Road Trip: Coast to Coast in Puglia, Italy

A picture-perfect circuit through seaside towns, prehistoric dwellings and more

Visitors seeking to explore Italy’s sun-drenched Puglia region are spoiled immediately upon arrival. With Adriatic to the East and the Ionian to the West, a less-than-one-hour driving distance between the two coasts means the cliff-hugging seaside towns, ancient archeological sites, and everything in between can be efficiently explored by car. For being the heel to Italy’s boot, Puglia is relatively flat, hosting sprawling olive groves that dominate the landscape and the country’s olive oil production. And while its dreamy coastal towns are unmissable, Puglia’s interior holds treasures you won’t see anywhere else in the world. After picking up our Fiat 500 Cabrio from the Bari International Airport and rolling the top down, we devised a counter-clockwise circuit to hit the area’s most enchanting sites that include a network of caves inhabited since the Paleolithic era, swoon-worthy hotels, and one of the world’s most photogenic beaches.

Sassi di Matera, Matera

Technically the “City of Caves” isn’t in Puglia—it’s located just across the region’s border in neighboring Basilicata—but Matera’s status as one of the most fascinating places anywhere earned its place as this road trip’s first stop. As 2019’s European Capital of Culture, Matera has metamorphosed from being “the shame of Italy,” poor and disease-ridden, into one of the country’s straight-up coolest destinations. Centered around the Sassi, an ancient area made up of caves inhabited for over 7,000 years, Matera is the world’s third-oldest continuously inhabited city. Wandering the mostly-pedestrian streets that descend into the crater-like district is a borderline spiritual experience, where the natural caves have been converted into shops, restaurants, and hotels (like the outstanding Sextantio Le Grotte Della Civita). No matter how you spend your day in Matera, end with cocktails at the ultra-creative Area 8.

Metaponto Archeology Museum and the Tavole Palatine, Metaponto

A trip to Italy remains incomplete without at least one museum stop. Heading south towards Puglia’s Ionian coast, we stopped at the Metaponto Archeology Museum to view its collection of relics from the area of Metaponto, an ancient Greek colony. It’s a small, little-known museum guaranteed always to be be uncrowded. That doesn’t mean its collection isn’t impressive: wonderfully preserved painted ceramics, intricate gold jewelry, and diverse weaponry from both the Greeks and Romans, and the indigenous population prior to colonization, are on display. About 10 minutes away by car, right off a busy highway, is the Tavole Palatine, a Greek temple dedicated to the goddess Hera from the 6th century BC.

Masseria Potenti, Manduria

Masseria Potenti is an undeniably romantic converted farmhouse surrounded by olive groves outside the town of Manduria. With whitewashed exteriors, bohemian furniture, dried flowers swaying from the ceiling, and walls of overgrown cacti framing pastel doors, it’s incredibly photogenic. A hotel and popular wedding venue, there are 17 rooms and suites, a pool, and resident dogs that meander through the property. Potenti’s fantastic restaurant is well-known throughout the region, attracting diners to taste locally grown produce, fresh-caught seafood, and a pastry collection that’s unbelievable. The Masseria was created by Milan-based Maria Grazia Di Lauro and husband as a passion project to return to her family’s Puglian roots, and it’s a success at showcasing their organic hospitality and irresistible joie de vivre.

Don Totu, Dimora Storica, San Cassiano

Perhaps the sole reason to visit the tiny village of San Cassiano, in the Salento area of southern Puglia, is to stay at Don Totu. A dimora storica, or historical residence, Don Totu is an outstanding boutique hotel situated within an understated, yet regal compound that consists of a restored former palazzo and a tasteful modern expansion. There are just six guest rooms here—all massive and stone-walled, ensuring an intimate experience. The common areas are impeccably elegant, yet comfortable. The entire property encourages guests to have a “just help yourself” mindset, from the kitchen stocked with pastries and juices, to the fragrant garden where you can pick your own strawberries and figs. The pool area is spacious and divine, with a Hockney-inspired “quiet room” that hosts original artwork and modern décor from Miami and exotic elsewheres. Aperitivo hour is every day from 6PM, so a perfect negroni is reliably close by.

Lecce Centro Storico, Lecce

“The Florence of the South” is filled with so much baroque architectural splendor, the local style has its own name: barocco Leccese. The majority of its historical center is constructed with unique Lecce stones, a soft limestone sourced from nearby quarries, most recognized for its bright, slightly off-white shade. Like many of Italy’s centro storicos, Lecce’s located within ZTL zones to minimize traffic, meaning you’ll need a permit to enter by car. (Another option is parking right outside Porta Napoli, one of the three gates that mark the limits of the old town.) Lecce feels quite busy compared to other places in Salento, particularly in the Piazza Sant’Oronzo, which has an excavated ancient Roman theater at its center. Grabbing a near-perfect gelato at Gelateria Pasticceria Natale, Lecce’s most famous gelato shop, is sure to help you slow down, look up, and savor the city’s opulent architecture.

UNESCO World Heritage Trulli Village, Alberobello

While Puglia’s fairytale trulli houses can be found throughout the Valle d’Itria, they are at their most concentrated and best-preserved in the village of Alberobello, a UNESCO World Heritage Site. Instantly recognizable by their cone-shaped stone roofs and white facades, trulli settlements date back to the Bronze Age. The compact, rotund structures almost seem more suitable for gnomes than people, though are still used as houses today. Alberobello is exceedingly popular as a tourist destination, evidenced by kitschy souvenir shops and mediocre restaurants, though it’s still worth visiting the trulli up close. Perhaps most intriguing are the symbols painted on their stone roofs, origins unknown, but likely related to astrological and religious influences.

Don Ferrante, Dimore di Charme, Monopoli

One of the best ways to soak up Puglia’s interpretation of la dolce vita is by sipping a negroni on the rooftop of Don Ferrante, Monopoli’s premier hotel right in the center of its old town. The all-white hotel, including its rooftop décor and furnishings, contrasts brilliantly with panoramic views of the soothing blue of the Mediterranean, reminiscent of Greece’s Cycladic islands. A former fortress, Don Ferrante’s strategic location centuries ago still applies, being the most glamorous, desirable place to stay in Monopoli.

Alchemico Bar e Cose, Monopoli

Alchemico Bar e Cose translates to Alchemy Bar and Things—the “things” being a possible reference to the underground-chic interior design elements, all anchored with a floating bar that holds glowing liquor bottles three stories high. The ambiance is refreshing, if not completely uncharacteristic for the rustic Puglian charm of the surrounding town. Alchemico’s inventive concoctions are served in an unpretentious setting that’s rounded out by an atmospheric playlist that bumps through the night.

Lama Monachile Beach, Polignano a Mare

Ending a road trip at Puglia’s (perhaps even Italy’s) most photogenic—and most photographed—beach is an easy choice. Lama Monachile Beach, also known as Cala Porta, is a stunner from all angles—especially from the ancient Roman bridge that overhangs it from behind. The beach is located in a natural cove, surrounded by towering cliffs on which Polignano a Mare is built, in some places right to the very edge. Getting into the emerald water is a reward you’ll have to earn, however—trodding through the large pebbles produces a sensation that borders between massage and torture with every step. But, of course, it’s worth it.

Images by Paul Jebara