Siena Walking Tours

your taste of Tuscany with a local guide

crete landscape roe deer val d orcia wild orchids

rolling hills in Tuscany

elusive roe deer

parish church among old cypress trees

beautiful wild orchids

Country Tours
Guided walks in the countryside near Siena, enjoying the rolling hills of Tuscany, looking at breathtaking views and encountering medieval hamlets.
Costanza walking

Country Tours

The province of Siena is one of the widest of all Tuscany and comprehends many areas, from the lunar landscapes of the Crete (clay hills) to the Chianti vineyards. They are all different and have their specific beauties but all of them have something in common: they are soul-stirring. Let’s take a walk then!

Walking is the best way to observe landscapes, animals tracks and bits of history up close. It is also the most natural and simple physical activity, that everybody can do. You can discover the most evocative places, walk along former roman routes or the Francigena route, like the pilgrims used to do in the Middle Ages. Besides walking, we visit hill-top towns or abbeys rich in history and unique works of art.

The walks range from 4 to 9 miles, keep in mind that this area is beautiful as it has nice hills, so those are also included in the walks! But we can take it easy and burn off our pasta!

leaving Pienza

Pienza to Montepulciano, a Renaissance taste

We meet in Pienza, ideal Renaissance city planned in the 1400’s by the Pope Pius II, today well known also for the pecorino cheese (sheep's milk cheese) that can be tasted in one of the shops along the main street. read more

gate of Monteriggioni

Walking the history

We look for ancient paths on the Francigena route, used by pilgrims since the year 800 a.D. on their way to or from Rome, when going on a pilgrimage was the goal of a lifetime. read more

'uva' grape

Enchanting Chianti

You certainly know well the word Chianti, but to you it probably means just a typical red wine from Tuscany. That is true, but Chianti is much more than that, it is a specific hilly region between Florence and Siena. read more

Sant'Antimo abbey

Montalcino to Sant'Antimo, the singing stone

Montalcino is the headquarter of the excellent Brunello, one of the best red wines in Tuscany. The town is perched on a hill and we can enjoy the beautiful panorama from the top of its medieval fortress. read more


Castelvecchio walk

We plunge into one of the 14 Natural Reserves of Siena province, Castelvecchio, a medieval old Castle, whose fascinating remains are immersed into the vegetation and can be reached only on foot. read more

Monte Oliveto abbey

A walk of art in the Crete

The walk starts from the lovely village of San Giovani d’Asso, known for its white truffles and the first museum in Europe dedicated to this delicacy. read more

Bagno Vignoni

Salus per aquam

Salus per aquam, latin for "health through water", a special water coming from thermal hot springs, that made the tiny village of Bagno Vignoni such an important stop along the via Francigena. read more

Above you find some examples. I can provide itineraries tailored on specific request, to satisfy your needs and curiosity and let you choose with a lot of flexibility, you are on vacation, after all!
For further information, please contact me.