Independent arrival in Orvieto, which is a direct one-hour train ride from Rome or two hours from Florence. Orvieto’s upper town is mostly pedestrian, and the streets are alive with boutiques, cafes, and trattorias that are frequented by the locals who live in the city’s medieval houses. Meet your guide(s) and the rest of the group at 6:30 tonight for drinks followed by dinner at a local trattoria. Overnight Orvieto. Hotel and dinner included.

Morning transfer to the start of our hike. Follow paths and country roads as they gently meander towards the Lago di Bolsena, a dramatic volcanic crater lake. We stop in the charming town of Bolsena itself, once an important Roman outpost. Make your way down from the Rocca (castle) through narrow cobblestone streets to the lower town, where you enjoy a seafood lunch by the water. Afterwards, transfer to your home for the next 2 nights, the charming Locanda Pantanello (or similar), a family-run farm hotel. You’ll have time to rest before a cooking lesson where you will learn the secrets of local cuisine from our hosts. Enjoy the fruits of your labour as we dine on their terrace. Overnight at the Locanda Pantanello in Pitigliano. The Hike: 8 km (5 mi), about 2 hrs. Hotel, breakfast, lunch, and dinner included.

A short morning transfer takes you to the enchanting village of Sovana, where you visit the medieval castle, Renaissance palazzi, and beautiful 12th century cathedral before departing on foot and travel back in time as you hike along the 3,000-year-old Vie delle Cave, which were carved from the tufa rock by the Etruscans. You will see the intriguing Etruscany tomb complexes of "Ildebrando" and "La Sirena" and then have a picnic lunch and wine tasting at a family-run winery. We visit their wine cellar, which is carved directly into the local stone. A short transfer takes you to the sensational town of Pitigliano, which rises up from the surrounding woodlands on a tufa plinth. Explore the medieval alleyways and enjoy the views before returning to your country hotel to relax by the pool. Dinner is another delicious meal made from ingredients and produce from the farm. Overnight Pitigliano. The Hike: 12 km (7.5 mi) Hotel, breakfast, picnic lunch, and dinner included.

A 90-minute transfer brings you to Bagno Vignoni, famous in both Roman and Renaissance times for its hot springs. Your hike begins here and takes you past ancient mills and bridges to the river before heading up again to the imposing castle of Rocca d'Orcia. We eventually reach the castle itself and enter the grounds to enjoy the sweeping views that medieval soldiers once commanded hundreds of years ago. We have a picnic lunch in a small piazza and then transfer to the hilltop village of Montalcino. Your hotel, the Vecchia Oliviera, is perched on the hillside just outside the 14th-century archway that leads into the historic centre. After a dip in the pool, relax in the garden and take in the uninterrupted view over a patchwork of vineyards, olive groves, and golden wheat fields that lay far below you. Dine tonight in a wonderful small restaurant that features ancient beams, terracotta floors, and a wine list that has a vast array of superb vintages of Brunello di Montalcino. Overnight Montalcino. The Hike: 11.5 km (7 mi), about 2hr45 mins, 460 m (1,500 ft) elevation gain. Hotel, breakfast, picnic lunch, and dinner included.

Our hike leaves directly from the hotel. Stroll through the cobblestone streets of Montalcino, pass the castle and head into the vineyards and woods beyond the village. Become a modern-day pilgrim as you make your way on foot to the beautiful 12th-century abbey of Sant’Antimo, an outstanding example of Romanesque architecture set in a serene setting amongst ancient olive trees. We have lunch at a local trattoria in the village of Castelnuovo Dell'Abate followed by a very special wine tasting at Azienda Uccelliera, one of Italy’s best producers of Brunello di Montalcino. You will taste different vintages directly from the barrel and learn about and taste the importance of “terroir” in determining the taste and style of wine in your glass. Return by van to Montalcino. We have a "free night" tonight so you are free to dine where you like. Overnight Montalcino. The Hike: 12.6 km (7.8 mi), 250 m (800 ft) elevation gain. Hotel, breakfast and lunch included. Dinner not included.

A short transfer after breakfast brings us to the small Renaissance town of Pienza, silhouetted against the sky with its proud cathedral watching over the Orcia valley. It’s another UNESCO World Heritage site thanks to the efforts of Pope Pius II, who was born there. After becoming pope in 1458 he transformed his humble village into a papal retreat and a centre of Renaissance culture, architecture, and town planning. We hike out of Pienza, beneath its defensive walls and into the strikingly beautiful countryside. Our destination is the Cappella della Madonna di Vitaleta, a perfect chapel set amongst golden wheat fields and flanked by two sentinel cypress trees. Nearby, a renovated farm house is now an improbable and discreet osteria where we enjoy a mid-morning break. We loop back to Pienza and then have a short transfer to the hilltop farm “Podere Il Casale” for an unforgettable lunch. Continue on to Montepulciano this afternoon where you'll have time to explore the town or just relax with a gelato or glass of wine before returning to our hotel, the Relais Il Chiostro. A former Franciscan Convent dating back to the 13th century it is now a four-star hotel with elegant rooms and a panoramic terrace overlooking the dramatic landscape below. Overnight Pienza. The Hike: 10 km (6 mi), 236 m (774 ft) elevation gain. Hotel, breakfast, lunch, and dinner included.

We have a more leisurely start this morning so you can enjoy a relaxed breakfast, perhaps even a second cappuccino in the sunny main square before setting off for a beautiful loop hike departing from the historic Villa La Foce. Set amidst 3,500 acres of farmland, the 15th-century villa was bought in the 1920s by Antonio and Iris Origo, who set about restoring the dilapidated villa and gardens. During WWII, at great personal risk, the family sheltered and hid escaped Allied P.O.W. and Italian Partisans from the Fascist Italians and the Nazi occupation. The front passed through the estate, and the villa was held as a defensive position by German paratroopers. Iris Origo’s fascinating first-hand account of this time can be read in “War in the Val d’Orcia.”  After lunch at their wonderful trattoria, you’ll have a guided visit of the gardens*, which are considered to be among the finest in Italy (*if possible: the gardens are frequently closed for private events). Return to Pienza for some free time, and then dine at one of the town’s most beloved trattorias. Overnight Pienza. The Walk: 8 km (5 mi), 250 m (800 ft) elevation gain. Hotel, breakfast, lunch and dinner included.

We offer one group transfer after breakfast this morning to the Chiusi train station in time for 10 a.m. departures to Rome, Florence, and beyond. Breakfast and transfer included.

Please note: Some details of the itinerary may change according to the departure date of your tour. Whenever we run a tour we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes they are bad, like a trail has been washed away. The result is that we sometimes change our itinerary to improve it by adding new wonderful elements to the tour or by removing something that does not work anymore. Rest assured, our goal is to always provide you with the best possible experience. We will advise you of any changes to the original itinerary prior to departure.  

The hikes in Tuscany cover a variety of terrain, from trail to dirt road, with many rolling hills to climb or descend. We have designed the trip so that there is always some free time in the late afternoon so you can relax, read, or enjoy the towns where we stay. Breakfast is included every day, and dinners reflect the excellent traditional food of the region. Daily distance between 8 and 16 kms.