Chianti is the most famous region of Tuscany. Filled with rolling hills, beautiful vineyards, picturesque olive groves and ancient castles, it represents the picture-perfect Tuscan ideal. When you go walking in Italy, this is one of the places that you really can’t miss. But although you may have already made up your mind to visit Chianti, which towns should you make an extra effort to see? Here are four places that are certainly worth a visit.

Gaiole in Chianti

Gaiole in Chianti is surrounded by large estates filled with vineyards, so it’s no surprise that some of the best wine in the country comes from this area. This is an idyllic location to visit when you are walking in Italy, and is situated about 40 kilometres from Florence along the valley of the River Massellone.

It is famous for its attractive monuments, including the Abbey of Coltibuono and the 11th century Castle of Brolio, so if you want to visit some historical sites whilst walking in Italy, you’ll find plenty here.

Greve in Chianti

When you go walking in Italy you are sure to see many fabulous places, and Greve in Chianti is one of them. This is the most important town in the region, largely as a result of its weekly market that is held in the attractive central Piazza. It is also the setting for an annual wine convention.

Filled with beautiful buildings, there is plenty to see as you stroll around the town. Although you’ll find lots of tourists sharing the space with you, it’s still a delightful and very attractive place to visit whilst walking in Italy.

Radda in Chianti

The fascinating mediaeval centre of Radda in Chianti is a good enough reason to stop by here when you are walking in Italy. Packed full of tiny lanes and grand archways, this is an incredibly attractive location that is hugely popular with visitors to the region. Surrounded by vineyards, castles and beautiful countryside, it makes for a perfect place to visit during your holiday.

Castellina in Chianti

Arguably the main attraction in Castellina in Chianti is the Rocca Comunale, a large 15th century fortress that has now been converted into the town hall. But it’s not the only historically-significant building you’ll find here if you pass through whilst walking in Italy: you’ll also be able to visit the Church of San Salvatore, a 16th-century building containing a fresco of the Madonna. There are some excellent views to be had from the fortress, and the town also includes a large piazza and some great restaurants to stop off in during your trip.

Go Exploring

Of course, there are plenty of other beautiful towns to explore in Chianti, but these are a great start if you are heading to Tuscany on a walking holiday. You can even walk from town to town throughout the region because the settlements are not spread too far apart. Each has its own unique charm and points of interest, so try to visit as many as possible next time you are walking in Italy.