Gently rippled hills a dozen shades of green. Cypress-lined roads leading to massive estates surrounded by seas of olive trees. Fortified hill towns of tightly huddled buildings. Pleasant hospitality and plentiful sunshine. The images are warmly familiar, as are the well-worn clichés used to describe them.

Thousands of writers have penned thousands of words about Tuscany, largely focused on marquee destinations such as Florence, Pisa and Siena. I have twice researched and written about the region for guidebooks, both times returning home with four to six pounds of souvenirs around my waist, evidence of exhaustive restaurant reviewing. And yet, it seems I've only scratched the surface. Tuscany is so densely packed with seemingly limitless abundance that, even after two thorough tours, I only cautiously declare myself an expert in its fantastical art, pulse-quickening architecture and history, its excellent restaurants, eye-popping scenic drives and life-changing agriturismi (rural farm stays). Any one of these could be the indelible experience of a lifetime that millions of travelers take home from Tuscany, and I honestly believe that no one personcould ever hope to thoroughly catalog it.

Faced with the region's daunting list of attractions - and its reputation for taking things especially slowly - visitors to Tuscany tend to confine themselves to one area and then leisurely, yet comprehensively, tour it. In the spirit of this method, I have explored the (relatively) off-the-beaten-path southeast portion of the region.

Anyone even casually versed in Tuscan wine will know the retiring hill town of Montalcino, overlooking the Orcia Valley. While it's a perfectly nice place to bulk up your calf muscles while climbing sadistically steep streets, the real attraction is the internationally coveted wine, Brunello di Montalcino, ranking among the world's best. Collectors pay hundreds of dollars for a respectable bottle at auction, the name used for a handful of mutations of the Sangiovese grape found around Montalcino, grown in select boutique vineyards. The wine is known as much for its borderline outlandish exclusivity and price as for its extraordinary quality. Rosso di Montalcino, a slightly more modest but still very respectable local red, is just as tempting.

Plenty of enoteche (wine shops) around town allow you to taste and buy Brunello. Bottles start at $28, already a staggering bargain if you've ever priced the wine in the United States, though some hunting in town shops can often win you sale-priced selections for as little as $21. There's no need to waver over these suspiciously low prices, as all Brunello is made to strict standards and any bottle will invariably be memorable. Montalcino's imposing 14th-century fortress, in addition to dominating the town from a high point at the south end, has an enoteca where you can enjoy a tasting after completing a tour of its fortified walls.

Compact Pienza won't slacken any jaws, unless you're exceptionally delighted by great-value food and accommodation, but architecture and urban-planning buffs will appreciate the town's historic center. Constructed in a mere three years between 1459 and 1462 by order of Pope Pius II, Pienza pioneered the Renaissance town blueprint that eventually spread throughout Italy and much of Europe. Designed by architect Bernardo Rossellino, who judiciously borrowed principles from his mentor Leon Battista Alberti, the centerpiece of the project is the superb Piazza Pio II and its surrounding buildings. With only limited space to work, Rossellino succeeded in increasing the sense of perspective and grandeur of Palazzo Borgia and Palazzo Piccolomini, the square's primary structures, by setting them off at angles to the cathedral, the square's final keystone.

Consecrated in August 1462, the cathedral has a Renaissance façade, done in travertine stone. The interior of the building, a blend of Gothic and Renaissance, contains five altar pieces painted by Sienese artists of the period, as wellas an outstanding marble tabernacle by the ever-prolific Rossellino. The papal bull of 1462 forbade any changes to the church, so one can revel in the thought that the interior is virtually the same now as it was for visitors in the Middle Ages. Built on unstable ground, the cathedral's most intriguing aspect is the state of collapse under the transept and apse. Unsettling cracks in the walls and floor and a worrying downward slant give the impression that the top end of the church may be breaking off. Attempts to shore up the Leaning Cathedral of Pienza have thus far failed.

Just as striking but far more physically punishing is Montepulciano, sitting on a steep, reclaimed narrow ridge of volcanic rock. The palazzo-lined climb from the visitor parking lot up Via di Gracciano nel Corso, the town's main artery, to the mesmerizing Piazza Grande will push your quadriceps to the failure point. Thankfully, there are copious places to collapse into a chair, order a glass of the highly reputed Vino Nobile and drink in the views over the Valdichiana countryside.

The namesake Vino Nobile di Montepulciano dates to 1350. It was granted the description of noble in the second half of the 18th century, and American presidents Martin Van Buren and Thomas Jefferson were among its many admirers. Some 250,000 cases of the wine are produced each year, somewhat more than one might describe as noble, but still few enough to make a bottle special.

Once you've adequately recovered from the trip up Via di Gracciano nel Corso, there's some fine exploring to be done, starting with yet another, brief climb to the top of the 13th-century Gothic Palazzo Comunale, which still functions as Montepulciano's town hall. Ona clear day, you can see as far as the Sibillini Mountains in Umbria and the Gran Sasso in Abruzzo. On the opposite side of the square is the Palazzo Contucci and its extensive wine cellar, open for visiting and sampling. Before heading back downhill, take the requisite picture in front of the beautiful 16th-century cathedral, which has an unfinished façade.

In 2003, archaeologists excavating an intact 4th-century B.C. tomb in the necropolis of Pianacce, just outside the town of Sarteano, discovered the Tomb of the Infernal Chariot.

Among the unique frescoes on the walls surrounding the alabaster sarcophagus - their colors still as bright as the day they were applied - is a demonic figure with wild flowing hair driving a chariot pulled by a pair of lions and two griffins. A three-headed snake and a huge seahorse rear up, and two male figures (perhaps a father and son as their distinct age difference shows, according to the description) have an affectionate moment. The tomb entrance has a commanding panoramic view over the Val di Chiana, very nearly worth the visit alone. Tours ($3.50), only possible on Saturdays, must be reserved through the Archaeological Civic Museum in Sarteano (Via Roma 24, tel 39 0578 26 92 61).

Six very pretty miles northeast of where the SS2 autostrada (highway) meets Buonconvento is the Abbazia di Monte Oliveto Maggiore. Construction began on the abbey in 1393, and it's still a retreat for around 40 monks today. Visitors come here for the wonderful fresco series in the Great Cloister, painted by Luca Signorelli and Il Sodoma, illustrating events in the life of St. Benedict, founder of the Benedictine order.

The backgrounds of these divergent artists are almost as engrossing as their paintings. Signorelli, reputed to be a widely respected, kind man, had previously done minor work on the Sistine Chapel and would later produce his masterpiece Resurrection of the Flesh in the Chapel of San Brizio, in Orvieto's Duomo. He started work at Monte Oliveto in 1497, producing nine frescoes.

In stark contrast, Il Sodoma, born Giovanni AntonioBazzi, was something of a character, even by artist standards. Dressing flamboyantly, keeping a Noah's ark of unusual pets, singing original ditties of dubious taste and, according to Giorgio Vasari in the book The Lives of the Artists, earning the moniker Sodoma - because he always surrounded himself with boys and beardless youths whom he loved beyond measure. He added 17 frescoes, completing the series around 1505.

If these great works haven't already blinded you with their sheer beauty, from the abbey continue driving northeast to nearby Asciano. It's one of the most stunningly scenic drives in the region, not to mention narrow, winding and not a small challenge for the driver.

It may be a stretch to describe tour-bus-bait Cortona as off-the-beaten-path, being a stand-out hilltop town in a region known for hilltop towns, but thin public transport connections keep it somewhat less hectic than its all-star neighbors to the north. Cortona started as a small Etruscan settlement in the 8th century B.C. and later become a Roman town. The beautifully messy layout is indicative of someone dumping a bucket of Etruscan town down a hillside. Though there are a few fine museums, the steep, captivating streets, some twisting off at mirthfully impossible angles, are the real attraction. These idyllic lanes have been frequently deemed film-worthy, most popularly in Under the Tuscan Sun, based on the book by Audrey Wells, and Roberto Benigni's Oscar-winning Life Is Beautiful.

Even pacing yourself during the alarming vertical gain between low-slung Piazza della Repubblica and the apex-situated Fortezza, you can easily see Cortona in a few hours. However, spending the night means enjoying streets devoid of tour bus detritus and sensational dusk and dawn views over Val de Chiana, as far as Lago di Trasimeno in Umbria.