Your itinerary
Day 1
Arrive in Chianciano Terme
Arrive at the Agriturismo La Pietriccia and enjoy a stroll to the old town, before your evening briefing by the owner, Stefano, and the first of many home cooked dinners.
Meals: Dinner
Day 2
Chianciano circular walk
Today’s walk takes you over the hills around la Pietriccia, with stunning views over Monte Marzolana and Chianciano Terme itself. The walk will finish in Chianciano’s medieval centre, from where you can make your way back to the hotel or spend more time exploring this ancient spa town.
Meals: Breakfast,Dinner
Day 3
A Walk to Lake Chiusi
As you descend into the Valdichiana, a mix of quiet lanes and gravel tracks provide perfect views of the vineyards and over to Monte Rufeno. Passing pretty farmhouses you make your way to the small town of Montallese, and from here you pick up the Sentiero della Bonifica, a long-distance path between Chiusi and Arezzo. This leads you to the charming Lake Chiusi, where you can enjoy the birdlife and perhaps lunch at the lakeside restaurant. You will be transferred back to the hotel.
Meals: Breakfast,Dinner
Day 4
Castiglioncello to the Hotel
A short transfer takes you to the charming village of Castiglioncello; once abandoned it is now restored with a hotel, a cafe and the interesting Etruscan burial site. From the village you follow a trail through the forest to pass wonderful viewpoints of the area, dropping down to Poggio Pietraporciana, a Nazi gun point in the war. Continuing through the Pietraporciana Nature Reserve you pass the Rifugio Pietraporciana, once owned by the Marchesa of Val d’Orcia, Iris Origo, who, during the war, cordoned off this area to create a neutral zone, which the allies, Nazis and partisans all obeyed. From here, a forest track takes you past a charming argiturismo before a trail along a dried up river alongside rocky cliffs and on to the outskirts of Chianchiano stopping at the Dopolavoro La Foce where an optional transfer back to the hotel awaits you. Alternative carry on walking along a narrow trail with wonderful views and past a model of an Etruscan farm, before arriving in Chianchiano Terme and a choice of following the white gravel roads passing farms or through the town to return to the agriturismo.
Meals: Breakfast,Dinner
Day 5
Free day
Today you have time to yourself, maybe walk into Chianciano Vecchia and visit the Etruscan Museum of Chianciano Terme, enjoy olive oil tasting at the agriturismo or use your voucher for the Thermal Spa and relax in the healing waters or treat yourself to one of their many treatments.
Meals: Breakfast,Dinner
Day 6
Walk to the Wine Town of Montepulciano
Today you walk to the wine town of Montepulciano, where you will be rewarded with stunning views across the Valdichiana. Follow a chestnut-laden track to meet the forest road, before following a track around the vines and farmlands up to Montepulciano. You will be picked up here, but before this, take time to explore the town, which is full of wine bars and shops and has plenty of tasting opportunities.
Meals: Breakfast,Dinner
Day 7
Pienza to Bagno Vignoni
After a short transfer to Pienza, take time to explore the town, it is one of the cheese capitals of Italy, and a beautiful mediaeval historic centre. Perhaps pick up a sandwich filled with porchetta or a slab of rich and creamy pecorino cheese. The walk takes you downhill from Pienza, crossing the stunning Val d’Orcia. It is an easy walk following a well-marked trail, giving you the chance to take in the views of mediaeval towns, rolling hills and rows of cypress trees. You will reach Bagno Vignoni then follow the river Orcia before climbing up to the town passing the spring baths and the old mill, before arriving in the Roman town, with its large baths in the centre of town. Perhaps treat yourself to the hot waters of the Hotel Posta Marcucci, where the baths come with a view! We transfer you back to the hotel for your final night of Stefano’s lovely food.
Meals: Breakfast,Dinner
Day 8
Leave Chianciano Terme
Leave Chianciano Terme
Meals: Breakfast
What’s included
What’s not included
Additional information
Food
Tuscan food is based on the Italian idea of ‘cucina povera’ (poor cooking); simple inexpensive meals that can be made for large groups. Whilst this was once dictated by the economy and expense of the produce, the tradition has remained. The cuisine of this region doesn’t use complicated seasonings or elaborate recipes, and instead focuses on fresh, high quality ingredients that allow the natural flavours in each dish to shine through. Typical dishes include fagioli con salsiccia (cannellini beans with sausage), tagliatelle al tartufo (pasta in a truffle sauce), bistecca alla Fiorentina (a T-bone steak which is only cooked blue
are and often large enough to share!), pici (a fat, handmade spaghetti, often served with tomato and garlic sauce or game meat). Don’t miss the local cacio and pecorino cheeses and sample the famous wines: Nobile di Montepulciano and Brunello di Montalcino.
Bagno Vignoni Thermal Pools at Hotel Posta Marcucci
Soak in the village’s renowned baths with a session at Hotel Posta Marcucci, where you can soak in panoramic thermal pools gazing toward the Val d’Orcia. Warm waters and soft light invite unhurried relaxation after your walk.
Part of a living Roman spa tradition, these pools are especially atmospheric at dusk, when sunset over the valley casts the hills in amber. Access is at additional cost and bookable during your holiday.
Farm-to-Table Tuscan Dinners at La Pietriccia
Taste the region through four courses of farm-to-table dinners prepared by Stefano and his team, using seasonal vegetables, grains, and meats sourced on site or from trusted neighbours. Expect soulful Tuscan classics that let ingredients lead: rustic soups, handmade pici pasta, slow-braised sauces, and countryside desserts perfumed with garden herbs.
Learn how Tuscany’s ‘km 0’ cooking elevates simplicity and quality, and savour local cheeses like cacio and pecorino. The candlelit dining room and hillside views complete a grounded culinary experience rooted in rural rhythms.
Wine, Olive Oil & Local Produce Tasting at the Agriturismo
Sample the territory with a guided tasting that pairs cold-pressed extra-virgin olive oil with artisan breads, local pecorino cheeses, and seasonal specialities from the farm. Sip a curated flight of sample regional wines while learning how soil, exposure, and tradition shape flavour.
Discuss harvest cycles, milling techniques, and ageing styles that define Tuscan staples. This convivial session highlights small-scale production and the bonds between land and table.
Chianciano Terme Thermal Spa Entrance
Unwind with included access to Chianciano’s celebrated spa culture and soothe in thermal waters long prized for relaxation. Drift between warm pools and quiet zones designed for calm after days on the trail, letting mineral-rich steam ease walking muscles.
Soak up the Roman spa heritage of Chianciano Terme as you enjoy contemporary wellness facilities—think thermal cascades, steam rooms and relaxation areas. It’s an atmospheric pause that complements Tuscany’s slower pace.
Chianciano Hills & Medieval Centre Walk
Explore undulating lanes and panoramic ridge paths surrounding Chianciano Terme, with wide views toward Monte Marzolana and the Valdichiana. The route leads to stone lanes and small piazzas inside the medieval centre of Chianciano Terme, where fountains and facades reveal the town’s spa legacy.
Wander past churches and shuttered palazzi, noticing how thermal waters shaped civic life through centuries. Pause to pause for photos and reflection before returning at your own pace.
Lake Chiusi & Sentiero della Bonifica Walk
Follow the historic Sentiero della Bonifica, a level pathway tracing canals and countryside between Arezzo and Chiusi. The route opens onto tranquil Lake Chiusi, where reed beds shelter waterfowl and the mirror-still surface reflects vineyard-dotted hills.
Watch for herons and grebes as you skirt the shore, with the ancient Etruscan city of Chiusi nearby. Gentle gradients and broad skies make this a contemplative, nature-rich outing ideal for an unhurried lunch by the water.
Pietraporciana Nature Reserve & La Foce Trails Walk
Walk from hilltop Castiglioncello past an Etruscan burial site into the beech woods of the Pietraporciana Nature Reserve. Clearings reveal cypress-stitched horizons and wartime echoes at Poggio Pietraporciana, once a strategic gun point.
Learn how writer Iris Origo established a wartime “neutral zone” here, and continue toward La Foce with cypress-lined viewpoints over sculpted fields. This route blends layered history with classic Val d’Orcia scenery.
Walk to the Wine Town of Montepulciano
Ascend through chestnut groves and vineyard tracks to the storied wine town of Montepulciano. Stone gates usher you into steep lanes flanked by Renaissance palazzi, artisan boutiques, and small enoteche.
Climb toward Piazza Grande for sweeping views across the Valdichiana and discover cool, brick-vaulted Vino Nobile cellars tucked beneath noble houses. It’s a rewarding hike that pairs countryside tranquillity with hill-town drama.
Pienza & Val d’Orcia Walk to Bagno Vignoni
Start in Pienza’s harmonious lanes—an exemplar of humanist urbanism—before tracing farm tracks across the UNESCO Val d’Orcia. The path undulates past wheat fields and cypress-lined ridges, with photogenic hill towns punctuating the horizon.
Arrive at Bagno Vignoni, famed for its central thermal basin, and follow the River Orcia past mills that once harnessed the flow. This gentle traverse links the Pienza historic centre to a spa village steeped in timeless ritual.
Montepulciano Vino Nobile Cellar Tour & Tasting
Descend beneath historic palazzi for a guided cellar tour where Vino Nobile matures in oak. Guides explain vineyard sites, grape selection, and ageing as you move through cool tunnels stacked with barrels.
Conclude by sampling regional wines, comparing styles from different estates and vintages, and learning food-pairing tips for Tuscan classics. This experience is at additional cost and bookable during your holiday in Montepulciano.
Chianciano Terme Etruscan Museum Visit
Visit the Etruscan Museum in Chianciano Terme to explore artefacts from nearby necropolises and sanctuaries. Displays reveal craftsmanship in bronze, ceramics, and jewellery, tracing everyday life and belief in ancient Etruria.
See artifacts from ancient Chiusi, including painted terracotta urns and votive offerings that illuminate water cults and funerary rites. Entry is at additional cost and payable locally, with visits easily arranged during your stay.
Welcome Briefing & Orientation at Agriturismo La Pietriccia
Meet your hosts for a warm orientation briefing on the terrace at La Pietriccia, overlooking Chianciano’s hills. Get practical tips on local paths, dining culture, and how best to pace the week’s routes through the Valdichiana and Val d’Orcia. This relaxed session helps you settle in and connect with Stefano’s passion for the land and its produce.
Familiarise yourself with the Headwater navigation app, trail notes, and safety guidelines while hearing about the agriturismo’s ‘km 0’ cooking philosophy. It’s an inviting introduction that frames the landscapes you’ll explore and the traditions you’ll taste.