
- Booster seat
- Bottled water
- On-board WiFi
- Alcoholic beverages
- Lunch
- In-vehicle air conditioning
- Dinner
- Dinner
Allow yourself to be led through the medieval wonders of Siena, the iconic towers of San Gimignano, and the ageless charm of Monteriggioni.
In the heart of Chianti, enjoy a pause amidst ancient vineyards with a traditional Tuscan lunch and exquisite wine tasting.
This exclusive tour, in a private car with all amenities, is perfect for those in search…
Allow yourself to be led through the medieval wonders of Siena, the iconic towers of San Gimignano, and the ageless charm of Monteriggioni.
In the heart of Chianti, enjoy a pause amidst ancient vineyards with a traditional Tuscan lunch and exquisite wine tasting.
This exclusive tour, in a private car with all amenities, is perfect for those in search of genuine emotions, distinctive flavors, and endless beauty.
An experience rich in history, nature, and fine wine. Reserve your journey in the heart of Tuscany today!
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.