Day 3
After breakfast we take the short drive to Siena for an enriching guided tour of its treasures. Not only was it the capital of the Republic of Siena, it was also one of the world’s wealthiest cities. A jewel of remarkably preserved Italian-Gothic and medieval architecture, Siena truly deserves its World Heritage status. The city centres on the main square, Piazza del Campo, an architectural work of art formed in a half-moon shape, lined by tall, striking buildings, whose gracious and varied facades have a unique charm. With its abundance of pavement cafés, it’s the perfect place to sit and reflect on the city’s sheer beauty.
Siena is equally famous for the Duomo, one of Italy’s most intricate and fascinating cathedrals. The exterior is built from black and white marble, and the west façade offers a fine example of workmanship. The interior is even more breathtaking, with splendid stained-glass windows, and paintings and sculptures by leading artists, including the young Michelangelo. Impressive as it is today, the Duomo was set to become the largest church in Christendom in the 14th century, had plans for the nave been completed. Little was built in Siena thereafter but, fortunately, even less was demolished, leaving a wonderfully preserved city for us to appreciate today. The afternoon is then yours to shop, people-watch or explore further before tonight’s dinner at a restaurant in Chianciano.
Day 4
Today’s walk starts in San Giovanni d’Asso, a hilltop village dominated by a sand-coloured castle that houses a museum dedicated to the white truffles for which the region is known. We set off through the lunar-like clay hills of the Crete Senesi, where woods of oak, alder and hazel blend with fields and farmsteads linked by cypress-lined avenues, which punctuate the pastel landscape with bold dashes of green. Misty mornings can lend an ethereal feel as distant hills and ridges shimmer in and out of focus, and the calming birdsong is interrupted by the occasional splutter of a farmer’s van. Along the way we will cross a number of smaller valleys, where the inclines can be steep at times.
After a couple of hours of walking along country tracks through this beautiful landscape, we arrive in the enchanting walled village of Chiusure. From its panoramic terrace we can gaze across the sweeping valley and see the red-brick Monte Oliveto Monastery nestled in an emerald sea of trees. Here we have a choice between an easier route that takes us directly to the monastery and a slightly more energetic walk via the remains of a medieval irrigation channel.
We take a well-earned break at Monte Oliveto and enjoy an included lunch on the monastery grounds. After lunch, we visit the 14th-century monastery, the mother-house of the Olivetans. Marvel at the grand cloister’s superb frescoes depicting the life of Saint Benedict and observe the intricate intarsia inlay of the church’s choir stalls. Monks still live here in quiet seclusion and follow the Benedictine maxim of ora et labora, prayer and hard work. They produce their own wine and herbal remedies using ingredients from the monastery’s vineyards and gardens.
Duration: 2 hours 15 minutes (4.3 miles)
Altitude gain: 755 feet
Terrain: country roads
Moderate option: an additional 0.9 miles and additional 230 feet in altitude
Day 5
This morning we cross the border to the neighbouring province of Umbria and its bustling capital, Perugia, whose fascinating escalator system connects the lower town to the historic core above. A wander along the Corso Pietro Vannucci is a treat for the senses, as its traffic-free status allows the subtler sounds and smells of local life to come through. This wide avenue leads past shiny boutiques and tiny shops to Piazza IV Novembre. The showpiece of the city, this flagstone square boasts the Gothic San Lorenzo cathedral, the 13th-century Palazzo dei Priori and the ornate Maggiore fountain. Fanning out from the square is a jumble of narrow alleys lined with pastel-hued buildings, providing plenty of places to people-watch over a craft beer, chilled glass of Orvieto Classico or scoop of creamy gelato. From Piazza Italia, you can take an escalator down a level to Perugia’s underground world, hidden within the 16th-century Rocca Paolina fortress, where you can stroll through the network of alleyways and remains of houses that became the foundations for the fortress above.
After lunch we travel a short distance to nearby Passignano on the northern shores of Trasimeno, the fourth-largest lake in Italy. You have free time to stroll along the lakeside promenade and explore the town, seeing its Roman castle and historic churches. Or hop aboard a ferry to Isola Maggiore and enjoy the serenity of the island, where Saint Francis is said to have spent time as a hermit.
This evening we visit a small organic farm, where Flavio and his family have spent the past 30 years reintroducing and preserving traditional and sustainable farming methods. Surrounded by orchards and fields, with horses and donkeys grazing in the paddock next door, this 17th-century homestead is simply idyllic. We’ll sit down in the traditional farmhouse to a wholesome dinner made almost entirely using produce from the farm. Drinks will be served on the terrace if the weather is fine, so we can enjoy the superb views over sparkling Lake Trasimeno as the sun sets.
Day 6
After a morning at leisure, this afternoon we make our way to the medieval hilltop town of Montepulciano, renowned for its revered Vino Nobile wine. Continuously inhabited since Etruscan times, the town boasts ancient churches and Renaissance mansions, whose cellars store row upon row of barrels containing aging wine. There are plenty of independent wineries offering informal tastings, as well as smart boutiques and cosy restaurants. A stroll to Piazza Grande affords spectacular views of the surrounding valleys and hills veiled with Montepulciano’s prestigious vineyards.
Alternatively, you may wish to continue spending your day at your own pace. Perhaps explore further and visit the old town of Chianciano, a charming gem off the beaten path with some of the finest hot springs in all of Italy, and indulge in a pamper session at a spa. For lunch try a dish of pici, hand-rolled pasta resembling fat spaghetti, which originates in Siena and is usually topped with a rich porcini sauce or flavoursome ragù.
Day 7
This morning we walk off breakfast in the ancient village of Monticchiello, the site of dramatic last stands against Florence in the 16th century and the fascists in World War II. The battles of yesteryear are a far cry from the idyllic reality of today: locals meet in attractive squares framed by quaint stone houses with flower-festooned balconies, while pets laze nonchalantly in the sun.
We follow graded farm tracks through iconic Tuscan countryside of wheat fields dotted with poppies and cornflowers. This is where the opening scenes from the film, Gladiator, were shot – and for good reason, as it seems as though little has changed here over the centuries. Most of the walk is gentle, but the final approach has a steeper incline.
Within a couple of hours we’ll have reached Pienza, a UNESCO-listed town considered to be the embodiment of a Renaissance utopia. After becoming Pope, Pius II set about transforming his birthplace into the ideal town. There are magnificent 15th-century squares and impressive palaces – many of which still sport their original sgraffito features. The episcopal palace that stands off the central square was a residence of Rodrigo Borgia, the controversial Pope Alexander VI. There’s time to explore the pedestrianised streets and imagine what life was like during the Renaissance period.
We then visit a family-run pecorino producer to delve into the fascinating world of cheese-making. Giuseppe’s family, who originally hail from Sardinia, produce many varieties of cheeses, from soft and creamy ricotta to tangy pecorino stagionato flavoured with walnut leaves. The various production processes are explained and demonstrated by Giuseppe in his expressive and inimitable style. After our tour we enjoy a light lunch comprising a selection of the fromagerie’s cheeses, perfectly paired with locally sourced wine, olive oil and Tuscan bread.
This evening, we have a farewell dinner at a local winery and reminisce about the wonderful week we’ve had of sun-baked scenery, hilltop villages and passionately prepared food.
Duration: 2 hours (3.8 miles)
Altitude gain: 590 feet
Terrain: country roads
Day 8
Transfer to the airport for your flight home.