In focus: Tuscany’s Chianti Region

The Chianti region is well known for being the wine-producing heart of Tuscany and if you’re looking for a European walking holiday that allows you to indulge in fine dining and excellent tipples, there are few better places to travel to.

We’re going to take a look at what you can see as you explore Chianti, with a particular focus on the outstanding wines produced in the Chianti Classico region, which you should allow at least a day to discover.

If all of this piques your interest in trekking in Italy, check out some of the itineraries available here for inspiration for your next holiday.

San Gimignano

As you wander through the rolling hills and valleys of Tuscany you’ll often catch a glimpse of the intriguing-looking towers of San Gimignano. This medieval town sits atop a hill and is a real delight to explore.

The towers that make it so recognisable have an interesting story behind them – they were constructed by the town’s wealthy families as a mark of their power and financial standing. Although 13 still remain, in the 14th century there were 72 of these landmarks dotted throughout San Gimignano.

You can also begin your discovery of Tuscany’s wines here by paying a visit to the Vernaccia Wine Museum, where you can learn about the vintages produced in San Gimignano and taste some of the tipples.

Photo Credit: "View of San Gimignano Tuscany" by Frank Kovalchek on Flickr

Photo Credit: “View of San Gimignano Tuscany” by Frank Kovalchek on Flickr


Although it may be tempting to spend your entire trip wandering in Tuscany’s rolling hills and stunning countryside, you should really spend time in at least one of its big cities. Siena marks one side of the Chianti region and is a real gem.

It has wonderful Gothic buildings within its centre – which is free of traffic – making it a lovely place to walk around. In its main square – Piazza del Campo – you’ll find its impressive 100 m high bell tower and the beautiful Palazzo Pubblico.

Chianti Classico

The Chianti Classico region is nestled between Florence and Siena and is one of the oldest areas of vineyards in Tuscany. The wines that fall under the Chianti Classico label are varied, but must meet strict criteria – for instance, they all need to contain at least 80 per cent sangiovese grapes, the typical red variety grown here.

Walking in this area is a real delight, as you’ll have rows and rows of grapevines stretching out in front of you, as well as fields of colourful flowers, while elsewhere you’ll encounter sections of shady pine forests. Of course, you should plan plenty of stops on your hike to allow you to explore the vineyards properly.

The following are a couple of the wineries you may want to pop into.

Photo Credit: "Siena, Tuscany" by Phillip Capper on Flickr

Photo Credit: “Siena, Tuscany” by Phillip Capper on Flickr

Villa Pomona

You’ll find Villa Pomona in Castellina, where it’s run by Monica Raspi. She took on her family vineyard when her mother told her she was planning to sell it and has been making her own blend of Chianti Classico ever since.

As well as the grapes, Villa Pomona also boasts olive groves – you can take a look around the estate before sampling some of its produce.


Just outside the village of Panzano is the Fontodi estate, which has 80 hectares of vines, as well as an extensive olive grove. Enjoy the Tuscan hospitality when you visit here, with owner Giovanni Manetti happy to supply samples to travellers without any obligation to buy a bottle.

The whole vineyard is organic and a real treat to explore – between the rows of vines are barley plants, which aid the cultivation of the grapes and provide food for the herd of Chianina cattle that live on the farm.

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