H-Squared Travel and Adventures
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Country Roads of Southern Italy & Sicily - Classic Group

Tour, Escorted tour
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Country Roads Of Southern Italy & Sicily - Classic 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. 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.


Dining Summary
  • 2 Dinner (D)
  • 13 Breakfast (B)
  • 5 Dinner with Wine (DW)
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: Enjoy a tasting of limoncello and learn the history behind this traditional lemon liqueur.
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.
Insight Choice
  • 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.
Insight Experiences
  • 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.
Make Travel Matter
  • 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 their community. The restaurant sources their produce locally, implements a strategy to reduce their food waste and promotes sustainable agricultural practices. Trattoria Terra Madre, advances UN Sustainable Development Goal 12: Responsible Consumption & Production.
  • 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 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.
  • 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.

About Insight Vacations
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There's more to travel than simply visiting new places – join us for experiences that spark your curiosity and take you beyond traditional sightseeing. On our premium guided tours, every day is filled with fascinating facts and intriguing stories, while superior dining nourishes the body and stylish hotels rest the soul.

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Aug 23, 2025 through
Sep 05, 2025
Aug 19, 2025 7:00 PM
13 Nights from
$4,455.00 (USD)
Per Person
Book by 2025-04-25 to receive $495.00 Last Minute Deal Discount. Airfare not included
Last Minute Deal: Must book by 2025-04-25
Aug 09, 2025 through
Aug 22, 2025
Aug 5, 2025 7:00 PM
13 Nights from
$4,478.00 (USD)
Per Person
Book by 2025-04-11 to receive $497.00 Last Minute Deal Discount. Airfare not included
Last Minute Deal: Must book by 2025-04-11
Aug 30, 2025 through
Sep 12, 2025
Aug 26, 2025 7:00 PM
13 Nights from
$4,478.00 (USD)
Per Person
Book by 2025-05-02 to receive $497.00 Last Minute Deal Discount. Airfare not included
Last Minute Deal: Must book by 2025-05-02
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Prices are per-person based on double occupancy, unless otherwise noted.