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The Republic of Siena built the fortified village of Monteriggioni between 1214-1219 to help protect itself against rival Florence.

Florence tried to take over Monteriggioni in battles in 1244 and 1254 and again in 1269 after the ‘Battle of the Hill’ saw the Sienese flee to Monteriggioni.

Battles continued over Monteriggini throughout the 1300-1500s, until Florence finally won possession of Siena and thus Monteriggioni.

The locals were bought to Florence as slaves by Cosimo de’ Medici I. The Medici later sold Monteriggioni, before it was sold again to the Griccioli family that own Monteriggioni to this day.

With a diameter of just 172 metres, Monteriggioni is surrounded by walls that are 2-metres thick, with two gates that would have been closed to serve as further protection against attack. Today the gate structure remains but all that remains of the doors themselves are the hooks that once held them in place.

There were once 15 towers built into the surrounding walls that reached heights of 6.5 metres, although today only 11 remain at this height.

Outside the walls, there was once a moat-type ring that would have been filed with coal. Whenever Monteriggioni came under attack, this combustible material would have been lit to form a defensive ring of fire around the Tuscan village.

Further beyond the walls, orchards and gardens would have not only sustained those posted in Monteriggioni but also served as an added defence.

Central to Monteriggioni is the Piazza Roma. Here there is also the Church of Santa Maria Assunta. Today, there are also several coffee shops and eateries, wine stores, craft stores and more, with the income of Monteriggioni now reliant on tourism more than the traditional pastoral and agricultural trades.

The Best of Tuscany Tour - Enjoy a Small Group Tour!

The Best of Tuscany Tour - Enjoy a Small Group Tour!

A small group, three splendid Tuscan towns, extraordinary guides, and lunch & wine tasting at a Tuscan estate!

Countryside - Food - € 189.00

The original Best of Tuscany tour with a small group-Savour the sights, smells and tastes of the region on this visit to three captivating hilltop towns. Our small-group expeditions, led by fabulous local guides, also offer a delicious lunch and wine tasting at a traditional estate.

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Exclusive Best of Tuscany Tour-Your Own Private Tuscany Tour

Exclusive Best of Tuscany Tour-Your Own Private Tuscany Tour

Your own special Tuscan day of beauty, exploration, and delicious dining in the countryside.

Active & Outdoors - from € 200.00

Your own private guide and transport to experience the beauty and authenticity of Italy’s most beloved region-Tuscany. Enjoy a full-day’s exploration of this stunning landscape during a visit that is professionally tailored for you.  Take in breathtaking views complete with the tapestry of vineyards and shimmering olive groves. This truly authentic experience will lead you through amazing medieval hilltop towns (Tuscany's most famous) to explore the beautiful frescoes that adorn the walls of many of the local churches. Afterwards, sample some regional wines during lunch at one of the nearby traditional Tuscan estates. 

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