Italy: Quiet Pathways of Tuscany​

After breakfast today we shuttle about 30 minutes outside Siena to the medieval village of San Guzme, one of the oldest and best preserved castle-villages in the Chianti region. From here we start our loop in the scenic wine region, passing by the beautiful manicured grounds of Villa Arceno. For lunch we’ll enjoy a picnic in San Guzme, where our walking afternoon options start. All options take us to the foot of the famous Castello di Brolio, the imposing castle of the Ricasoli family. Bettino Ricasoli, a famous 19th-century politician has been credited with the development of the celebrated Chianti wine varietal.  From here, we can walk an easy stretch to the ancient village of San Felice. This former Chianti village is now a Relais & Chateux hotel. Here, our hosts will take us to the underground winery for a wine tour and tasting.  Later this afternoon, we shuttle back to Siena to relax and dine on our own.

Take an early morning stroll around Siena and get a genuine feel for life in the city as locals begin their day with a cappuccino or two.  Walk the quiet cobblestone streets back to our district, Contrada Della Chiocciola, and have breakfast at our hotel. Later choose to spend the morning shopping and exploring on your own or to join our walk from Colle Val D’Elsa to Strove. This stroll follows a stretch of the ancient pilgrimage route ‘Via Francigena’ connecting Canterbury in England to Rome. We walk gentle, downhill and flat country paths in the Elsa Valley over iron-rich, sienna-hued soil.

Have lunch on your own and then choose to spend the afternoon in Siena or walking from Strove to the walled city of Monteriggioni through open sunflower fields and macchia shrub. Built in 1213, the Castle of Monteriggioni could not be conquered by the Florentines in spite of their frequent attacks. It fell only when the captain of the troops betrayed the Sienese. Stepping inside, we glimpse life as it was 800 years ago. A short shuttle will take us back to our hotel. Dinner is on our own tonight.

This morning a 45-minute shuttle takes us to the 14th-century Olivetan abbey of Monte Oliveto Maggiore. In the Great Cloister, we admire the frescos painted by some of the most famous artists of the Sienese school. Here we start our walk to the tiny stone village of Chiusure, making our way along a spectacular lunar-like region of ‘Crete Senesi’. Lunch is on your own in Chiusure before we continue walking on the crest with amazing views of the valley and abbey from afar. Or, you might opt to shuttle to San Giovanni d’Asso, another picturesque setting with the remains of a castle and a truffle museum.

Later shuttle to nearby Pienza and settle in our historical hotel, located in the ancient cloister of the San Francesco church. Before dinner, follow our tour leaders in an orientation walk of this elegant small 15th century town, hailed for its Renaissance layout. Just outside of town, discover, the peaceful Pieve di Corsignano before gathering for a group dinner at a local trattoria. Taste the famous local ‘pici all’aglione’.

This morning we shuttle to the hilltop village of Montalcino, famous for its Brunello wine. Ascend to its topmost “fortezza” for spectacular countryside views of the Orcia Valley, a UNESCO World Heritage Site. Then, visit one of the many enotecaor wine cellars.

This morning a short shuttle takes us to our next starting point, San Quirico d'Orcia. This fortified, little town on the northern edge of the Orcia Valley is on the ancient pilgrimage route of Via Francigena, which brought fame and wealth to the city. We admire the Romanesque church, Collegiata, with three doorways featuring fine stone carvings. We then regroup in the Leonini Gardens for a stretching class before starting our walk. Enclosed within the ancient ramparts of the city, the gardens are a particularly lovely spot. They retain the original Renaissance structure and prove to be a well-preserved example of the traditional Italian-style garden.

In the afternoon, you can choose to remain in Bagno Vignoni and opt to enjoy the waters at the nearby Hotel Posta, in the natural springs or you can continue walking on an optional, more challenging route.

Later, we drive back to Pienza. Get ready for a farewell and festive dinner in a local ristorante in the nearby hilltop village of Monticchiello, where we take in our last views of the Orcia valley at sunset.