Benvenuti: Your Journey Begins

Today, you depart from home and begin your journey toward Southern Italy, where history is carved in stone, olive trees trace the horizon, and every meal begins with a smile.

Some travelers may choose to arrive today, a day early, to settle in and adjust before our full adventure begins. Whether you're crossing oceans today or already sipping espresso under the Puglian sun, this is the soft beginning of something unforgettable.

Tomorrow, the doors of Puglia open wide.

Welcome to Puglia—a land of golden light, generous tables, and quiet elegance. Upon arrival at Bari or Brindisi airport or train station, private transfers will bring you to Masseria Calderisi, a lovingly restored 17th-century farmhouse nestled among ancient olive trees near Fasano. This will be your luxurious home for the days ahead—a place where history and hospitality meet under a sun-drenched sky.

If you arrive early, you’re invited to unwind at the GIOIA Pool Bar—a serene garden setting surrounded by citrus and olive trees. Stretch out on a sun lounger beneath the trees, enjoy a light lunch of Italian salads or wood-fired pizza, and cool off with a spritz or homemade gelato between swims.

As the day softens into evening, we gather in the grove for a welcome reception. Sip a chilled glass of D’Araprì—a refined metodo classico from northern Puglia—and nibble on olive oil–kissed taralli, the beloved local bite that pairs perfectly with conversation and sunset. Meet your fellow travelers and let the rhythm of the journey begin to unfold.

Dinner is served at the masseria—light, seasonal, and crafted with care. Tonight, we raise our glasses to the journey ahead.

We ease into our first full day at Masseria Calderisi, waking gently with time to adjust and breathe in the sea air, the Adriatic is just a few minutes away.  Late morning, we join Chef Pietro for a hands-on pizza-making class, starting with a harvest from the garden and ending with bubbling creations from the ancient stone oven. Lunch is served al fresco in the masseria’s piazza—fresh, simple, and shared with joy.

In the afternoon, we head inland to explore Alberobello, a UNESCO World Heritage Site known for its whimsical trulli—cone-shaped houses adorned with hand-painted symbols. Discover chapels and artisan studios tucked into these fairytale forms.

As the sun lowers, continue to Locorotondo, a luminous white hill town known for its circular old quarter and sweeping views. Enjoy a brief stroll through its peaceful lanes before gathering for a group dinner—a relaxed evening of Negroamaro poured with pride, seasonal dishes, and conversation under the southern sky.

The morning begins with coastal light and sea air as we make our way to Polignano a Mare. Built on limestone cliffs carved by centuries of wind and waves, the town feels suspended between sky and sea. We stroll its labyrinth of whitewashed lanes, pausing at poetry-scrawled balconies and hidden viewpoints that drop dramatically into the turquoise Adriatic. There’s time to browse ceramics or sip a caffè in the piazza before settling into a scenic lunch on your own—perhaps crudo by the cliff’s edge or handmade orecchiette beneath a canopy of lemon trees.

In the afternoon, we continue to Monopoli, where the pace slows. Fishermen mend their nets by the harbor walls. A 16th-century castle watches over the sea. We wander the old town’s sun-bleached stone streets, slipping into chapels, artisan workshops, and quiet piazzas scented with jasmine. 

This is Puglia at its most cinematic. Two towns. One perfect day.

Back at the Masseria, as evening falls, we toast the day with aperitivi and linger over dinner—fresh catch, a crisp glass of Verdeca, and the glow of soft light over our farmhouse.

We begin our morning in Martina Franca, a city of elegant contradictions—at once ornate and understated. Within its fortified walls, a theater of Baroque unfolds. Palazzi lean gracefully into narrow alleys, their wrought iron balconies interwoven with lace-like stonework. The Basilica di San Martino presides in theatrical splendor, its sculpted façade catching the morning light. We meander through marble courtyards and limestone passages, where each corner reveals a flourish, a curve, a whisper of aristocratic past.

By midday, we descend into the quiet charm of Cisternino, a whitewashed jewel perched above olive-carpeted hills. Here, we’re welcomed at Trattoria Bère Vecchie, a local favorite known for its rustic, soul-satisfying cuisine—lunch is simple, seasonal, and served with pride. (Stanley Tucci also dined here while filming Searching for Italy in Puglia!) Afterward, we stroll through the town’s ancient heart: a maze of narrow lanes, Moorish arches, and hidden piazzette where life moves to the rhythm of footsteps and church bells.

Later, we wind through the countryside to visit a historic olive oil estate, where the real treasure flows not from cathedrals but from trees. Beneath their silvery leaves, we learn the centuries-old process of pressing olives into golden oil. A tasting follows—peppery, grassy, luminous—a perfect ending to a day grounded in the beauty of what endures.

Today we journey inland, leaving the Adriatic behind as we cross the wheat-colored heart of Puglia. Our destination is Matera, but first we pause in Altamura, a town built on limestone and bread. Within its medieval walls, traditions rise like dough—slow, deliberate, and essential. Stroll through the old center, where timeworn bakeries still fire loaves in ancient ovens. At Antico Forno di Santa Chiara, in continuous operation since 1423, we taste warm focaccia pulled from a wood-burning hearth—the flavors are as elemental as the land itself. Indulge in lunch at the bakery washed down by the owner’s homemade primitivo. 

In the afternoon, arrive in Matera, one of the world’s oldest continuously inhabited cities and a place unlike any other. Its honey-colored cliffs are carved with cave dwellings, chapels, and cisterns—the Sassi, a UNESCO World Heritage Site, appear suspended in both time and stone. Nestle into 5-star Vetera, a newly opened Relais & Châteaux property carved seamlessly into the hillside, where refined design meets Matera’s raw, elemental beauty.

As twilight paints the tufa in shades of gold and rose, we head out for an evening walk to orient ourselves in this dreamlike cityscape. Dinner at leisure.

We wake in a city carved from the bones of the earth. After breakfast, we set out on a guided urban hike, tracing Matera’s ancient staircases and winding lanes. This is no ordinary city tour—it’s a journey through rooftop labyrinths, sunlit terraces, hidden courtyards, and rainwater cisterns that once sustained entire communities. Our guide brings the Sassi to life with stories of resilience, devotion, and quiet brilliance etched into stone.

In the afternoon, we cross into the wild, sacred stillness of the Parco delle Chiese Rupestri, a dramatic landscape of cliffs and silence. Here, over 150 rock-hewn churches lie tucked into the limestone—some barely visible, others adorned with fading frescoes that once glowed by candlelight. We pause in one or two of these chapels, feeling the echo of centuries beneath our feet.

The late afternoon is yours to enjoy at leisure. Wander, sketch, sip espresso, or simply sit and take in the surreal beauty of Matera bathed in golden light.

Dinner is on your own tonight—perhaps a rooftop aperitivo with sweeping views, or a candlelit cave table shared with new friends and stories from the road.

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.

Our final morning begins with a last sumptuous breakfast in the quiet elegance of the palazzo. Sunlight pours through the windows as we linger over flaky cornetti, fresh fruit, and one last perfectly made cappuccino. Conversation drifts gently—half in plans for home, half in memories made. The table feels familiar now. The faces, too.

Hearts full, plates nearly empty, we ready ourselves for departure.

Tailored transfers will bring you to Bari or Brindisi airport (or train stations), depending on your arrangements. And though we leave the palazzo behind, the rhythm of Southern Italy—the warmth, the laughter, the slow unfolding of beauty—comes with us.

Buon viaggio. Until next time!