The ancient Romans built seven major highways, two of which made a beeline south to key ports at the stiletto heel of Italy's boot. During the Middle Ages, pilgrims and Crusaders used the roads on treks to the Holy Land. These days, most travelers head to the region known as Apulia (Puglia, to Italians), only to hop a ferry bound for the Greek Isles. By scurrying straight along to sun and fun in Greece, they're missing out on the most wonderfully weird corner of Italy. Amid rolling, sun-soaked landscapes is a wild mix of architecture: cone-shaped roofs, entire towns carved into hillside caves, ancient villages all in white, and a city of baroque treasures adorned with dragons, Harpies, and other fantastical creatures. And although it may seem like the stuff of fairy tales, Apulia remains authentic and overlooked by the crowds.

Alberobello: Trulli remarkable

The Valle d'Itria is a storybook Italian landscape--stone walls dividing lush farmland into patchwork fields. Look closer and you'll see that, instead of standard farmhouses, many buildings are trulli: cylindrical homes of whitewashed limestone with conical roofs of stacked, dark-gray stones. 

Some say trulli were built that way so that peasants could pluck out a stone--and cave in the roof--whenever they saw the king's men coming, because "unfinished" structures couldn't be taxed. Others maintain that this was simply one of the easiest ways to put a roof over your head without using mortar. Whatever the case, they keep their owners cozy in the winter and cool during the baking summers.

With more than 1,400 of the beehive buildings in two separate neighborhoods, Alberobello is truly trulli central. It's also where you can try one out for the night. About a decade ago, local entrepreneur Guido Antonietta bought a few dozen abandoned trulli and installed modern kitchenettes, chunky wooden furnishings, and cast-iron bed frames. He even revived the ancient custom of painting a Paleo-Christian good-luck symbol on the roof. "I was always a little different," says Antonietta, who recalls insisting on being the lone Indian when he played cowboys and Indians as a child in the alleys of Alberobello. His company, Trullidea, rents the one-room homes for $95 to $112 per night, less than what some nearby hotels charge.

So what do you do in your trullo? First, open the shutters on the deep-set window to let some light in on the stone floors. Like the outside walls, the interiors are slathered in whitewash, even on the inside of the stone roof, though that's usually blocked off by a ceiling of wooden planks. Bathrooms and kitchens are tiny but usable, and shops are never more than a few blocks away.

Then take a cue from the locals. Up and down Alberobello's steep streets, you'll see women stationed in doorways, sitting in cane-bottom chairs. They keep their hands busy--shelling peas, mending dresses, crafting toy trulli for their sons' souvenir shops--while chatting with their neighbors, each perched in her own doorway. (Italian men, on the other hand, traditionally congregate in public places--at the local bar, on a roadside bench, or in the piazza.) Follow the ladies' lead and drag a cane-bottom chair into your own doorway. Your only chore is to while away the afternoon, soaking up the sun and maybe reading.

Although trulli are still sprinkled throughout the Valle d'Itria, the majority of architecture outside Alberobello is modern in a boring way. An exception is the area along an unnamed back road linking Alberobello with the town of Martina Franca. It's frozen in the Apulia of ages past, blanketed with olive groves, vineyards, and hundreds of trulli. The road is a devil to find, though: Do not follow the signs toward Martina Franca from Alberobello's center. Instead, follow signs to Locorotondo, and, as you leave Alberobello behind, look on the right for a white sign pointing to Agriturismo Greek Park. That's the road. It's narrow, fenced in by stone walls--scary when you meet the rare oncoming car--and it cuts right through the hidden heart of the Valle d'Itria.

At some point, do continue down the main road to Locorotondo, a hill town of concentric streets lined with whitewashed buildings. Locorotondo's nickname is "the balcony on the Valle d'Itria" because of its stunning valley views. Within Italy, Locorotondo is even better known for its wine. The region of Apulia is Italy's most prolific wine producer, churning out 17 percent of the national total. For centuries, it was just the grapes that interested the world's wine industries. Turin imported them to make vermouth, and France would sneak them into their presses during bad harvest years. But Apulian wine now trades on its own merits, getting press in culinary magazines and showing up in U.S. wine stores. Robust, structured reds, such as Primitivo and Salice Salentino, are as rich and complex as anything you'll find in Tuscany, but they start at around $7 per bottle, a fraction of what you pay for wine of similar quality in Florence. A standard table wine in Apulia costs less than $3. For free tastings (and cheap bottles), head to Locorotondo's Cantina Sociale, a wine cooperative made up of more than 1,000 local vintners.

The raw earthiness of even Apulia's younger reds partners perfectly with the strong flavors of local cooking, where stewed meats are a staple. In Locorotondo, try Giovanni Loparco's homey Trattoria Centro Storico, the locals' preferred lunch spot, kept cool by thick stone walls (important when southern Italy's powerful sun is out). Try the house pennette, a quill-shaped pasta in a hearty tomato sauce spiked with hot peppers, onions, and chunks of ham, or Giovanni's signature portafoglio--a "wallet" of lamb chops stuffed with cheese, parsley, and wild herbs.

For an even more memorable meal, drive 15 miles east, up a 715-foot hill, to Ostuni. Known as the White City, Ostuni is a spiral of buildings layered with so much whitewash that they look sculpted from meringue. Inside one is Osteria del Tempo Perso. The front room is decorated with watercolors of Ostuni scenes, dozens of old farm tools, and, hanging in an alcove, an antique bicycle. Deeper inside, past pendulums of cured meats and garlands of garlic and red peppers, is a candlelit dining room in a cave that was carved out of bedrock 500 years ago. Stacks of colorful fruits and vegetables surround a central column; the chef occasionally pops out of the kitchen to pluck a few for his recipes. Sit at one of the thick wooden tables and, even before you receive a menu, the waiter drops off a dozen tiny plates laden with antipasti: stuffed mushroom caps and frittata wedges, falafel and steamed tripe, roasted vegetables in olive oil, and cheeses stuffed with other cheeses. For the main courses, try Apulia's Frisbee-shaped orecchiette pasta under a tomato sauce speckled with salty cacioricotta cheese or topped with bitter turnip greens laced with spicy pepperoncini. If there's still room, go for the arrosto misto, a platter of roasted sausage, lamb, and liver.

Work off the feast by wandering through the White City's maze of alleys, which are too narrow even for Italy's minuscule cars. Peek between buildings for views over terraced vineyards and olive groves to the Adriatic Sea, less than four miles away.