People have lived here since prehistory. The Greeks traded along this coast, and the Romans ran the Via Traiana through the area on its way to Brindisi. Today's old town is small and walled. You enter through the Arco Marchesale, the only gate. Inside, the lanes are whitewashed and short, and almost every one ends at a balcony over the Adriatic.

Many of the walls have short poems painted on doors and steps. They're by a local street poet who signs himself Guido the Poet. Look for his white lettering as you walk.

In November the town is quiet and local again. The light is lower and golden, and the sea often looks clearest after a wind.

Monopoli grew rich on sea trade in the Middle Ages and kept its fortifications into the 1500s. The castle was rebuilt under Emperor Charles V, so it's known locally as the Castello Carlo V. It sits on the point where the walls meet the sea.

The town's patron is the Madonna della Madia. Legend says that in 1117 her icon arrived floating on a raft of beams (madia) at just the moment the builders of the cathedral had run out of timber for the roof. The beams went into the roof and the icon into the church. Monopoli still celebrates her arrival.

Around the town are more than 100 rural churches and masserie. Many of the farms that produce the area's oil are a few kilometres inland, where Santo Scalone is.

From the 1500s the coast was often raided by Ottoman and Barbary pirates. Landowners built their farms like small fortresses. They had a defensive tower, few windows at ground level and, in some, machicolations for dropping things on attackers. Inside were the owner's house, workers' rooms, stables, a chapel and storerooms. There was often an underground mill (frantoio ipogeo) carved into the rock to press olives at a steady temperature.

Many masserie fell empty in the 20th century, as farming changed. Over the past 30 years many have been restored as hotels and restaurants, and the best ones still farm their land. Santo Scalone is a working olive estate, which is why your tour comes with the harvest in full swing.

The landscape around you is the Piana degli Ulivi Secolari, the “plain of the centuries-old olive trees”. Some of the trees between Monopoli, Fasano and Ostuni are well over a thousand years old, with trunks twisted into extraordinary shapes.

The hill has been lived on for a very long time. In a cave nearby, archaeologists found the 28,000-year-old skeleton of a young woman who died while pregnant. Known as Delia, she's now in the town's Museo di Civiltà Preclassiche.

The whitewash is practical as much as pretty. Lime was cheap and local, and it reflected the summer heat and lit the dark alleys. It was also used as a disinfectant, notably during plague outbreaks in the 1600s. People still renew it every year.

At the top stands the cathedral, built in the late 1400s. Its facade combines a Gothic shape with one of the most beautiful rose windows in southern Italy. Just below is Piazza della Libertà, the town's living room, with its tall baroque column to Sant'Oronzo, the patron saint who is credited with saving the town from plague.

From the 1500s the coast was often raided by Ottoman and Barbary pirates. Landowners built their farms like small fortresses. They had a defensive tower, few windows at ground level and, in some, machicolations for dropping things on attackers. Inside were the owner's house, workers' rooms, stables, a chapel and storerooms. There was often an underground mill (frantoio ipogeo) carved into the rock to press olives at a steady temperature.

Many masserie fell empty in the 20th century, as farming changed. Over the past 30 years many have been restored as hotels and restaurants, and the best ones still farm their land. Santo Scalone is a working olive estate, which is why your tour comes with the harvest in full swing.

The landscape around you is the Piana degli Ulivi Secolari, the “plain of the centuries-old olive trees”. Some of the trees between Monopoli, Fasano and Ostuni are well over a thousand years old, with trunks twisted into extraordinary shapes.

Trulli are an ancient building technique of the Murgia. They're made from limestone dug from the fields and stacked dry in a false dome, with a thick wall below. The roof is finished with a decorative pinnacle (pinnacolo), which is said to have identified the builder or brought good luck.

The story everyone tells is about tax. In the 1600s the Counts of Conversano are said to have ordered peasants to build without mortar. The houses could then be dismantled quickly when royal inspectors came, so they wouldn't count as permanent buildings. Whether or not it's true, Alberobello received royal recognition as a town in 1797, and today the trulli are a UNESCO site.

There are two trulli districts. Rione Monti is the larger and busier, with over 1,000 trulli climbing the hill, many of them now shops. Aia Piccola is quieter and residential, with about 400 trulli, and it's where you'll see more ordinary life.

From the valley floor you can see why it's called the round place. The medieval centre forms a near-perfect circle on top of the hill. Inside, the streets are spotless, whitewashed and full of flowers, with wrought-iron balconies and carved doorways.

Look up at the roofs. The town's typical houses are the cummerse, with steep pitched roofs made of stone slabs called chiancarelle. They're a cousin of the trulli, but a gabled rather than conical form, and found almost only here.

The surrounding countryside is wine country. The local white, Locorotondo DOC, is made mostly from Verdeca and Bianco d'Alessano grapes. It's fresh and light, and very good with the region's seafood.

Bari's great moment came in 1087. A group of Bari sailors took the relics of Saint Nicholas from Myra, in what is now Turkey, and brought them home. The Basilica di San Nicola was built to house them, and it became one of the major pilgrimage sites of the Middle Ages. It's still important to both Catholics and the Orthodox world. Saint Nicholas is, of course, the saint behind Santa Claus.

For decades Bari Vecchia had a rough reputation. Since the 1990s it has been restored and is now one of the most enjoyable old towns in the south. It's safe, alive and very local.

Strada Arco Basso and the lanes around it are famous for the women who make orecchiette by hand at tables outside their homes, then dry them on wooden screens. You can watch, and often buy a bag to take home.