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Chianti, Val d'Orcia & Co. – The Tuscan Hills

The Most Beautiful Countryside In The World

The sound of cicadas in the hot Tuscan afternoons, the cypress trees that snake along the country lanes, sweets horizons of vineyards and charming medieval villages. For scenic beauty and artistic richness, the Sienese countryside is undoubtedly one of the most beautiful spots in the world. Six outstanding valleys compose the province of Siena: Chianti, Crete Senesi, Val d’Orcia, Val d’Elsa, Val di Merse and Val di Chiana. Each valley contains unique treasures, both naturalistic and cultural. Every valley alone is worth the trip.

Chianti does not need any introduction. It is home to one of the finest red wines in the world, Chianti Classico, marked by the historic symbol of the black rooster. Not to mention the Val d’Orcia, one of the most beautiful countryside in the world. Listed among UNESCO World Heritage sites, this valley has inspired Renaissance painters and artists from around the world. Tuscany has even its own desert: the Crete Senesi, famous for the lunar landscapes and spectacular ravines, endless meadows and rarefied atmosphere.

And then the Val d’Elsa, known for its glassware, the Val di Chiana, where are grown the prized Chianina cows, and the beautiful Val di Merse, rich in natural parks and off the beaten track. Among the gentle slopes of these six valleys are art towns of the caliber of Pienza, San Gimignano, Montalcino and Bagno Vignoni, not to mention the city of Siena, the abbeys and castles. Last but not least, the wine and food traditions of these ancient lands will irremediably pamper the lucky traveller. In summary, this is the trip of a lifetime.

Geography

The Tuscan hills are composed of fertile and mild landscapes that man has shaped over the centuries. Local valleys follow the course of several rivers that make the earth fertile. The two highest mountains are Mount Amiata, an extinct volcano (1738 meters), and Mount Cetona (1148 meters). Chianti has rather high hills, while the largest plain is located in the Val di Chiana.

Moving Around

Car, motorcycle, bicycle, train or bus: this is a place where the movements are part of the journey. Drive along the Via Chiantigiana SR222, designed on the Chianti hills, that you can also travel by bike. Climb on the steam train Treno Natura to visit the Crete Senesi or get lost in the back streets of Val d’Orcia. Always remember, the watchword is: move slowly.

Nature Wonders

In addition to its famous vine-covered hills, the Sienese countryside boasts 11 nature reserves that protect about 8,000 hectares of land, including hills, woods and rivers. These diverse and marvelous reserves are home to a rich fauna of birds, mammals and rodents, and are crossed by trails for hiking, horseback riding and paths for bikers. Far, far away from the rush of city life.

Cultural Marvels

It is impossible to describe in a few words the artistic and cultural wealth of this region of Tuscany. Perhaps one could say that, if there is one place in the world with the highest concentration of art treasures, this place is the Tuscan hills. The four cities listed among UNESCO World Heritage Sites – Florence, Siena, Pienza and San Gimignano – are just a glimpse of this splendor.

Top 5 Things To Do On The Tuscan Hills

THE TUSCAN VALLEYS

Chianti

Famous throughout the world for its idyllic landscapes and its excellent wines, Chianti is a small mountainous and hilly chain located between the provinces of Siena, Florence and Arezzo. 70,000 hectares of this land are destined to the production of Chianti Classico, an ancient wine produced since the time of the Etruscans. Go through the road Chiantigiana (SR222) which meanders between cypress trees and rolling hills. Visit the small medieval hamlets of the region and find out your favorite wineries. Do not miss a wine tasting tour, the most important activity of the area. Nature lovers can take a walk in the beautiful woods of cypress trees of the Nature Reserve Bosco di Sant’Agnese.

Val d’Orcia

According to UNESCO, which in 2004 has included this outstanding valley among the World Heritage sites, ‘the Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing pictures’. Here art and nature blend together. Crossed by the river Orcia, the valley runs between Siena and Grosseto, at the foot of Mount Amiata. From this fertile land come the red wines Brunello di Montalcino and Nobile di Montepulciano, as well as dozens of other local products. For a postcard picture do not miss the famous group of cypresses of the chapel of Madonna di Vitaleta, near San Quirico d’Orcia.

Crete Senesi

To the south-east of Siena, the Crete Senesi is the desert of Tuscany. A lunar landscape of gullies which owes its name to the blue-gray clay in the soil. Here you will not see the vineyards and olive groves that characterize the Tuscany hills. The Crete Senesi bare fields stretch as far as the eye, crossed by rows of cypress trees and some isolated cottage. Drive along the beautiful road from Siena to Asciano, visit the Accona Desert and the Lucciola Bella Nature Reserve, which  is located in the Val d’Orcia but has characteristics typical of the Crete Senesi. Admire the ‘gance’, warehouses and barns of medieval origin, and taste the white truffle, a typical product of the region.

Val d’Elsa

The valley of the river Elsa stretches between the provinces of Siena and Florence, on the border with Chianti. Characterized by low hills and and splendid art towns, the Val d’Elsa is known since the Middle Ages for its glassware and saffron. It is crossed by the Francigena road and boasts the wonderful Nature Reserve Castelvecchio Val d’Elsa, a few kilometers from San Gimignano. The reserve includes 734 hectares of very diversified woods with hanging bridges and historic ruins, inhabited by woodpeckers, foxes, squirrels and deer. A dip in the green. Do not miss the waterfall of Diborrato and the Fluvial Park of the Val d’Elsa, where you’ll find a well-equipped 4 km track.

Val di Chiana

In Italian Journey Goethe wrote that it was not possible to see more beautiful fields than those of the Val di Chiana. In between Tuscany and Umbria, this alluvial valley is the homeland of the famous Chianina cattle breed renowned for its meat (do not miss a steak alla Fiorentina!). Walk by foot or by bike along the Sentiero della Bonifica, 62 km in the plains along the river Canale Maestro, the biggest of Val di Chiana. Trekking lovers can explore Mount Cetona (1148 meters), on the border with Val d’Orcia, and bird watchers should not miss a visit to the Lake Montepulciano Natural Reserve, one of the most important wetlands in central Italy. Here you can witness the show of migrating birds.

Val di Merse

The Val di Merse is an intimate and unknown Tuscany, a secret hideaway off the beaten track. Located between the Crete Senesi and the Maremma, the valley is created by the river Elsa and today is almost entirely a nature reserve. The territory consists of high hills, forests and agricultural areas. Here nature lovers can explore on foot, by bike or on horseback the Alto Merse Nature Reserve, covered with deciduous forests, where beautiful waterfalls enrich the landscape. Do not miss a walk in the parks of Montieri or in the woodlands of Radicondoli and Sovicille. Visit the splendid castle of Murlo, enjoy the ancient hot springs of Petriolo or arrange a grand tour of the valley by bicycle.

CULTURAL MARVELS

Chianti Hamlets

Famous for its vineyards, the Chianti region also boasts beautiful historic towns. Greve in Chianti is considered the gateway to the region. Visit the ravishing triangular square of the hamlet and make a stop at the Wine Museum. Near Greve is the medieval castle of Montefioralle, not to be missed. Further along there are Panzano, which offers stunning views over the Tuscan hills, and Castellina in Chianti, which has Etruscan origin. Here you can visit the Etruscan tombs of Monte Calvario, the most important archaeological site of Chianti. In Radda in Chianti we recommend a visit to the wineries that produce wine as it used to. Explore also Gaiole in Chianti and the unexpected castles of the region.

Val d’Orcia Hamlets

The Val d’Orcia boasts dozens of art treasures. Pienza, the ideal Renaissance town, perched on top of a panoramic hill, a UNESCO World Heritage site. San Quirico d’Orcia and Bagno Vignoni, the only hamlet in the world to have, instead of the square, a large thermal water basin. Montalcino, Brunello wine homeland, intact since the sixteenth century. The Abbey of Sant’Antimo, one of the best examples of medieval monastic architecture in Italy, where you can still listen to the Gregorian chants during mass. Finally the castle of Radicofani, the village of Castiglione d’Orcia and Rocca d’Orcia tower, where you can admire one of the most beautiful views of the valley.

Val d’Elsa Hamlets

The Val d’Elsa is unmatched for artistic richness. Discover the outstanding hamlet of San Gimignano with its 72 medieval towers, another UNESCO World Heritage site. Its silhouette towering over the countryside, the central square and narrow streets perfectly preserved are unforgettable. Go on to Colle Val d’Elsa that since ‘500 became famous throughout the world for the production of crystal (visit the Museum of Crystal). Do not miss the beautiful Monteriggioni, one of the most famous walled towns in Italy, famous throughout the world, with its wall of 570 meters interspersed with 15 towers built by the Sienese in 1213-1219. Admire the antique churches and noble residences that make the region unique.

Val di Chiana Hamlets

First of all Montepulciano, the pearl of the ‘500, famous for its red wine Nobile di Montepulciano, made resplendent by the Medici family in the sixteenth century. This hamlet on the border with the Val d’Orcia offers unforgettable views. Do not miss the central square, the Temple of San Biagio and a visit to one of many wineries. And then the fortified village of Cortona, a panoramic terrace overlooking the Val di Chiana, Cetona, an aristocratic and rural hamlet at the foot of Mount Cetona, and the spa hamlets of San Casciano dei Bagni and Chianciano Terme. If you are in May in Val di Chiana, do not miss the Maggiolata di Lucignano, the best spring festival of Tuscany.

San Galgano Abbey

This Cistercian abbey built in 1218 has the structure of a majestic Latin cross with three naves, 72 meters long, 21 wide, with the outer walls still intact, but without a roof. The visual impact is impressive. Nearby is the hermitage Rotonda di Montesiepi, even older then the abbey. Here you can admire the sword in the stone of San Galgano, an image that immediately brings to mind Excalibur, the legendary sword of King Arthur. The sword dates back to 1147 and legend has it that the knight Galgano plunged it into the rock as a sign of his renunciation of worldly life. With this vote, the Knight became the first hermit and then a saint. The Abbey of San Galgano is situated in the Merse Valley, in the town of Chiusino.

Chianti Sculpture Park

The sculpture park of Chianti is a permanent outdoor exhibition of sculptures and installations located in Pievasciata, town of Castelnuovo Berardenga, 10 km north of Siena. Opened in 2004, the park covers 13 hectares of pristine forest of oak trees, where 26 major installations by artists from all five continents are scattered. The visit is perfect also for kids and takes place along a path of 1 km that can be covered in a couple of hours. Among the most significant works the imposing ‘Energy’ by the Greek Costas Varotsos, ‘The Leapfrog’ by Dominic Benhura of the African tribe of the Shona, and ‘The Labyrinth’, interactive sculpture by the English Jeff Saward.

TUSCAN HILLS STARRED RESTAURANTS

Favorites

Great Locations

Hotel Restaurants

  • Arnolfo **

    Run by two brothers, friendly atmosphere, sophisticated and impeccable cuisine. 2 Michelin stars.

    Via XX Settembre 50/52 – Colle Val d’Elsa
    GPS: 43.420931, 11.116623
    Phone: (+39) 0577 920549

  • La Bottega del 30 *

    In a charming little hamlet, outside terrace on the Tuscan hills, delicious cuisine. 1 Michelin star.

    Via S. Caterina 2, loc. Villa a Sesta – Castelnuovo Berardenga
    GPS: 43.384903, 11.480302
    Phone: (+39) 0577 359226

  • Il Colombaio *

    For those who think that here you can not eat good fish. Charming location with panoramic terrace on the surrounding hills. 1 Michelin star.

    S.P. 27 in Cavallano – Casole d’Elsa
    GPS: 43.420911, 11.116645
    Phone: (+39) 0577 949002 

  • Meo Modo *

    Extraordinary setting, a romantic porch overlooking the garden and the Tuscan hills, delicious cuisine. 1 Michelin star.

    Località Palazzetto 110 – Chiusdino
    GPS: 43.143373, 11.127822
    Phone: (+39) 0577 751222

  • Osteria di Passignano *

    Beside the abbey, in the ancient cellars of the Marchesi Antinori, modern style cuisine with solid roots in tradition. 1 Michelin star.

    Via Passignano 33 – Badia a Passignano
    GPS: 43.580282, 11.249350
    Phone: (+39) 055 8071278

  • Castello di Fighine *

    A fairy-tale medieval castle with beautiful views and a romantic terrace covered with wisteria. Fresh cuisine. 1 Michelin star.

    Loc. San Casciano dei Bagni – San Casciano dei Bagni
    GPS: 42.886482, 11.915742
    Phone: (+39) 057 856158 

  • I Salotti *

    The hotel restaurant of Villa Patriarca proposes a refined atmosphere, a few tables, just 2 tasting menus. 1 Michelin star.

    Loc. Querce al Pino, SS 146 – Chiusi
    GPS: 43.018768, 11.903874
    Phone: (+39) 057 8274407

  • Il Falconiere *

    The hotel restaurant Il Falconiere: beautiful panoramic terrace and a solar kitchen, typically Tuscan. 1 Michelin star.

    Località San Martino – Cortona
    GPS: 43.290299, 11.970895
    Phone: (+39) 057 5612679

  • La Torre *

    The stylish hotel restaurant La Torre, high-quality cuisine. 1 Michelin star.

    Strada Spicciano 7 – Tavernalle Val di Pesa
    GPS: 43.551484, 11.187515
    Phone: (+39) 055 806470

Found villas: