Country Roads of Southern Italy and Sicily (Summer, Classic)


Overview
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.
- Agrigento: Admire magnificent Hellenistic remains in the Valley of the Temples, such as the massive Temple of Concord 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.
- 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’s treasured collection, including Bernini's first sculpture and the renowned mosaics, illuminated for your visit. This once-in-a-lifetime experience is a rare and unforgettable insight into Rome and its religious history.
- Rome: Follow in the footsteps of gladiators for a deeper insight into life in ancient Rome when you enter the Colosseum.
What's this trip about?
Itinerary

2025 marks a Jubilee Year, a momentous Roman Catholic event celebrated every 25 years, turning Rome into a center of celebration between December 24, 2024, and December 31, 2025. As festivities unfold, itineraries may be adjusted to ensure you make the most of your ti...
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. Admire the sp...
Start your last day in Rome by joining a tour to explore the incredibly charming and characteristic Roman quarter of Trastevere. It is dotted with ancient and dimly lit churches, crumbling buildings and streets barely wide enough for a Fiat. With your Local Expert, ex...
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 Aug...
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.
Grand Hotel La Chiusa di Chietri, Alberobello
Breakfast, Dinner
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...
Today is yours to enjoy at leisure. You may wish 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. Later, unw...
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 Pa...
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 whir...
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.
Hellenia Yachting Hotel & SPA
Breakfast
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.
Hellenia Yachting Hotel & SPA
Breakfast
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.
NH Palermo
Breakfast
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 ...
Your journey draws to an end. Departure transfers arrive at Palermo Falcone–Borsellino Airport.
Breakfast
Want a tailor-made trip instead?
Your trip, your way, planned by an expert:
- You choose budget, destinations, activities, transport & lodging type
- Expert designs the itinerary for you, and once approved, takes care of logistics
Dates & Availability
Check current availability, prices, specials & more.
The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.
Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

Insight Vacations Reviews & Ratings
Other Insight Vacations Reviews
Michelle Smolan
Mar 2025
Scenic Iceland and the Northern Lights
Robbie our tour director was amazing. Knowledgeable organized friendly and efficient. Northern lights were amazing. Sky lagoon was spectacular. Spent hours there. ...
Trusted Customer
Mar 2025
Arctic exploration march 2025
Excellent tour director Lana!
Tour Operator
About Travelstride
Find your perfect trip
Save time
Save money
Travel confidently
Logistics
Accommodation
- Radisson Blu GHR, Rome
- Isabella, Sorrento
- Grand Hotel La Chiusa di Chietri, Alberobello
- MH Matera Hotel
- Hellenia Yachting Hotel & SPA
- NH Palermo
- 7 Dinner (D)
- 13 Breakfast (B)
Become a member
- Save up to $700 per person
- Access members-only specials
- Personalize trip recommendations