We bid farewell to Matera and begin our journey south, descending from stone into color. Our first stop is Grottaglie, a hilltop town famed for its centuries-old ceramics tradition. Within its Quartiere delle Ceramiche, artisans shape clay with practiced hands, spinning earth into delicate, sun-glazed beauty. We step inside a working studio to meet a designer from the renowned Enza Fasano family—masters of vibrant, hand-painted pottery that tells the story of Puglia in cobalt and ochre.

By late afternoon, we arrive in Lecce, the Baroque jewel of the south. Here, even the shadows feel carved. We check in at Palazzo Maresgallo, a 16th-century noble residence now thoughtfully restored as an intimate 12-room retreat. Its soaring ceilings and private gardens shelter a remarkable contemporary art collection, seamlessly woven into the palazzo’s historic fabric—each piece in quiet conversation with the past.

As the sun begins to soften, we set out on a twilight walking tour with our guide, Awdie, who grew up in Lecce. The town glows golden in the evening—its façades catching fire in the last light, its quiet lanes filled with music, marble, and mystery.  Dinner at leisure.

Lecce greets us in full sun—its palaces glowing, its piazzas alive with conversation and clinking coffee cups. Often called the “Florence of the South,” this city wears its grandeur with warmth. We begin with a private visit to the Museo Provinciale Sigismondo Castromediano, where we witness the delicate work of art restoration in progress—a rare behind-the-scenes look at how time, pigment, and devotion are patiently reconciled.

Then we step out into the living architecture of Lecce: the Basilica di Santa Croce, a masterpiece of baroque exuberance; the quiet majesty of Piazza del Duomo; and the weathered beauty of the Roman amphitheater, sunken into the city’s heart like a memory resurfaced.

Between sites, we pause to sample what the Leccese do best—caffè leccese, gelato, and the iconic pasticciotto pastry, warm from the oven and just sweet enough to require another.

The afternoon is yours: stroll, shop, or simply let the rhythm of the city guide you.

This evening, we gather in the kitchen for a private cooking demo and dinner. Watching hands in flour while sipping wine in hand, we learn the art of handmade orecchiette pasta amid laughter and stories. If beauty is Lecce’s language, tonight we speak it fluently—and with sauce.

We set out from Lecce to explore two of Salento’s treasures—Gallipoli, where the sea shapes everything, and Galatina, where art, faith, and mystery linger on the walls.

Our morning takes us west to Gallipoli, the “beautiful city” perched on a limestone island and tethered to the mainland by a single bridge. Once a powerful maritime hub, its baroque churches, sunlit piazzas, and sea-facing ramparts tell stories of trade, conquest, and devotion. We explore its atmospheric lanes, where faded palazzi lean gracefully toward the sea and laundry flutters between balconies.

Lunch is at leisure—perhaps grilled octopus at a waterfront trattoria, or a plate of sea urchin pasta tucked into a stone-vaulted wine bar. Whatever you choose, let the sea set the pace.

In the afternoon, we trade salt air for silence as we head inland to Galatina, a town of elegant restraint and hidden marvels. At its heart lies the Basilica di Santa Caterina d’Alessandria, a gothic treasure whose unassuming exterior conceals an explosion of frescoes—vivid scenes that rival Giotto, painted by unknown hands. We linger here, letting the centuries speak in pigment and prayer.

Return to Lecce in the late afternoon, with time to explore the corners of the city on your own.

Today we journey to the very tip of the Italian boot—the slender stiletto of the Salento peninsula. Our destination: Santa Maria di Leuca, where the Adriatic and Ionian Seas converge in a shimmering blue embrace. This seaside town has long been a place of crossing—for sailors, saints, and dreamers alike. Elegant 19th-century villas dot the shoreline, their Moorish and Art Nouveau flourishes hinting at a golden age of travel. We stroll the promenade, visit the hilltop Sanctuary of Santa Maria de Finibus Terrae, and take in sweeping views from the lighthouse—the second tallest in Italy.  Guests are free to explore Santa Maria di Leuca at leisure and enjoy lunch on their own. 

In the afternoon, we head north along the coast to Tricase, pausing at a hidden swimming cove where turquoise waters lap against limestone cliffs. It’s a place locals treasure—wild, elemental, and achingly beautiful.

We end the day in celebratory style at Castel di Salve, a 5th generation family-run estate producing exceptional Salento wines. Our evening begins with a private tour of the historic 19th-century cellar and vineyard, followed by a stroll through the family’s garden and courtyards in bloom—fragrant and glowing in the golden hour. As the sun begins to dip behind vineyard rows, we take our seats for a private wine tasting of Castel di Salve’s wines, perhaps a bold Primitivo and elegant rosato. The evening continues with a live performance of traditional pizzica—a fiery folk dance from nearby Taranto—before we gather for a seated dinner hosted by the family. Each course is prepared with local, seasonal ingredients and paired with their finest wines. We raise our glasses to the south—its flavors, its rhythms, and the beauty of coming all this way.

Our final day takes us east to the seaside town of Otranto, where deep blue waters meet stone ramparts and echoes of empire. Once a port between worlds, Otranto’s cobbled lanes wind through whitewashed buildings, artisanal shops, and breezy cafés. But the true wonder lies within the Cathedral of Santa Maria Annunziata—where an enormous 12th-century mosaic floor, laid by Norman hands, stretches like a myth beneath your feet. Look closely: here be dragons, saints, kings, and the entire Tree of Life, rendered in tiny tesserae and medieval imagination. Part of Italy’s UNESCO Tentative List, the cathedral’s medieval mosaic floor is a masterpiece of storytelling in stone.

We continue to Masseria Le Stanzie, a rustic farmhouse embraced by olive trees and sun. This working organic farm is beloved by visiting chefs for its simplicity, honesty, and soul. Lunch is a celebration of the land—slow-cooked, handmade, full of heart. Don’t be surprised if nonna herself pulls you into the kitchen to stir a pot or pinch a piece of dough.

The afternoon is yours to savor—return to a favorite Lecce corner, pick up a final keepsake, or simply rest in the quiet elegance of the palazzo.

Tonight, we gather one last time for a farewell dinner prepared by our private chef in the palazzo. The table is full, the glasses raised, and the journey—etched in memory. As the evening unfolds, we toast the places we’ve walked, the stories we’ve shared, and the beauty of traveling together with eyes wide open.