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Discover the Most Stunning Hilltop Towns on a Chianti Tour from Florence by Laura Jeeves

Discover the Most Stunning Hilltop Towns on a Chianti Tour from Florence by
Article Posted: 08/24/2020
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Discover the Most Stunning Hilltop Towns on a Chianti Tour from Florence

Travel & Tourism
Tuscany is famed for its architecture, natural beauty and delicious food – but most of all, it is known for its medieval hilltop towns. These picturesque villages are not to be missed, even if you only have a handful of days in the region.

That’s why we’ve put together a list of the most beautiful hilltop towns to visit on a Chianti tour from Florence. A visit to any one of these top destinations promises fascinating history, fabulous views, and fantastic fortifications.

San Gimignano

Back in the Middle Ages, pilgrims would stop off at San Gimignano during their journey to Rome. Today, the town is marvellously well preserved despite being a flourishing tourist destination.

Known as the ‘Manhattan’ of Tuscany, San Gimignano is known worldwide for its medieval towers. Doubling as both a display of military and financial power, the fourteen remaining constructions are truly a medieval marvel not to be missed.

Radda in Chianti

If sampling local wine and ambling along labyrinthine streets and ancient defensive walls sounds like the perfect day out to you, then make sure you visit Radda on a Chianti tour from Florence. This charming hilltop village promises panoramic views over vineyards and rolling countryside. Venture into the Palazzo del Podestà and Church of S. Niccolo for a taste of local history and culture before delving into the wine cellars.


This Etruscan gem lies off the beaten path. Situated between the Cecina and Dell’Era valleys and famed for its connection to the Twilight film franchise, Volterra is sure to be an interesting stop on a Chianti tour from Florence.

You will quickly fall in love with the reddish hues of the buildings as you make your way to the heart and centre of the town, Piazza dei Priori. Once there, you will be able to explore the Palazzo dei Priori and Palazzo Pretorio, as well as the Tower of the Little Pig, for a healthy dose of Volterra’s history.


Overlooking the beautiful Crete Senesi area in Val d’Orcia, you will discover the hill town Montalcino. This well-preserved thirteenth century paradise should be high on the agenda for wine lovers looking to go on a Chianti tour from Florence. There are plenty of wineries to stop off in after exploring the castle and its surrounding olive groves.


Dating back to the Etruscans, Castellina boasts an impressive military past. It operated as a strategic headquarters between Siena and Florence, and to this day you can see this important historical heritage in both the towering Rocca castle and the Via delle Volte underground roads.

The aristocracy also owned many properties in Castellina at that time, some of which are still standing. Those interested in the older history of the town will likewise enjoy a visit to the Etruscan tombs of Montecalvario.

These are just some of the many incredible hilltop towns to enjoy on a Chianti tour from Florence. To get the most out of your experience, book a day trip with a local tour operator; having a guide accompany you will bring the place to life and make your time there even more unforgettable.

Author Plate

Mauro Bramante is the Director of WalkAbout Florence, an independent business offering unforgettable tours and excursions around Italy including the best Chianti tour from Florence. Whether you want to ride a Vintage Vespa, try the famous Chianti wine or get cooking with fresh local ingredients, Mauro's company promises excitement, adventure and above all, fun. If you're keen to experience the magic of Italy with the help of some passionate and knowledgeable tour guides, look no further than WalkAbout Florence for your next getaway.

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