Country Roads of Southern Italy & Sicily - Classic Group - 11 Apr 2026 to 10 Oct 2026

Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Settle in, before meeting your Travel Director. Later today, get to know your fellow travellers over Roman-specialities dinner at a local restaurant.

Rome is about art, antiquity, piazzas and palaces, and our guided walk with a Local Expert has it in abundance. Sightsee the local way, with a leisurely passeggiata through the backstreets, where a friend in Rome will explain how modern life takes place. Cross the Tiber river to enjoy ancient Rome. Enter the Colosseum and imagine the roar of the spectators as you hear stories of how ancient Romans liked to be entertained.

As you leave the bustling streets of Rome behind, you enter the peaceful charm of the Italian countryside. The roads wind through sun-dappled hills, where fields of golden wheat and rows of olive trees stretch endlessly under a brilliant blue sky. Small villages dot the landscape, their stone houses nestled against rolling hills, offering a glimpse into authentic Italian life and the air carries the scent of wildflowers and citrus groves. The journey southward reveals itself like a beautiful postcard, with views of the sparkling Mediterranean beginning to emerge in the distance. As you approach Sorrento, the dramatic cliffs and coastal views unfold, the town’s pastel-coloured buildings perched above the shimmering sea, welcoming you to this idyllic coastal paradise.

The impossibly blue sea welcomes you to the sun-drenched island of Capri as you cruise by jetfoil. On arrival, meet your Local Expert for an orientation walk through the narrow alleyways. Explore Capri with Insight Choice. Choose to visit the immaculate Gardens of Augustus with a Local Expert and admire the views over the Faraglioni Rocks. Alternatively, enjoy a tasting of limoncello, Capri’s famous lemon liqueur.

Start your day in Pompeii, buried in AD 79 by the historic eruption of Mount Vesuvius. Walk with your Local Expert through the cobbled streets to see a city frozen in time. Then venture on to Alberobello.

Join a Local Expert to explore one of Italy’s many UNESCO World Heritage Sites — the unique trulli of Alberobello, circular limestone dwellings with domed interiors and distinctive conical roofs, ingeniously built without mortar. You may also opt to join our Local Expert for an exploration of Ostuni, a whitewashed town that echs the charm of a North African Arab Medina. Stroll through its winding cobbled streets and admire its striking architecture. In the evening, enjoy a Farm-to-Table dinner, showcasing traditional Apulian dishes made with seasonal produce.

Today is yours to enjoy at leisure or unwind and make the most of the exceptional amenities at your remarkable hotel. You can also choose to discover cliffside Polignano a Mare with a Local Expert, enjoying Adriatic views and a stroll through the historic hometown of Volare singer Domenico Modugno.

Visit Matera with a Local Expert for an in-depth exploration of the UNESCO World Heritage Site of Sassi - a labyrinth of cave dwellings, churches, staircases and arches, hewn out of the solid rock. You may recognise Matera as the biblical backdrop for the film ‘The Passion of the Christ.’ Continue to the small village of Grottole. Once a thriving community, it has lost most of its activity and population. Meet Andrea, a local striving to bring back the area's traditional way of living. On this MAKE TRAVEL MATTER® Experience explore the historic old town to learn about the fascinating history of the village and enjoy an aperitif with local snacks helping to preserve the culture.

In the morning, travel along the Violet Coast to the very t of Italy and board your ferry bound for Sicily, across the Strait of Messina. According to Grecian legend, this was home to the mythical sea monsters Scylla, a six-headed rock monster, and Charybdis, a whirlpool, based on either side of the strait. Together, they posed an inescapable threat to passing seafarers as avoiding one meant passing too close to the other. You will soon arrive at your hotel where you will spend three glorious nights on the Taormina Riviera. Join a Local Expert for a visit to the Greek Theater of Taormina, graced with the most spectacular of backdrops. Stroll along the elegant Corso Umberto to the Piazza IX Aprile and admire the panoramic views and hews of blue from the sky to the azure sea. Later, take your pick of specially selected restaurants for your Dine-Around evening.

The day is at leisure to relax at your resort's private beach, or perhaps explore the medieval quarter? Don't miss the chance of an optional drive through the national park to Mount Etna, Europe's largest volcano.

Early risers may experience what D.H. Lawrence christened the ‘dawn coast of Europe'. The day is free to explore at your leisure, or to embark on an Optional Experience to Syracuse.

Drive to Agrigento and explore the Valley of the Temples with a Local Expert. See the massive Temple of Concord and clifftop Temple of Juno, overlooking the sea. In the afternoon, continue to the Sicilian capital of Palermo.

Join a historian on a guided walk to see the gems of the old city. Visit the amazing Palatine Chapel in the Palace of the Normans. Outside, there are few clues to its astonishing interior, completely covered in glittering 12th-century mosaics. Continue to the Palermo Cathedral which has been altered over the years and observe its unique blend of architectural styles. In the afternoon, there is free time to explore or shop in Palermo or continue sightseeing. In the evening, join your fellow guests and Travel Director at a local restaurant for a dinner of delicious local cuisine and wine.

Your journey draws to an end. Departure transfers arrive at Palermo Falcone–Borsellino Airport.