Highlights
Rome: Sightsee the local way, with a leisurely passeggiata through the backstreets, where a friend in Rome will explain how modern life takes place, around ancient treasures like the Trevi Fountain, the Pantheon and Piazza Navona.
Sorrento: Perched upon the cliffs, lookout to see the mighty Mount Vesuvius across the Bay of Naples.
Capri: Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters.
Pompeii: Walk with a Local Expert through the cobbled streets of this ill-fated town, frozen in time since the first century.
Alberobello: Led by a Local Expert, explore this UNESCO World Heritage Site showcasing the Trulli of Alberobello. Circular structures with conical roofs that are domed within, built from local limestone and stacked without using mortar.
Matera: With your Local Expert, visit the famous Sassi or cave dwellings, which were home to approximately 20,000 people until 1950s and are now a UNESCO World Heritage Site.
Taormina: Visit Taormina’s ancient amphitheatre with your Local Expert. Carved from honey-coloured stone and set high on the cliff, the theatre frames wide views of the Ionian Sea and the distant rise of Mount Etna through its weathered arches.
Agrigento: Explore the Valley of the Temples and its impressive Hellenistic ruins like the well-preserved Temple of Concordia and the clifftop Temple of Juno overlooking the Sicilian landscape.
Palermo: Discover the Sicilian capital with your Local Expert. See Pretoria Square and the 16th-century fountain. View the composite architectural styles of the Palermo Cathedral and visit the Palatine Chapel.
Matera: With your Local Expert, visit the famous Sassi or cave dwellings, which were home to approximately 20,000 people until 1950s and are now a UNESCO World Heritage Site.
Taormina: Visit Taormina’s ancient amphitheatre with your Local Expert. Carved from honey-coloured stone and set high on the cliff, the theatre frames wide views of the Ionian Sea and the distant rise of Mount Etna through its weathered arches.
Agrigento: Explore the Valley of the Temples and its impressive Hellenistic ruins like the well-preserved Temple of Concordia and the clifftop Temple of Juno overlooking the Sicilian landscape.
Palermo: Discover the Sicilian capital with your Local Expert. See Pretoria Square and the 16th-century fountain. View the composite architectural styles of the Palermo Cathedral and visit the Palatine Chapel.
Itinerary
Southern Italy and Sicily entice with a tapestry of flavors and historic marvels on the 'Country Roads of Southern Italy and Sicily' trip—a 14-day guided adventure that welcomes families and mature travelers alike. Setting out from Rome, you’ll be swept along a route that reveals the heart and soul of Italy, from the ancient streets of Catania and the sparkling shores of Taormina to Palermo’s vibrant culture and Sorrento’s dramatic views over the Bay of Naples.
Stroll Rome’s iconic sites with a local expert, tossing a coin into the Trevi Fountain as tradition dictates. In Sorrento, unwind at a luxurious resort with panoramic vistas of Mount Vesuvius, whose eruption famously preserved Pompeii. Meander through the sun-kissed hills of Apulia and savor a memorable dinner inside a historic trulli house—these unique, conical-roofed dwellings are a highlight of the region. Relish traditional orecchiette pasta and sample seasonal fare that honors Puglia’s rich agricultural heritage.
Palermo offers a deep dive into Sicily’s layered past. Guided by a historian, you’ll wander the old city, marvel at the ornate cathedral, and be dazzled by the Byzantine mosaics of the Palatine Chapel. Between immersive sightseeing and moments of leisure, the tour is perfectly paced for those who appreciate comfort and culture in equal measure.
With accommodation, transport, and meals included, this tour package affords travelers a seamless, enriching experience. The unique selling point? A rare chance to dine inside a genuine trulli house and savor authentic regional cuisine—a memory that lingers long after the final gelato. Experience Italy’s diverse landscapes and traditions on a journey crafted for lasting family memories and sophisticated exploration.
day 1 - Welcome to the Eternal City of Rome
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.
day 2 - Rome with the Locals
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.
day 3 - Rome to Sorrento
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 towns pastel-coloured buildings perched above the shimmering sea, welcoming you to this idyllic coastal paradise.
day 4 - Capri, the Isle of Dreams
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, Capris famous lemon liqueur.
day 5 - Pompeii and Alberobello
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.
day 6 - The Trulli of Alberobello Relaxed Start
Join a Local Expert to explore one of Italys 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 echoes 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.
day 7 - Alberobello at Leisure Relaxed Start
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.
day 8 - Journey West to Matera
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.
day 9 - To Sicily and the Taormina Riviera
In the morning, travel along the Violet Coast to the very toe 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.
day 10 - Free Time on the Taormina Riviera Relaxed Start
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.
day 11 - A New Dawn in Sicily Relaxed Start
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.
day 12 - Agrigento, the Valley of the Temples and on to Palermo
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.
day 13 - Palermo and the Golden Age of the Normans
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.
day 14 - Depart Palermo
Your journey draws to an end. Departure transfers arrive at Palermo FalconeBorsellino Airport.

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