Country Roads of Southern Italy & Sicily - Classic Group
Tour Type: Country Roads
Brochure Type Europe & Britain Premium 2026 v1
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. A restaurant's founder will share why the family uses only organic ingredients that they grow themselves ? and you will indulge in those freshly picked vegetables during a Farm-to-Table dinner featuring fresh orecchiette pasta. 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.
Authentic Dining
Brochure Type Europe & Britain Premium 2026 v1
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. A restaurant's founder will share why the family uses only organic ingredients that they grow themselves ? and you will indulge in those freshly picked vegetables during a Farm-to-Table dinner featuring fresh orecchiette pasta. 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.
Authentic Dining
- Rome Savor dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavors.
- Palermo Experience local customs as you delve into tantalising flavors and rustic dishes served with local wine.
- 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 Enjoy a tasting of limoncello and learn the history behind this traditional lemon liqueur.
- 6 Dinner with Wine (DW)
- 13 Breakfast (B)
- 1 Dinner (D)
- Capri Discover the luxuriant Gardens of Augustus with a Local Expert and admire views of the Faraglioni rocks.
- Capri Enjoy a tasting of limoncello and learn the history behind this traditional lemon liqueur.
- Rome Follow in the footsteps of gladiators for a deeper insight into life in ancient Rome when you enter the Colosseum.
- Rome Enjoy exclusive access to the Basilica of Saint Praxedes during an after-hours visit. This 9th-century basilica's simple facade guards the world's best-preserved Byzantine mosaics. The history of the church springs to life as you admire the interior
- Alberobello Dine at Trattoria Terra Madre, where owner Alessandro and his nonna have built a restaurant that focuses on sustainability and creating jobs for locals. Everything is grown organically and harvested on site, and excess produce is donated to t
- Grottole Participate in the fascinating Wonder Grottole Project. This regeneration initiative works to rehabilitate the abandoned historic center and preserve village life. Your visit advances United Nations Sustainable Development Goal 11 Sustainable C
- 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.
- 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.
- Agrigento Admire magnificent Hellenistic remains in the Valley of the Temples, such as the massive Temple of Concord and clifftop Temple of Juno.
- 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.
- 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.
- Sorrento Perched upon the cliffs, lookout to see the mighty Mount Vesuvius across the Bay of Naples.
- 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.
Call 410-638-5822 for more information or to book today! Mention code 18984214
- Tour Operator
- Insight Vacations
- Offer
- Offer valid through 3/31/2025
- Duration
- 14 Days
- Escorted
- Escorted - Yes
| Day | Destination | Description |
| Day 1 | Rome | 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 joining your Travel Director for a private visit to the Basilica of Saint Praxedes, welcomed by the Rector of the basilica. End the day getting to know your fellow travelers over Roman specialties during dinner at a local restaurant. Accommodations: Radisson Blu GHR, Rome |
| Day 2 | Rome | 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. Toss a coin into the spectacular Trevi Fountain, see the Pantheon, the best-preserved monument from the Roman period, and enjoy free time to do as the Romans do. Perhaps join a tour to discover the incredibly characteristic Roman quarter of Trastevere. Get off the beaten track and explore Rome's most untouched and unique districts and most consistently unchanged medieval neighborhoods, Trastevere is dotted with ancient and dimly lit churches, crumbling buildings and streets barely wide enough for a Fiat. With your Local Expert, explore the medieval labyrinth of alleyways and pause from time to time to take in this very atmospheric area. A maze of food shops, art galleries, cafes, apartment buildings and pretty squares, this district was once rather run-down and working-class, but has now become one of the city's liveliest and most popular neighborhoods. Accommodations: Radisson Blu GHR, Rome |
| Day 3 | Sorrento | Rome: Meet your Local Expert for a guided visit to one of the icons of the Roman era. Enter the Colosseum and imagine the roar of the spectators as you hear stories of how ancient Romans liked to be entertained. Later, depart for Sorrento. Accommodations: Isabella, Sorrento |
| Day 4 | Sorrento | 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. Accommodations: Isabella, Sorrento |
| Day 5 | Alberobello | Pompeii and Alberobello: Start your day in Pompeii, buried in A.D. 79 by the historic eruption of Mount Vesuvius. Walk with your Local Expert through the cobbled streets to see a city frozen in time. Venture on to Alberobello. Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello |
| Day 6 | Alberobello | The Trulli of Alberobello Relaxed Start: Admire another of Italy's record number of UNESCO World Heritage Sites with a Local Expert. The trulli of Alberobello are circular structures with conical roofs that are domed within. They are built from local limestone and stacked without using mortar. In the evening, join a MAKE TRAVEL MATTER Experience using home-grown organic and locally sourced, seasonal produce, you sit down to a delicious four-course, Farm-to-Table dinner. Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello |
| Day 7 | Alberobello | Alberobello at Leisure Relaxed Start: The day is free for you to enjoy. Perhaps choose to visit Lecce - often referred to as ?the Florence of the south' - with its dazzling architecture and beautiful Baroque buildings. Later, relax and indulge in the amenities of your remarkable hotel. Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello |
| Day 8 | Matera | Journey South to Matera Relaxed Start: 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. Accommodations: MH Matera Hotel |
| Day 9 | Taormina | 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. Accommodations: Hellenia Yachting Hotel & SPA |
| Day 10 | Taormina | 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. Accommodations: Hellenia Yachting Hotel & SPA |
| Day 11 | Taormina | 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 Taormina at your leisure, or to embark on an Optional Experience to Syracuse. In the evening, venture to a local restaurant for a tasty meal accompanied by wine. Accommodations: Hellenia Yachting Hotel & SPA |
| Day 12 | Palermo | 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. Accommodations: NH Palermo |
| Day 13 | Palermo | 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. Accommodations: NH Palermo |
| Day 14 | Palermo | Depart Palermo: Your journey draws to an end. Departure transfers arrive at Palermo Falcone-Borsellino Airport. Accommodations: |
- Dates/Pricing
- Disclaimer
- Twin prices are per person.
- These prices are correct at the time of the website going live, however are subject to confirmation at the time of booking.
- All tour information is correct at time of tours going live, however is subject to change, please confirm all details at time of booking.
- For full terms and conditions, please refer to our Conditions page.
- Hotel Class Key: D: Deluxe SF: Superior First Class F: First Class
