Your Italian escape begins with your arrival in Rome, where you're greeted and taken on a scenic three-hour journey south toward the Sorrentine Peninsula. Arriving in Sorrento, you'll check in and take your first steps through the charming streets of the old town, lined with citrus trees and family-run shops. Enjoy a nice dinner in the historic town before wandering the cobble-lined streets for dessert. The evening offers a welcome aperitivo with views over the gorgeous bay, setting the tone for the days ahead.

Overnight: Sorrento

Today, you’ll journey along one of Italy’s most iconic drives: the winding Amalfi Coast. Your first stop is Positano, the vertical village with its pastel-hued buildings cascading down to the sea. Stroll through bougainvillea-covered alleyways, browse local linen shops, and enjoy a seaside espresso. Continuing to Amalfi, explore the stunning 9th-century cathedral, relax at the waterfront, or savor gelato by the marina. In the afternoon, ascend to the hilltop town of Ravello, where terraced gardens like Villa Cimbrone and Villa Rufolo offer panoramic vistas of the coast. Return to Sorrento in the evening for dinner under the stars.

Overnight: Sorrento

A day of sun-soaked glamour awaits as you set off on a private boat excursion to Capri. Glide across the Tyrrhenian Sea, circling the island’s rugged coastline, and if weather allows, enter the mystical Blue Grotto. Once ashore, explore the elegant piazzas and gardens of Capri town, take the chairlift from Anacapri to the summit of Monte Solaro, or enjoy a relaxed lunch overlooking the cliffs and sea. Boutique shopping, Roman ruins, and scenic trails await. After a leisurely afternoon, cruise back to Sorrento with golden light dancing on the waves.

Overnight: Sorrento

Leaving the coast behind, you’ll journey inland to the extraordinary city of Matera in the region of Basilicata. The rolling hills gradually give way to a surreal landscape of ancient stone and honey-colored cliffs. Upon arrival, embark on a guided tour of Matera’s famed Sassi districts, a labyrinth of cave dwellings, rock-hewn churches, and stair-stepped alleys. Learn how this once-forgotten city became a UNESCO World Heritage site and a symbol of rebirth before enjoying a nice dinner in one of the many restaurants along Matera.

Overnight: Matera

This morning, head east to the sparkling Adriatic and the fortified port town of Otranto. Once a key gateway between East and West, Otranto’s dramatic seaside views, medieval castle, and stunning 12th-century cathedral—home to one of Europe’s largest mosaic floors—tell stories of conquest and culture. After a relaxed lunch on the waterfront, continue north to Ostuni, affectionately called la città bianca for its whitewashed architecture glowing against the olive-dotted hills. Spend the evening wandering the old town’s labyrinthine streets, sipping local wine on a terrace as the sun sets over the Puglia region.

Overnight: Ostuni

After breakfast, travel into the heart of the Itria Valley to Alberobello, the storybook village known for its trulli—cone-roofed stone homes unlike anything else in the world. Explore the two historic districts, Rione Monti and Aia Piccola, where you’ll learn about the trulli’s origins and craftsmanship. Visit the Trullo Sovrano and shop for local crafts in tiny, trulli-shaped boutiques. Tonight, you’ll sleep in your very own trullo, immersing yourself in the fairytale setting, with a dinner featuring handmade orecchiette and rustic local wines.

Overnight: Alberobello

The Itria Valley is dotted with some of Italy’s most enchanting villages, and today you’ll explore a few of its hidden treasures. Wander the perfectly circular old town of Locorotondo, known for its pristine alleys and flower-laden balconies, then visit Martina Franca with its Baroque palazzi and bustling markets. Alternatively, spend the day in a hands-on cooking class, mastering traditional Puglian recipes in a countryside masseria. Cap the day with a relaxed wine and olive oil tasting before returning to Alberobello for another magical night.

Overnight: Alberobello

Departing Alberobello, head to the cliffside town of Polignano a Mare, perched dramatically above the Adriatic Sea. Stroll through its poetic alleyways, stop for a signature caffè speciale, and marvel at Lama Monachile beach from above. In the afternoon, set sail on a boat tour along the rugged coastline, where you’ll discover sea caves, natural arches, and spots perfect for a refreshing swim. Optional visits include the museum of Domenico Modugno (singer of Volare) or cliffside dining in a natural grotto—an unforgettable setting to close out the day.

Overnight: Polignano a Mare

As the journey winds back toward central Italy, make your way to Tivoli, a peaceful retreat just outside Rome. Spend the afternoon discovering the magnificent Villa d’Este, a 16th-century marvel of fountains, terraces, and manicured gardens. The cascades and water features here are not just beautiful—they're masterpieces of Renaissance engineering. For those eager to explore further, Villa Adriana—Emperor Hadrian’s sprawling Roman complex—is a nearby alternative. In the evening, enjoy a farewell dinner in Tivoli’s atmospheric old town, reflecting on the journey’s unforgettable highlights.

Overnight: Tivoli

After breakfast, transfer to Rome’s Fiumicino Airport for your departing flight. Whether your heart was captured by the cliffs of Positano, the stone-carved secrets of Matera, or the quiet poetry of Puglia’s countryside, this journey leaves you with a deeper appreciation for the south of Italy—a place where history, hospitality, and beauty intertwine in every moment.

Optional: Spend an extra last night in Rome to explore the capital of Italy and discover the history, art, and culinary experiences that it has to offer before your return.