Walking the Tuscan Hills

You will be welcomed by us at the train station in Montepulciano for the transfer to your comfortable hotel. Here, we’ll go over the tour with you, supply an information package, answer your questions, and give you a few tips! The rest of the day you can explore Montepulciano to walk Il Corso and explore these side streets. You’ll come across small restaurants, boutique shops, and quiet corners away from the busier areas. 

From the San Biagio Church, which is in the outskirts of town (and certainly worth a visit), the dirt road will take you to lovely Monticchiello, a nice little village immersed in the Italian Crete Senesi, the region In Tuscany with clay hills and grand open valleys. We can stop here for a tasty Tuscan lunch or just a cappuccino before continuing on to the perfect Renaissance town of Pienza, an architectural jewel famous also for its cheese, the pecorino di Pienza. Pienza was planned and built from 1459 – 1462 by the famous Florentine architect Gambarelli at the request of Pope Pius II. Walking through the narrow streets of this walled city is a photographer’s delight, and the cathedral and Pope’s residence are well worth a visit. You’ll stay tonight in a pleasant hotel in town.

We’ll leave Pienza today on a dirt road toward the village of San Quirico d’Orcia. This fortified village is one of the least known and best-preserved historical centers in the Sienese Province. It was an important stop for pilgrims on the Via Cassia, the way to Rome. The 15th century walls are still almost totally intact. They enclose the magnificent 13th century Romanesque Collegiate Church with a famous stained glass window and hand carved wooden choir-stalls. The main street of San Quirico, Via Dante Alighieri, traverses the town and contains a number of well-preserved medieval houses. Most notable is the Renaissance Palazzo Pretorio. There is plenty to see and photograph in this quaint village, including the Horti Leonini, an unusual public park with a Renaissance style garden created by Diomede Leoni in 1580. From San Quirico, a small road leads up through beautiful countryside to the tiny village of Alto Vignoni, now almost totally abandoned. It has a truncated medieval tower and a Romanesque church on the edge of the hill. You’ll definitely want to take a short stop to admire the spectacular view! From Vignoni, we’ll wind our way down to other points of interest in the beautiful Orcia Valley: the stony river bed, the castle of Ripa d’Orcia, and the ancient spa of Bagno Vignoni. Here you can soak your feet in the warm sulphurous waters that bubble up into a large pool constructed by the Medici family in the Piazza. Tonight you’ll stay in Bagno Vignoni or in an agriturismo 2 km from town along your trail.

We’ll have a beautiful but quite strenuous day of walking today along dry river beds in a rather wild but stunningly beautiful landscape to reach the inspiring Benedictine Abbey of Sant’Antimo. The Abbey was founded by Charlemagne and had a period of great splendor in the first centuries of this millennium. You can still hear the original Gregorian Chants sung by the 5 remaining monks in the abbey. In the evening we’ll reach Montalcino, the capital of Brunello wine. It’s a nice medieval town with plenty of shopping possibilities. You’ll stay tonight in a hotel in Montalcino.

Today we will be walking through scenic Brunello vineyards and shimmering olive tree orchards. You can choose a shorter version, spending the night in a 3-star hotel in Buonconvento, or a longer route through a beautiful Crete Senesi landscape where you’ll spend the night in a nice agriturismo 3 km from Buonconvento. Buonconvento is an important agricultural center on the gentler side of the Sienese Clay Hills. It already flourished in ancient times, thanks to its particular geographical situation at the confluence of the Arbia and Ombrone rivers and along the all-important medieval Via Francigena Pilgrim Route on the other.

This short day is full of rises and dips. Oliveto Maggiore is one of the best known Benedictine monasteries in Tuscany. The monastery was founded for hermits in 1313 and was suppressed by Napoleon in 1810. After restoration, it was made a national monument with some monks remaining as caretakers. Old pines surround the cloister and the walls are decorated with gorgeous, well-preserved frescoes detailing the history of St. Benedetto and the Benedictine order. Because of the monastery closing time you’ll start the day with a transfer so you can visit the abbey before the tourist rush hours, then start walking back toward your hotel or agriturismo. You can stop for a light snack at Chiusure, the first village on your way back. There is a small “Alimentari” which now has upgraded to a wooden terrace where they serve delicious, freshly made panini. 

After Florence, Siena, once Florence’s most powerful rival, is by far the most interesting town in Tuscany. Because of its many treasures we recommend two days here for an adequate visit. Highlights are the dazzling cathedral and the Palazzo Pubblico, both gorgeous Gothic buildings, and the Piazza del Campo, one of the most remarkable squares in Italy and the site of the yearly “Palio” horse races. Enjoy your last night of your tour!

Your tour ends after breakfast with departure from Siena. The train station in Siena, where you might like to catch a train to Florence, Rome, or Milan, is 5 minutes away by cab. Busses to Florence leave from the square right around the corner from the hotel.