Self Guided Walking Tours in Tuscany

The terrain of the San Palo Ring walk includes a range of valleys, ridges and deserted farmhouses with a good spot for a lunch break in the tiny hamlet of Poggio San Palo. Grades are gentle with the occasional challenge. The walk provides an opportunity to enjoy the traditional Tuscan landscape and a glimpse of rural life as it has been for the past millennium. Excellent examples along pathways of dry stonewalls leading to centuries old terraces, long since cleared in most other parts of Chianti. The Pieve of San Giusto provides a welcome break as it did more than 1000 years prior for travellers.

Your destination is clearly visible from Radda as you head towards the beautiful fortified Hilltown of Volpaia. This ring walk takes you past classic Chianti vineyards, olive groves, an 11C Fattoria, a 10C Pieve, one standing high with wonderful views back to Radda and the other nestled into a peaceful setting surrounded by ancient olive trees.

Castello di Volpaia our mid point for the walk stands in a splendid panoramic position (617m). Wine and olive oil has been produced here since the 11C. Today, the wine and oil production is housed throughout the village buildings and churches.

You can book ahead for a very interesting tour of the wine cellars and olive oil processing plant finishing in a beautiful old building sampling Volpaia wine and olive oil. Just as enjoyable is having lunch at a cafe in Volpaia's small piazza. Look for our recommendations in the Walkers Pack for both restaurants and the delightful locals you will meet.

This pleasant walk links Radda and Castellina, two of the three Chianti League Hilltowns.

After a 10-minute bus ride from Radda to Castellina, our walk meanders though woods, isolated farmhouses and also has some of the best expansive views in the area. Allow time to explore Castellina, a Hilltown that holds an important place in history.

Castellina started as a trading town in Etruscan times and was on the front line of the wars continually taking place between Florence and Sienna. There is still much to see including an Etruscan tomb, a well-restored castle housing an Etruscan museum and an impressive vault to explore.

The walk starts in Lamole sited at 600 meters, after a bus ride offering the most panoramic views. The path winds steadily though beautiful ancient chestnut forests, past stonewalls, small village gardens, and deserted farmhouses. The mountains of the Apennines can often be seen in the distance. For a reasonably isolated area there are surprising opportunities to stop for coffee or lunch along the way before returning to Radda.

A ring walk from Radda to Gaiole an important market town in past times due to its position on the cross roads between the Chianti district and the upper Arno valley. Our walk winds through olives groves and shaded woods, past a 16C baroque villa and though a delightfully preserved hamlet with a tower.

Allow time to explore Gaiole, the third town that made up the Chianti League in the 13C. Perhaps enjoy lunch or coffee in Gaiole's main pedestrian street and piazza.

A gentle, shorter option if your day calls for this. The walk provides views back to Radda not seen from any other walk and explores a ridge lined with Holm oaks and juniper bushes. It passes an old lookout tower with a return via La Villa.