For travelers who see the world as one big checklist (the Acropolis, check; the Mona List, check), Puglia probably won’t make the cut: There are no obligatory museum stops, and the longest line you’ll wait in is for a gelato, not an old-master painting. But it is precisely this off-the-map quality (tour buses are as rare as bad weather) that makes Puglia feel as if you’d wandered onto the set of Cinema Paradiso. Families come for the glorious food (locally grown figs, olives, almonds, and gapes, and just-caught seafood), the hill towns, and tiny fishing villages that feel caught in time, and, of course, the climate, which while heavenly in summer is mild year-round. Best of all, the locals adore children, so prepare to be fawned over wherever you go.
Day 1: Bari to Savelletri
Fly into Bari in central Puglia and drive down the coast to Polignano a Mare, an insanely beautiful fortified town built directly into limestone cliffs. The narrow streets and whitewashed alleys invoke Marrakesh (a reminder of Byzantine rule here during the fourth and fifth centuries). Explore the centro storico (historical center), then order a pizza and enjoy the views of the Adriatic Sea at La Balconata.
From here, it’s 20 kilometers southeast to the fishing village of Savelletri. You’ll see grove after grove of olive trees, that are so old you half expect to see a Roman soldier asleep underneath one. Check into the Masseria Torre Coccaro, which was originally a walled farm (masseria means “fortified farmhouse”), has an English-speaking staff and a traditional lido (an Italian beach club) with umbrellas, towel service, and a restaurant (that serves probably the best frutti di mare ever).
One night while you’re here, book a dinner at the Masseria Il Frantoio. It’s very sweet and informal—when you arrive the owner greets you with “Welcome home”. Peacocks roam the grounds at this agricultural estate, which serves a nine-course organic dinner. Kids are welcome, but the meal ends at 11:30, so you may want to hire a sitter at Torre Coccaro. Pick up some homemade olive oil before you leave.
Day 2: Alberobello to Ostuni
Start the day at Alberobello, a UNESCO-protected town 20 kilometers west of Torre Coccaro. This is the most touristy spot in Puglia, but for good reason: Home to the world’s largest concentration of trulli—conical-roofed houses with mysterious origins—the town looks like it’s straight out of a fairy tale. Some historians believe these pointy-topped adobe-and-stone structures (there are 1,500 in all) date back as far as two or three millennia.
Drive 12 kilometers south through the Valle d’Itria to Martina Franca, keeping an eye out for more trulli along the way. A quiet baroque town with virtually no tourism, Martina Franca is easy to navigate. No cars are permitted in its center, so park on the perimeter and walk past the San Domenico church. Be sure to point out to the kids the angels holding the crown on the church’s facade. Stop at the deco Caffè Tripoli on Via Garibaldi for a bocconotto (pastry with a cream center) and a caffè a la mandorla (coffee with sweet almond-milk syrup), or just a dreamy gelato. Then sit outside and take in the scenery.
For lunch, continue south to Al Fornello di Ricci, a Michelin Guide–starred restaurant just outside the town of Ceglie Messapico. Long meals are the way to spend afternoons in Italy, since stores close and everyone goes home from 1 to 4 p.m. Order the antipasti, the gnocchi, and the papas fritas (homemade potato chips). The restaurant will make anything for children, and later they can explore the bougainvillea bushes and the lush herb garden as you linger over coffee and dessert.
Afterward, head north to Ostuni, known as the White City for its rows of white houses. A hill town that sits high over the Adriatic Sea, it’s best navigated by foot, so park as soon as you see a spot and walk in. Head straight to Piazza Libertá, a square filled with cafés, gelaterie, and locals enjoying espresso. Earn your gelato as you walk up the steep, narrow streets: Start on Via Cattedrale, which is lined with shops that sell leather sandals, fischietti (clay whistles), colorful tops, and ceramics. Visit the cathedral at the top of the street, then walk to the Belvedere Vista Point, which overlooks olive groves that border the bright sea.
Before heading back to Torre Coccaro for the night, stop for a fresh seafood dinner at La Marea in Savelletri. Then stroll through the harbor and scope out all the fishing boats.
Day 3: Lecce to Marittima di Diso
From Torre Coccaro, drive south out of central Puglia and into the Salento region, known for its wines, the tarantella dance (which supposedly shook out spider bites), and pizzica (tambourine music). Follow signs to Lecce, 75 kilometers away. Referred to as the Florence of the South for its 17th- and 18th century baroque architecture, this town is filled with enchanting streets and churches. Grab a quick lunch at La Rusticana (Via V. Emanuele 31). Try the rustico—a pastry filled with tomato sauce, béchamel, and mozzarella. Just don’t call it a calzone.
Maglie, 25 kilometers south, is an elegant town with very little tourism. Make time for a coffee and a pastry at any of the cafés in the centro—also the best place to find a restroom—and pick up some of the beautifully packaged petit fruits (jelly candies with bits of almond), dark chocolate, and latte di mandorla (almond-milk syrup) at Maglio (Via Pietro Refulo 6), a chocolate shop that dates back to 1875.
Head east 15 kilometers to Otranto, a fishing village with a marina and an old town center. Stop at the cathedral, Santa Cesarea di Terme, and look at the 12th-century tree-of-life floor mosaic. Then drive south along the coast, taking in the views of the Ionian Sea as you pass the easternmost point of Italy. Visit the Grotta Zinzulusa, a deep cavern filled with stalagmites and stalactites.
Stay at Il Convento di Santa Maria di Constantinopoli, a 14th-century convent 20 kilometers away in Marittima di Diso that is now run as a hotel by an English couple. Breakfast, lunch, and laundry are included, and dinner is served nightly for about $40 a head, including beverages (the hotel will happily serve children early).
Day 4: Castro Marina to San Gregorio
Wake up at Il Convento to a decadent breakfast of peaches, figs, and fresh bread, then explore the property. While the owners’ rich collection of African, Aboriginal, and Mexican art, on display throughout the convent, is of museum quality, it’s not so much intimidating as it is fantastical. Children will love the oversize wooden (read: unbreakable) animal sculptures in particular; failing that, there’s always Pompea, the couple’s sweet sheepdog. Take a plunge in the pool, which is surrounded by palms and the high convent walls.
Before leaving, pick some wild figs from the estate, then go three kilometers south to Castro Marina. This fishing village feels wonderfully caught in the past: Visit the fishmonger’s, where the catch is so fresh that the fish are moving on the ice, and watch the boats come in from the harbor. On the other side of the marina, you can see locals taking their morning swim.
Drive six kilometers south and take a dip in the cove of Aquaviva, a local beach in Marina Marittima that has plenty of parking, a pizzeria and a snack shop, and some welcome shade. Stone terraces, filled with picnicking Italian families, surround the cove.
Keep driving south until you reach the very sole of the boot: The coast is dotted with secluded coves, and you’ll wish you could visit every one. Just past Santa Maria de Leuca, at the tip of the peninsula, is the town of San Gregorio, which has a fantastic and inexpensive fish restaurant, Da Mimi. Relax on the shady terrace and look out at the sea as your kids run around without offending anyone, because in Italy, children are royalty. As you enjoy the scene, you might wonder how you can bring some of Puglia’s way of life back home with you.
Photos: Matthew Hranek