Tuscany Walking Adventure

DAY 1 > MONTEPULCIANO

We meet after lunch in the beautiful town of Montepulciano, a medieval city full of winding, cobblestoned streets and boasting plenty of shops, restaurants, and cafes. The city, which has ancient roots dating back to Roman times and the pre-Roman Etruscan people, is strategically placed on a hillside with a castle that protected the trade routes and farming fields below. We will take an introductory exploratory walk on the side roads and small paths of the city and the countryside just below, with a stop at the Cantina Dei winery for our first taste of Vino Nobile di Montepulciano. This night we will eat a delicious Italian meal together, as we will each night of the tour.
Walking Distance: 5 KM

DAY 2 > MONTICCHIELLO + PIENZA

This is our first classic Tuscan walk, with views of lovely small towns as we amble across the countryside of rolling hills, dotted by stone houses and cypress trees. Our walk takes us into the medieval walled village of Monticchiello. After exploring this cute village, you can opt to eat on your own in town, with one option being at Ristorante Dario, who is a good friend of our guide Giovanni, or Osteria la Porta which has a beautiful view over the Val d'Orcia below. Don't eat too much because after lunch it is back down into the valley and on to the Podere di Casale goat and sheep cheese making farm. We then walk up again to the small hilltop city of Pienza. When Silvio Piccolomini became Pope Pius II in 1458 (before Columbus reached America), he decided to create a model Renaissance town and the resulting Pienza still boasts the central piazza, the towering cathedral, and the parks overlooking the valley below. In Pienza, Marco and his family have hosted our groups at his Piccolo Hotel for years and we'll be happy to rest while toasting the sunset from the hotel garden.
Walking Distance: 14 KM

DAY 3 > SAN QUIRICO D'ORCIA + BAGNO VIGNONI

After breakfast we will descend from Pienza into the scenic Orcia river valley, walking through postcard landscapes of rolling hills and deep golden wheat fields. Along the route we will pass through the village of San Quirico d'Orcia, which has much of its ancient wall systems remaining but since it is often overlooked by tourists, seems more real than some of the nearby towns. You will be able to explore the town and eat lunch on your own. Ristorante Trattoria Al Vecchio Forno is a good option. First you might choose to visit the Birrificio (brewery) San Quirico, where you can sample Italian-style craft beers - think fruity, spiced, and amber rather than hop-heavy IPAs. After lunch we continue our walk to Bagno Vignoni, a beautiful "resort" town famous for its hot springs, where the traditional piazza is instead a large pool. You can choose to soak in the public Parco dei Mulini or in the private baths connected to our hotel, the Hotel le Terme.
Walking Distance: 14 KM

DAY 4 > CASTELNUOVO + MONTALCINO

Today we depart the Val d'Orcia and head into new scenery, passing through evergreen woods and next to vineyards on small paths and country roads. En route we will visit the Mastrojanni winery to learn about and taste the famous Brunello di Montalcino wines. After the tasting we will stop in the small village of Castelnuovo, which has a number of lunch options. Our destination in the afternoon is the Abbey of St. Antimo, a beautiful church founded by Charlemagne in 781, which has inspired many poets and painters and where Benedictine monks chant daily. Because of the length of walk to the abbey (perfect!) and the absence of nearby lodging, we will shuttle in the van to our hotel tonight in Montalcino, another beautiful medieval town and famous for both its Fortezza (fortress) and the sublime Brunello di Montalcino wine we tried earlier in the afternoon.
Walking Distance: 14 KM

DAY 5 > BUONCONVENTO

We start our walk heading downhill out of Montalcino, passing some of the vineyards that make the local wine so famous. Our track is on small gravel roads and dirt walking paths, through forests and countryside dotted with farmhouses. Lunch will be at the town of Buonconvento, a charming spot off the normal tourist route and a great place to see real small-town life in Italy. The small city is intriguing, having been built not on a hilltop but instead in a valley at the confluence of two rivers, an important location for trade. The walled town is perfect for exploring and finding a bite for lunch. After lunch we will head uphill to the lovely agriturismo of Pieve a Salti, a working farm that houses guests. Daniela and her crew have been hosting us here for years, and the farm's delicious home-grown products make for a fresh-as-can-be dinner.
Walking Distance: 15 KM

DAY 6 > MONTE OLIVETO + SIENA

We start heading downhill from the ridge top location of Pieve a Salti, walking on small paths through the forest. We then reverse and start climbing uphill to the Abbazia di Monte Oliveto, an abbey founded in 1313 by a Sienese nobleman. The still-operating abbey is a Benedictine order monastery with world-renowned frescoes and carvings by Sodoma, Signorelli, and Fra Giovanni da Verona. After a visit to the monastery, we will shuttle to Siena, considered by some to be the best preserved medieval city in Europe, a true masterpiece of art and architecture with its Gothic Duomo, museums, and famous buildings. If you have time this afternoon, our guide can take you to the Museo Civico Siena, housed in the Palazzo Pubblico, a building built around the end of the 12th century to house the nine lords who ruled the Republic of Siena. The museum has frescoes from the 12th and 13th centuries.
Walking Distance: 12 KM

DAY 7 > SIENA

On our final day, we eat breakfast and then enjoy a walk of Siena, discovering the ancient buildings and the untrammeled side alleys. We'll visit the shell-shaped square "Il Campo", the scene of the mad horserace "The Palio" which you might have heard or read about. We'll also stop at the Torre del Mangia, an 87 meter high tower built in the 1300s. After our walk, we will check out of the hotel. You are free to continue on your journey, stay another night in Siena, or head back towards the airports of Rome or Florence.
Walking Distance: 3 KM