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Country Roads of Southern Italy & Sicily (Small Group)

14 Days Rome to Palermo
Country Roads of Southern Italy & Sicily (Small Group)
Country Roads of Southern Italy & Sicily (Small Group)
Country Roads of Southern Italy & Sicily (Small Group)

Overview

Book online and enjoy exclusive savings on Insight Vacations 14 Day Country Roads of Southern Italy & Sicily (Small Group). 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 read more 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.
Sold Out
There are currently no departures available on this trip. Either the season has ended and new dates will be released soon, or the itinerary has been updated and isn’t operating this season.
Trip Length
Trip Length

14 Days

Trip Starts
Trip Starts

Rome

Trip Ends
Trip Ends

Palermo

Countries Visited
Countries Visited:
Trip Style
Trip Style

Country Roads

Accommodation
Accommodation

4 - 4.5 Star

Budget
Budget

Premium

Age Range
Age Range

5-99 Years

Max. Group Size
Max. Group Size

24

Guide Style
Guide Style

Fully Guided

Tour Code
Tour Code

SE725

Itinerary

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. (D) Stay: Radisson Blu GHR, Rome

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. (B)

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. (B) Stay: Isabella, Sorrento

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. (B/D)

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. (B/D) Stay: Grand Hotel La Chiusa di Chietri, 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 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. (B/D)

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. (B)

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. (B/D) Stay: UNAHOTELS MH Matera

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. (B/D) Stay: Hellenia Yachting, Giardini Naxos

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. (B)

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. (B)

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. (B) Stay: Federico II Central Palace, 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. (B/D)

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

Trip Inclusions

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

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.

  • 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.

  • 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.
  • Dining Summary: 7 Dinners (D), 13 Breakfasts (B)

  • Itinerary and inclusions are subject to change
  • Price is for land, cruise and internal flights as specified. Flights not specified are not included

Operator

Insight Vacations
At Insight Vacations we have been creating magical travel experiences for over 40 years, showcasing the most outstanding destinations and curated experiences in Europe and North America.

Why are we different to any other operator? It’s our unique Insight experiences. It’s our authentic and varied dining options, it’s t moreravelling in smaller groups on customised coaches with twice the legroom, it’s staying in the right hotels in the right location, all brought together seamlessly by our exceptional travel directors. In essence: All the sights, and the insights….up close and personal…in comfort and style.

Travel is such a joy and a personal passion for myself and every member of our team. We’re so proud of the quality, service and value we provide and invite you to try it for yourself. Talk to Global Journeys to find out more about travelling in style and booking your next holiday with Insight Vacations.
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Insight Vacations Europe, Britain & the World (2026-27)

Discover premium guided journeys across Europe, Britain, North Africa, the Americas and Asia, where iconic cities, breathtaking landscapes and rich cultures come to life. Enjoy carefully crafted experiences, small group sizes and superior comfort, including luxury coaches and seamless end to end service. From world wonders to hidden gems, every detail more is designed to deliver an elevated and unforgettable holiday.

Prices & Dates

There are currently no departures available on this trip. Either it's the end of the season and new departures will be released shortly, or this itinerary has been changed and is not operating this season. Feel free to contact us for information about when next seasons dates will be released or click here to view general release dates for all destinations.

Note
Tour & cruises prices are per person. Prices shown have savings applied, are subject to availability and may be withdrawn at any time without notice. Pricing and trip details are correct at this point in time, however are subject to confirmation at the time of booking and are subject to change by Insight Vacations. For cruise itineraries, cabin images are sourced from the cruise-line and should be treated as indicative only. Cabin inclusions, upholsteries and room layout may differ to the image(s) shown depending on the ship selected and your sailing dates.

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