Tuscany is not just art and medieval villages. It is also a territory with a network of trails crossing vineyards, oak forests, open meadows and UNESCO landscapes. Those who love walking find material here for weeks of excursions.
From Poggibonsi, you can easily access very different routes in terms of difficulty, length and landscape.
The Poggibonsi-San Gimignano stretch of the Via Francigena: 12 km of hills, vineyards and olive groves. The arrival point - the medieval towers of San Gimignano on the horizon - is one of the most satisfying of the entire route. Three thousand years of history underfoot.
Trekking in Tuscany: landscapes worth every step
Trekking in Tuscany has different characteristics from mountain trekking. There are no demanding peaks or alpinist elevation gains. Instead there are trails on rolling hills, with 360-degree panoramas, through landscapes that change with every season.
The advantage of Tuscan trekking is accessibility: many routes are easily reached by car, start from villages with parking, and form a loop or point-to-point with bus return options. You do not need to be a mountaineer to enjoy extraordinary days.
Trails in Chianti: through vineyards and olive groves
Chianti is the territory richest in marked trails near Poggibonsi. The CAI (Italian Alpine Club) trail network covers the entire area with well-signed routes.
Castellina in Chianti ring (15 km, about 4-5 hours): a circular route starting from the village, descending into the valleys, crossing vineyards and olive groves, climbing back up to the farmhouses. Moderate elevation change, suitable for everyone.
Pievi Route: follows the itinerary of the ancient Romanesque parish churches of Chianti - San Pietro in Bossolo, Pieve di Cellole, Pieve di Corbaia - connecting them with forest paths. A way to combine trekking and history.
Chianti white roads: many unpaved roads in Chianti are walkable as well as cyclable. They are less suited to trail hiking but offer linear routes with simple signposting.
The Via Francigena on foot: the Val d’Elsa stretch
The Via Francigena - the medieval pilgrimage route from Canterbury to Rome - crosses the Val d’Elsa and passes through Poggibonsi. Walking even just a stretch of this route is a different experience from conventional trekking: you are walking on a road that already has millennia of stories.
Poggibonsi-San Gimignano stretch (12 km, 3 hours): gently climbs through hills with vineyards and olive groves. The arrival point - the medieval towers of San Gimignano - is one of the most satisfying on the entire route.
Gambassi Terme-Poggibonsi stretch (12 km, 3-4 hours): starts from Gambassi Terme (reachable by bus from Poggibonsi), crosses the Val d’Elsa countryside.
For those wanting to do the stretch one-way, there is the option of returning by bus or taxi.
Trekking in the Val d’Orcia: UNESCO panoramas
The Val d’Orcia has trekking routes with some of the most beautiful views in Tuscany. The terrain is flat-hilly, with trails that are not difficult but aesthetically rich.
Around Bagno Vignoni: routes along the Orcia stream, with the free thermal pools reachable on foot from the village. The Val d’Orcia landscape opens in every direction.
Pienza trails: routes starting from Pienza’s walls and descending into the cultivated Val d’Orcia hillsides. In spring, with fields of green wheat and cypresses, it is a landscape of rare beauty.
Monte Amiata: the highest extinct volcano in Tuscany (1,738m) has a well-equipped trail network. It is not a technically demanding summit, but the walk to the cross at the top is satisfying.
The Maremma routes: wild nature
The Maremma Park, between Grosseto and Ansedonia, offers trekking in a completely different environment: Mediterranean scrub, pine forests, wild beaches, rich wildlife (roe deer, wild boar, herons, flamingoes).
The park’s routes are well organised and require an entrance fee. The most interesting trails include those leading to the Torre di Castelmarino and the beach at Cala di Forno - reachable only on foot, far from any infrastructure.
From Poggibonsi, the Maremma Park is about 90 km away, one and a half hours by car.
How to organise a day out from Poggibonsi
The practical advice for organising trekking starting from Hotel Alcide:
- Choose the route the day before and check the weather forecast
- Set off after breakfast with a packed lunch (the hotel can help with preparation)
- Arrive at the start of the route by 9-9.30am
- Allow 3-4 hours of walking for a comfortable day
Equipment and recommended seasons
For Tuscan trekking you do not need special equipment:
- Trekking shoes (not trainers - the trails can be slippery)
- Layered clothing - mornings are cool even in summer
- Plenty of water - fountains on the trails are not always available
- Sunscreen - the summer sun is intense even at low altitude
The best seasons are spring (April-May) and autumn (September-October). In summer you can walk, but it is best to start early and finish by 12-1pm to avoid the heat.
Planning a trip to Tuscany?
Hotel Alcide is in Poggibonsi, in the heart of the Val d’Elsa.
25 km from Siena, 12 from San Gimignano, in the heart of Chianti.
The Ancillotti family has welcomed guests here since 1849.
