Hill Towns of Tuscany

This Tuscan hiking trip begins in the medieval and Renaissance hill town of Montepulciano. Upon arrival at the Montepulciano Train Station, there is an included transfer to your hotel in town, which is a few kilometres/miles away.

The historic center of Montepulciano is a traffic free zone so it’s a pleasant place to explore on foot. Admire the impressive views over the rolling Tuscan landscape that this trip will further explore over the coming days. The town is packed with elegant Renaissance buildings, ancient churches, and charming squares to sample a glass of local wine in while watching the world go by.

Please let us know your train's arrival time into the Montepulciano Train Station as soon as possible after booking so we can book your included transfer to your hotel accordingly.

Leave Montepulciano through one of the historic gates before heading out into the surrounding countryside. From the San Biagio Church, follow a quiet trail past vineyards and olive groves to the peaceful village of Montichiello. Why not pause here for a relaxed lunch or perhaps just a quick cappuccino before continuing to the hilltop town of Pienza.

Pienza is a UNESCO World Heritage Site with unique Renaissance architecture. The town is well known for its delicious pecorino cheese and truffles - a perfect spot to indulge in Tuscan treats!

For anyone wanting to take an easier hike today, it’s possible to schedule a transfer to Monticchiello (payable locally) and walk from here to Pienza.

Shorter hike from Montichiello: 6km (4mi) Ascent/Descent: 210m/230m (689ft/755ft)

Full hike from Montepulciano: 15km (9mi) Ascent/Descent: 470m/520m (1,542ft/1,706ft)

This is a particularly great hike as most of the time it’s possible to see both where you've been and where you are aiming for. Setting out on the hike from Pienza, admire views of Tuscan scenery with cypress trees, rolling farmland, and olive groves from across the valley. Along the way stop in San Quirico d'Orcia. A walled town with an elegant 12th century church and ornate gardens. It is a great place to spend some time exploring.

Pass through Vignoni with its iconic stone tower before arriving in the spa town of Bagno Vignoni. The thermal baths complex is the perfect location to soak up the Tuscan warmth and relax after a day’s hiking.

For anyone wanting to take an easier hike today, it’s possible to schedule transfer to San Quirico d'Orcia (payable locally) and hike from there to Bagno Vignoni.

Shorter hike from San Quirico d'Orcia: 5kms/3mi Ascent/Descent: 115m/220m (377ft/721ft)

Hike from Pienza: 14kms/9mi Ascent/Descent: 310m/490m (1,017ft/1,608ft)

A transfer in the morning at 0900am takes you to the medieval village of Castelnuovo dell'Abate and the Sant’Antimo Abbey, an impressive example of Romanesque Cistercian architecture. You have time here to explore this isolated abbey situated in a pastoral landscape. The exterior facade has a menagerie of animals, and the interior frescoes are very intriguing. From here, hike to the charming medieval village of Montalcino passing olive groves with fine views down the valley with its iconic Tuscan scenery and vineyards galore.

Montalcino is a classic Tuscan hilltop village with a complete circle of fortified walls. It is famous for it’s Brunello red wine, and its 16th century buildings are gloriously set with isolated cypress trees.

Ascent/Descent: 395m/180m (1,296ft/591ft)

Hike through the famous Brunello wine region, passing vineyards and olive groves, before entering the Tuscan landscape of the “Crete Senesi” with its rolling hills and farmland, dotted with patches of woodland and quaint little villages. The hike finishes at Fattoria Pieve a Salti Agriturismo near Buonconvento. It's an the ideal spot to relax after a long hike, or perhaps choose to explore a bit more and visit nearby Buonconvento. This photogenic village is still nearly entirely surrounded by the ancient city walls with only a small section being destroyed in World War II. There’s also a pretty little church and two small museums here - the Religious Art Museum of the Val d’Arbia and the Museum of Sharecropping.

Alternatively, there is an easier hiking option today, which is slightly shorter and a gentle downhill route into Buonconvento village. Spend some time exploring here before taking a transfer (payable locally) to Fattoria Pieve a Salti.

Shorter hike to Buonconvento: 13kms/8mi Ascent/Descent: 61m/421m (200ft/1,381ft)

Hike to Pieve a Salti: 15kms/9mi Ascent/Descent: 307m/538m (1,024ft/1,801ft)

Please note that on the rare occasions that the Fattoria Pieve a Salti Agriturismo is fully booked the accommodation will instead be in a small hotel centrally located in Buonconvento, in which case, you will take the shorter hiking option today.

A short but hilly day begins with a quick transfer at 0900am to Monte Oliveto Maggiore Monastery, an impressive abbey built of red brick and set in the rugged Tuscan landscape. The huge complex's main attraction are the frescoes in the cloisters, which portray the life of St. Benedict. After an early visit to avoid the crowds, walk back to the agriturismo near Buonconvento, perhaps stopping for a freshly made panini en route. Part of the route goes through shaded woodland as it explores more of the rolling Crete Senesi landscape.

Ascent/Descent: 236m/414m (774ft/1,358ft)

Please note that on the rare occasions that the Fattoria Pieve a Salti Agriturismo is fully booked, the accommodation will instead be in a small hotel centrally located in Buonconvento. There will be a transfer to return from the end point to the hotel at around 3pm.

Alternatively, for anyone not wishing to hike today you may wish to explore the charming village of Buonconvento or perhaps book a massage treatment at the Fattoria Pieve a Salti Agriturismo.

Today starts with a short transfer at 0900am to the well-preserved medieval fortified farm at Grancia di Cuna. It’s on the site of what was once a 12th century hospice and hospital for pilgrims on the Via Francigena. It’s worth taking the time to explore this historic site before beginning the hike to the UNESCO listed city of Siena.

Alternatively, it’s possible to take a transfer today (payable locally) to Colle di Malamerenda, which is closer to Siena. It’s an easier hiking option, which is both shorter and less hilly and will allow more time to explore Siena on arrival.

Hike through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. Walk past vineyards and olive groves along the way. Finishing at the main medieval gate to the city, the Porta Romana, makes for a fantastic photo opportunity. A memorable end to a great tour!

Shorter walk from Colle di Malamerenda: 9.8kms/6.1mi Ascent/Descent: 148m/53m (485ft/173ft)

Walk from Grancia di Cuna: 17.5kms/10.9mi Ascent/Descent: 258m/131m (846ft/429ft)

Alternatively today, you have the option to arrange a private transfer or grab a taxi (additional charges apply) to go directly to Siena and skip the hike, in favor of spending more time exploring this iconic city.

If time allows, we recommend adding an additional night in Siena, as this is an ideal location to relax in a café beside the main square or to explore the winding streets at a leisurely pace after completing this hiking trip.

From Siena catch the train to Rome, Pisa or Florence airports or perhaps continue to journey further within Italy. Tuscany combines perfectly with our coastal hikes of the Cinque Terre and Amalfi Coast or any of the Umbria trips.