Bari Vecchia is the old heart of Puglia's capital, a knot of narrow streets where Greek, Roman and Norman history sit layer upon layer. The Basilica di San Nicola draws pilgrims from across the Mediterranean, while Bari Cathedral and the Norman-Swabian castle anchor the quarter's Romanesque and Baroque architecture. Come mid-morning, the piazzas fill with a different kind of history: local nonnas rolling orecchiette by hand on trestle tables set outside their front doors, the pasta left out to dry in the sun. That is Bari Vecchia's real appeal, not a fixed set of monuments, but streets still lived in, with cafés and boutiques tucked between centuries-old façades.

Alberobello owes its UNESCO World Heritage status to a form of building found nowhere else: trulli, conical limestone dwellings built without mortar, their roofs stacked from stone that could once be dismantled overnight to avoid taxation. Walking through the Rione Monti district, a local guide can explain how these small, whitewashed houses became a defining symbol of the Valle d'Itria. Beyond the guided history, Alberobello rewards slower exploration, with courtyards given over to local crafts and doorways opening onto workshops where the trulli's practical origins remain visible in daily use.

Lecce has earned its nickname, the Florence of the South, through a local limestone soft enough to carve into elaborate Baroque flourishes and pale enough to glow at sunset. Piazza Sant'Oronzo, built around a Roman amphitheatre, sits at the centre of a historic core that includes the Basilica di Santa Croce and Lecce Cathedral, both rich with detailed carvings. Beyond the well-known piazzas, Explora Journeys offers private guided access to Palazzo Morisco, a historic noble residence rarely open to visitors, giving guests a more considered view of the city's aristocratic past.

Brindisi has welcomed travellers for more than 2,000 years, its natural harbour long a crossing point between Italy and the eastern Mediterranean. Roman columns and Renaissance façades sit easily within a working port city, one whose real appeal lies just beyond it. For Explora Journeys guests, Brindisi opens onto the vineyards, olive groves and stone-walled countryside of southern Puglia and Salento; our Brindisi travel guide traces those routes in more detail. At a family-run winery outside the city, guests walk among vines and olive trees with a local winemaker before tasting the estate's wines alongside regional snacks.

In Puglia, food is inseparable from landscape. Orecchiette, hand-rolled and pressed with a thumb into their signature curve, still appear on trestle tables in towns like Bari, while olive oil and wine trace back to groves and vineyards that shape the countryside itself. Explora Journeys' Shore-to-Table experiences in Bari and Brindisi lead guests through these landscapes directly, walking among olive groves before sitting down to lunch prepared from produce grown nearby. In Brindisi, a Meet the Winemaker experience introduces the region's winemaking families as part of the wider Mediterranean culinary programme. For a fuller picture of the region's culinary identity, see our guide to how to eat like a Barese.

Arriving in Puglia by sea offers a different vantage than the typical road trip, with Bari and Brindisi serving as gateways to inland towns, vineyards and coastline that would otherwise take a self-driven Puglia itinerary the better part of a week to link together. Explora Journeys' winter Mediterranean Journeys collection aboard EXPLORA II carries Puglia into a season when the region's sunshine softens, setting the scene for unhurried days away from the summer crowds. It sits within a wider programme of luxury Mediterranean cruises across the region, each season offering its own perspective on the same coastline. Seen this way, the Journey itself becomes part of the discovery: the coast read from the water, before Bari or Brindisi opens onto the towns, food and countryside beyond the port.