Central Tuscany is the bit that looks like it's supposed to -- the wondrous region of a million postcards and wall-calendars, where corrugated, vine-crowned hills roll their way to a hazy horizon. The principal "city" of the area is Siena, a great banking and textile rival of Florence in the Middle Ages that has preserved dozens of noble palaces and art-filled churches, none greater than its Gothic-Romanesque Duomo. Its museums are filled with a distinctive and decorative style of painting quite outside the Florentine tradition. Between there and Florence lies one of the region's most picturesque parts: the castle-topped hills and Arcadian vineyards of the Chianti, Tuscany's internationally famous winelands.

Siena is also the epicenter of hill-town territory, a landscape of small mountains and river-fed valleys watched over by stony medieval towns perched on the taller peaks. West of the city, in bucolic, idyllic countryside, hide two of the more famous and visited towns: San Gimignano still sprouts more than a dozen medieval towers, and Volterra is an ancient Etruscan center and modern workshop of alabaster artisans.

The Chianti

You can find many people's idea of earthly paradise in the 167 sq. km (64 sq. miles) 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 people come -- the tall, closely gathered hills are capped by ancient cities and medieval castles, and the stream-fed valleys are dotted with jovial winemaking and 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 (9,884 acres) are blanketed with vines.

This is the world's definitive wine region, in both history and spirit; these hills have been an oenological center for several thousand years. Indeed, 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 used by hundreds of poor-quality, vino-producing hacks, both within the region and from far-flung areas, diminishing the reputation of the wine. To fight against this, Greve and Castelnuovo Berardenga joined the original Lega cities and formed the Consorzio del Gallo Nero in 1924, reviving the black rooster as their seal. The consorzio (still active -- their members produce about 80% of the Chianti Classico that's 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 Italy. Today, of the 100 sq. km (39 sq. miles) of vineyards in the hills between Florence and Siena, some 6,972 hectares (17,228 acres) are devoted to the grapes that will eventually become Chianti Classico and carry the seal of the black rooster.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.