Ever since the Etruscans made Tuscany their home, many have fallen under its spell. Perhaps it’s the ethereal light on the endless sea of vineyard-clad hills, or the enviable climate in which so much seems to thrive. It could be the infectious passion for good food and wine, but maybe it’s the centuries of heritage that keep travellers captivated. During the great Renaissance period, Tuscany attracted some of the most admired architects, painters and sculptors of the time. As such, art in Tuscany is some of the most remarkable in Europe, be it on proud display in grandiose squares or closely guarded in galleries, museums and churches.
Our guided walking tours let us fully appreciate the magical landscapes. We explore the UNESCO-listed Val d’Orcia, the embodiment of Tuscan countryside and many an artist’s dream. Green vineyards, golden barley fields and silvery olive groves parade in an explosion of colour across hills that rise and fall hypnotically on a canvas of chalk plains.
We’ll follow rustic paths lined by sculptural cypresses and discover medieval towns and villages untouched by time, such as Pienza, San Quirico and Monticchiello. We go inside the vast defensive walls of majestic Siena to soak up its extraordinary ambience – it is made up of a collection of small parishes, each with its own unique identity. The city also has a beautiful square, Piazza del Campo, with a soaring campanile.
South of Siena, the Crete Senesi surprises with its dune-like hillocks, creating an otherworldly atmosphere. The clay-rich soil changes colours, depending on the season and time of day, from stark white and grey to a lovely orange at sunset.
We cross into neighbouring Umbria, the green heart of Italy, and visit the magnificent university city of Perugia. One of the legendary Etruscan cities, it oozes history in every corner. For a taste of the ‘sea’, we visit the lovely town of Passignano on Lake Trasimeno, affectionately called the Sea of Umbria by locals of this landlocked region.
Far removed from pizza and pasta, Tuscany has a gastronomic culture that shows the central importance of food and drink in life. The extra virgin olive oil produced here is world-famous for its strong and fruity flavour. Then there’s pecorino, the buttery sheep’s milk cheese, considered by many to be the best in Tuscany. It pairs perfectly with the famous wines of Montepulciano – why not personalise your holiday with a visit here?
Our wonderful tour combines all the ingredients for an unforgettable taste of life ‘under the Tuscan sun’: picture-postcard scenery, architectural jewels, cultural highlights and foodie favourites – and delightful walks to discover them all.
You will be met by a member of the Riviera Travel team before your flight to Rome. On arrival we transfer by coach to the three-star superior Grand Hotel Excelsior, located in the hillside spa town of Chianciano Terme in the splendid Tuscan countryside. Settle in before joining your tour manager this evening for an informal welcome drinks reception, followed by a typical Tuscan three-course dinner at the hotel restaurant.
This morning we drive to the medieval walled town of San Quirico d’Orcia in the heart of Val d’Orcia, a beautiful painting come to life. Considered the quintessential Tuscan landscape, the valley has inspired many artists and is recognised by UNESCO as an icon of the Renaissance. Fortified villages and majestic abbeys crown the smooth hills, blanketed with a medley of vineyards, orchards and olive groves.
To discover the area, we begin our gentle walk in San Quirico d’Orcia and follow in the footsteps of pilgrims along part of the famous Via Francigena route, which connected Canterbury cathedral with Rome in the Middle Ages. Little seems to have changed since the 10th century when the route was described by Sigeric the Serious, Archbishop of Canterbury. The surrounding hills are dotted with rustic villages, farms and vineyards connected by cypress-lined tracks and footpaths.
We arrive in Bagno Vignoni, which bears the appearance of a typical Tuscan village, but in place of a traditional main square is a large pool filled with water from the village’s thermal springs. While you can’t take a dip in the main square, you can soothe your feet in the rejuvenating warm spring waters as they are channelled through the village, or the more adventurous can take a dip in the hot springs at the Parco dei Mulini for a bit of well-deserved pampering at the end of a wonderful walk.
Duration: 1.5 hours (3 miles)
Altitude gain: 164 feet
Terrain: country roads
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.
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
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.
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.
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
Transfer to the airport for your flight home.
The price of this holiday is per person based on sole occupancy of a twin/double room. The price includes:
All transfer times listed here are approximate, and dependent on traffic. If you have a question regarding transfer times please don't hesitate to contact us.
|Airport||Hotel location||Transfer time|
|Rome||Chianciano Terme||2 hrs 45 mins|
UK Citizens do not require a visa to enter Italy however must have a valid passport. For the most up-to-date passport and visa information visit https://www.gov.uk/foreign-travel-advice/italy/entry-requirements
We are unable to accept responsibility if you are unable to travel because you have not complied with any passport/entry/immigration requirements.
Just returned home from our River Cruise. The cruise ,Ship, Staff ,food and tours are first class. Our experience was faultless ,well done Riviera. Tracy Robinson....
We've just returned from a week based in Sorrrento. Our tour manager said, 'It's not a holiday, it's a tour'! She was right - lots of early mornings, and long days, but what days! It was the most amazing experience - all the ex...