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.