BICYCLE TOUR AT A GLANCE

Dates: 2007
Trip Price: $3,195/person
Duration 6 Days
Level: Advanced Moderate to Challenging
Accomodation Deluxe Inns & Villas
HighlightsTuscany, Pienza, Siena, Chianti, Montepulciano, Montalcino

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Tuscany History

Val d'Orcia

Today Val d'Orcia is peripheral, a land fresh and unspoiled where the character of its agricultural economy and the persistence of the inhabitants to work the earth and the natural materials found in the area, have safeguarded the relationship between man and the environment.  This valley is not only a place full of poetry and naturally happy people. It is a valley which contributed to handing down history and human relationship which has determined the quality of an area which was traversed by the roads of ancient Rome - The Francigena. All the events which developed along this highway and the adjacent hills, created a landscape which fascinated the great Sienese painters of the Renaissance, the European travelers of the "grand tour", the romantic writers of England, Germany and France, and which still charm us to this day. The scenery of the Val d'Orcia, which begins with a symmetry of natural harmony with its soft rolling hills, changes into the majestic grandeur of the Amiata, a mountain abounding with springs of crystal clear water and luxuriant vegetation. The colors of dry clay and golden earth, share the hills; dark green moss and undergrowth cover the base of rocky crags and old farm houses; the gentle colors found in the orderly lines of vineyards mix with the silver grey of the olive groves. The solitude, the empty spaces, the light, the views, conjure up a sense of pleasure, delight and even loneliness difficult to define. The Val d'Orcia is a landscape of never-ending hills, interspersed with torrents, ravines, rugged outcrops, river banks which intertwine until they are lost in the ash color of the distant Crete. The Francigena, winding among this natural but hostile beauty throughout the centuries, has contributed towards the growth of the small centres and the pride of an ancient people, accustomed to sharing the dreams, arrogance and the Utopia pf powerful and famous men. The farming community of the Val d'Orcia has never surrendered to progress, it has always welcomed travelers and pilgrims and always made them welcome.

Pienza

In the midst of the rolling farmland of Tuscany's Val d'Orcia, on a tiny bump of a hill, the village of Pienza sits as a testament to one man's ambition and ego. At the height of the 15th-century Renaissance, humanist Pope Pius II, with the help of architect Bernardo Rossellino, converted the tiny village in which he had been born into the ideal Renaissance city. The "city" began and ended with the new central square and its buildings -- the plan to cover the surrounding area with a grid of streets never materialized. The village of Pienza, however, retains its remarkable city-size piazza, one of the grandest achievements of Renaissance architecture and the only intact example of a city-planning scheme from the era. Director Franco Zeffirelli was so taken by the village's look he dethroned Verona as the city of the Montagues and Capulets and filmed his Romeo and Juliet in Pienza. Pienza was also used in the Oscar-winning epic The English Patient.

But for all Pius's dreams, Pienza never became more than a village. Today, its 2,500 inhabitants put up with the stream of day-trippers with good humor, lots of craft stands, and a surfeit of health-food stores. The main drag, Corso Rossellino, goes in one end of town and out the other in less than 2 minutes at a stroll. There are a handful of spacious side streets within Pienza's proud little walls, and modest new developments surround the burg on three sides (the 4th is saved for a view). Pienza will take no more than half a day in your schedule, time enough to admire the palaces, Sienese art collection, and Duomo at the town's perfect core; nibble on the famous goat cheeses and honey; and take a short walk to the odd, isolated medieval churches in the countryside outside the walls.

Montepulciano

The biggest and highest of southern Tuscany's hill towns, steeply graded Montepulciano, with its medieval alleyways and plethora of Renaissance palaces and churches, has just enough city feel and tourist infrastructure to make it one of the best bases for visiting the region. The fields around the town produce a violet-scented, orange-speckled ruby wine called Vino Nobile di Montepulciano. This area has been known since at least the 8th century for its superior wine, and in the 17th century, when Francesco Redi wrote his vino-praising poem, Bacchus in Tuscany, he described the Noble Wine of Montepulciano as "The King of all wines." Vino Nobile is known as Tuscany's number-two red because it's slightly less beefy than Montalcino's Brunello. But for my money, its high quality and more mellow character make it a better all-around wine, good to age and save for special occasions but also to toss back with dinner or on a picnic.

The locals call themselves Poliziani after the Roman name for the town, and Poliziano is also the name the local classical scholar/humanist Angelo Ambrogini took when he went to Florence to hold discourses with Lorenzo de' Medici, tutor Lorenzo's sons, and write some of the most finely crafted Renaissance poetry of the era -- some say his Stanze per la Giostra inspired Botticelli's mythological paintings, like the Birth of Venus and Allegory of Spring.

Montalcino

Montalcino presents a mighty image on the approach from the valley -- a walled town set very high on a tall hill with the spires of medieval buildings sprouting from the middle and a glowering fortress at one end. Up close, the town becomes a much smaller, meeker place, but the precipitous medieval alleyways and stone buildings make it a day-trip delight, and the views of the valleys from which you just ascended are magnificent from this height.

Paleolithic tribes and the Etruscans set up camp here, but it wasn't until the Roman era that a permanent settlement formed. By the Middle Ages, Montalcino was a bustling town and a defensive center for the surrounding farming community. Although it divided itself into four minuscule neighborhood contrade after the Sienese model, Montalcino was initially allied to Florence and at odds with its northerly neighbor Siena. After several skirmishes, though, the Sienese took over Montalcino in the 13th century. By 1462, the town had grown large enough to be declared a city, and in 1555 its now-cozy relations with Siena led it to harbor the 700 Sienese families who refused to submit to the Medici when Florence defeated Siena. The exiles set up the defiant "Republic of Siena at Montalcino," which lasted 4 years until the Medici grand dukes finally laid their hands on both the Sienese and Montalcino through treaty. Montalcino's loyalty is honored to this day -- their standard-bearer rides in pride of place at the front of Siena's annual pre-Palio parade.

Montalcino's Medici-induced slide into obscurity began to turn around in the 1960s, when the world discovered that the sangiovese grosso grapes -- known as "Brunello" to the locals, who had been quietly experimenting with them for about a century -- made one of the finest red wines in all Italy. Today, with an annual production of more than 3.5 million bottles of Brunello di Montalcino -- and 3 million of its lighter-weight cousin Rosso di Montalcino -- Montalcino has become a rather well-to-do town. Also, don't miss the white dessert wine called Moscadello or the fine honey.

Chianti

Siena, a great banking and textile rival of Florence in the Middle Ages, slumbered through the Renaissance. As a result, it has preserved dozens of Gothic palaces and churches, and its museums are filled with a distinctive and decorative style of painting. Many visitors zip south from Florence to Siena on the train or along the autostrada and end up missing one of Tuscany's most picturesque regions: the castle-topped hills and Arcadian vineyards of the Chianti, Italy's most famous wine district.

Siena is also the center of hill town territory, a landscape of small mountains and river-fed valleys watched over by stony medieval towns perched on the taller peaks. (Those south of Siena are covered in chapter 8.) West of the city, in some of the tallest mountains of central Tuscany, hide two of the more famous hill towns: San Gimignano still sprouts more than a dozen medieval towers, and Volterra is an ancient Etruscan center and modern workshop of alabaster artisans. Nearby, but seldom visited, Massa Marittima makes a great excursion off the beaten path into a city from the Dark Ages.

Wine Tasting in the Chianti

You can find many people's idea of earthly paradise in the 167 sq. km (65 sq. miles) plot of land between Florence and Siena, known as the Chianti. In fact, the British have such a history of buying up old farmhouses and settling here it's often referred to as Chiantishire. It isn't hard to see why they come -- the tall, closely gathered hills are capped by ancient cities and medieval castles, and the stream-fed valleys are dotted with expanding market towns. All is often shrouded in a light mist that renders the blue-gray distance inscrutable and cloaks the hills in a mysterious rural magic. Many of the rolling slopes are planted with olive groves that shimmer dark green and dusty silver, but some 4,000 hectares (10,000 acres) are blanketed with marching vines. The grapes that grow from these gnarled woody question marks form the primary capital in the region's bacchanalian economy.

 Chianti Classico

This is the world's definitive wine region, in both history and spirit; these hills have been an enological center for several thousand years. In fact, one local grape, the Canaiolo nero -- one of the varietals that traditionally goes into Chianti Classico -- was known to the ancients as the "Etruscan grape." The name Chianti, probably derived from that of the local noble Etruscan family Clantes, has been used to describe the hills between Florence and Siena for centuries, but it wasn't until the mid-13th century that Florence created the Lega del Chianti to unite the region's three most important centers -- Castellina, Radda, and Gaiole -- which chose the black rooster as their symbol. By 1404 the red wine long produced here was being called chianti as well, and in 1716 a grand ducal decree defined the boundaries of the Chianti and laid down general rules for its wine production, making it the world's first officially designated wine-producing area. In the 19th century, one vintner, the "Iron Baron" Ricasoli, experimented with varietals using the sangiovese grape as his base. Working off centuries of refinement, he eventually came up with the perfect balance of grapes that became the unofficial standard for all chianti.

Soon the title "chianti" was being taken in vain by hundreds of poor-quality, vino-producing hacks, both within the region and from areas far flung, and the international reputation of the wine was besmirched. To fight against this, Greve and Castelnuovo Berardenga joined the original Lega cities and formed the Consorzio del Gallo Nero in 1924, reviving the old black rooster as their seal. The consorzio (still active -- their members produce about 80% of the Chianti Classico bottled) pressed for laws regulating the quality of chianti wines and restricting the Chianti Classico name to their production zone. When Italy devised its DOC and DOCG laws in the 1960s, chianti was one of the first to be defined as DOCG, guaranteeing its quality as one of the top wines in the country. Today, of the 100 sq. km (39 sq. miles.) of vineyards in the hills between Florence and Siena, some 6,972 hectares (17,430 acres) are devoted to the grapes that will eventually become Chianti Classico and carry the seal of the black rooster