Tour

Country Roads of Southern Italy & Sicily - Classic Group
from USD 5400

Insight Vacations

Tour Code: E725M27
Vacation Type: Country Roads
Brochure:
Duration: 14 Days
Countries: Italy, Holy See (Vatican City State)

Indulge in Italy’s finest food and views during this 2-week guided tour. When in Rome, you will toss a coin into the Trevi Fountain during a walking tour with a Local Expert. In Sorrento, settle into a luxurious resort and take in the views of Mount Vesuvius, which buried Pompeii in a pyroclastic cloud of ash and lava stones in 79 A.D. Dine on traditional Apulian cuisine inside a historic trulli house – iconic to the region with their conical stone roofs. Enjoy seasonal dishes such as orecchiette, a traditional pasta of Puglia, honouring age-old recipes, with a deep connection to their land. In Palermo, a historian will take you through the old city, showing you its cathedral and the Palatine Chapel in the Palace of the Normans, where glittering 12th-century mosaics will surely take your breath away.



Map Country Roads Southern Italy Sicily Guided Tour 2026

Td Tips

  • Prepaid Gratuities E725

Gold Seal Protection

  • Gold Seal Protection

Transfer Airport

  • DEP Chargeable Transfer Hotel to Palermo Airport
  • Departure Transfer Hotel to Palermo Airport
  • ARR Chargeable Transfer Rome Airport to Hotel
  • Arrival Transfer Rome Airport to Hotel

Dining Summary

  • 7 Dinner (D)
  • 13 Breakfast (B)

Choice Highlights

  • Choose between two carefully selected activities
  • Capri: Discover the luxuriant Gardens of Augustus with a Local Expert and admire views of the Faraglioni rocks.
  • Capri: Learn about local traditions as you enjoy a tasting of limoncello.

Authentic Dining

  • Rome: Savour dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavours.
  • Alberobello: Savour a freshly prepared Farm-to-Table meal featuring recipes and flavours typical of the region.
  • Taormina: Choose from our handpicked selection of local restaurants for your Dine-Around Evening, each with its own ambience and distinctive cuisine.
  • Palermo: Experience local customs as you delve into tantalising flavours and rustic dishes served with local wine.

Insight Choice

  • Capri: Discover the luxuriant Gardens of Augustus with a Local Expert and admire views of the Faraglioni rocks.
  • Capri: Learn about local traditions as you enjoy a tasting of limoncello.

Insight Experiences

Rome: Follow in the footsteps of gladiators for a deeper insight into life in ancient Rome when you enter the Colosseum.

Make Travel Matter

Grottole: Participate in the fascinating Wonder Grottole Project. This regeneration initiative works to rehabilitate the abandoned historic centre and preserve village life. Your visit directly supports United Nations Sustainable Development Goal 11: Sustainable Cities and Communities.

Top Rated 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 the ancient Greek Amphitheatre with your Local Expert. Set on a cliff, open to the sky, take your seats and enjoy the view through the crumbling arches to Mount Etna.
  • Agrigento: Admire magnificent Hellenistic remains in the Valley of the Temples, such as the massive Temple of Concordia and clifftop Temple of Juno.
  • 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.

  • Radisson Blu GHR, Rome
  • Isabella, Sorrento
  • Grand Hotel La Chiusa di Chietri, Alberobello
  • UNAHOTELS MH Matera
  • Hellenia Yachting, Giardini Naxos
  • Federico II Central Palace, Palermo
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.

Duration: 1 Day

Accommodation: Radisson Blu GHR, Rome

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.

Duration: 1 Day

Accommodation: Radisson Blu GHR, Rome

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 town’s pastel-coloured buildings perched above the shimmering sea, welcoming you to this idyllic coastal paradise.

Duration: 1 Day

Accommodation: Isabella, Sorrento

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, Capri’s famous lemon liqueur.

Duration: 1 Day

Accommodation: Isabella, Sorrento

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.

Duration: 1 Day

Accommodation: Grand Hotel La Chiusa di Chietri, Alberobello

Day 6 The Trulli Of Alberobello Relaxed Start

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 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.

Duration: 1 Day

Accommodation: Grand Hotel La Chiusa di Chietri, Alberobello

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.

Duration: 1 Day

Accommodation: Grand Hotel La Chiusa di Chietri, Alberobello

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.

Duration: 1 Day

Accommodation: UNAHOTELS MH Matera

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.

Duration: 1 Day

Accommodation: Hellenia Yachting, Giardini Naxos

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.

Duration: 1 Day

Accommodation: Hellenia Yachting, Giardini Naxos

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.

Duration: 1 Day

Accommodation: Hellenia Yachting, Giardini Naxos

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.

Duration: 1 Day

Accommodation: Federico II Central Palace, 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.

Duration: 1 Day

Accommodation: Federico II Central Palace, Palermo

Day 14 Depart Palermo

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

Duration: 1 Day

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