Southern Tuscany

Val d'Orcia on foot

Walking out of Pienza on a clear morning, the Val d'Orcia opens up below in waves of clay hills, lone cypresses and ploughed earth the colour of terracotta. This is southern Tuscany — the postcard version, but earned by walking it rather than driving past. On Foot Holidays runs a self-guided route that links the Renaissance hilltop towns of Pienza, Montepulciano and Montalcino, with stops in places most coach tours never reach: Bagno Vignoni and its open-air thermal baths, Castello Ripa d'Orcia perched above the river, the Romanesque Abbazia di Sant'Antimo standing alone in a fold of olives.

Days out range from three and a half to six hours, with the option of four, five, six or seven nights depending on how much ground you want to cover. The walking is steady rather than punishing — long climbs to the towns are repaid in cold beer, vermentino and a piazza to sit in. Siena anchors the route at the northern end; the Piazza del Campo is worth a full afternoon before or after the walking begins.

What the days look like

Routes thread through vineyards, oak woods and the white gravel strade bianche that crisscross this part of Tuscany. You'll pass under Montepulciano's walls (Vino Nobile country), drop into the Orcia valley, and finish most days in a town small enough to walk end to end in ten minutes. Meals lean on what's local — pici pasta, pecorino di Pienza, Brunello di Montalcino at the heavier end, Rosso di Montalcino if you'd like to walk in the morning. Luggage is moved between hotels each day; you carry a daypack and a bottle of water.

Wayfinding is handled through On Foot's app, which has clearly become the operator's standard kit — repeat walkers in the testimonials mention it constantly, often more warmly than the scenery. GPS tracks, daily notes and a local contact (Daniele, in this region) sit behind it, with paper backup if you'd rather not stare at a phone.

Booking and what's included

Prices are per person and start at £775 for the four-night route, £885 for five, £975 for six and £1,140 for the seven-night version. The longer the trip, the better the value per day. Included: hotel accommodation, breakfasts, luggage transfers between stops, the route notes and app, and access to the local contact during your walk. Not included: flights, transfers to Siena or your start point, lunches, dinners and the wine you will inevitably buy.

It suits adult walkers comfortable with a few hours on their feet across rolling country — first-timers to multi-day walking manage it (the testimonials make this clear), as do experienced hikers looking for something less strenuous than the Dolomites. April-May and September-October are the natural windows; July and August are hot enough that the morning starts get early. Solo walkers do this route, but it lends itself well to couples and small groups of friends who'd rather sit down to dinner together than alone.