Panorama of the majestic medieval town in Matera in Italy

Cultural & Gastronomy Tour of Southern Italy in 14-Days

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Taormina, Cefalu, Brindisi, Ostuni...

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Suggested Duration

14 Days

This luxurious 14-day southern Italy tour has you traveling through revered regions and back-country villages to uncover tales of ancient cultures and modern delicacies. Luxuriate on the beaches in Sicily after sipping homemade wines, marvel at spectacular views from a Norman Castle, admire art and architecture in magnificent cathedrals, witness active volcanoes, and learn how to make cannoli.

Customizable Itinerary

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Trip Highlights

  • Stroll through town and learn about the history of Taormina, which will be followed by an open-air performance at a Greek Theater that was built in the 3rd Century BC
  • Explore phenomenal scenery from the remote village of Castelmola while enjoying a uniquely flavorful almond wine
  • Indulge in a thrilling hike to the summit of Mt. Etna for a Sicilian picnic that will be complete with spectacular views
  • Admire Byzantine mosaics and ancient Norman architecture as you immerse yourself in the dynamic history of Cefalu
  • Learn the art of producing traditional Madonie Provola cheese, which will be followed with a local Sommelier who pairs these cheeses with Sicilian wines
  • Island-hop through the remote Aeolian Islands to enjoy a wine tasting in Salina and to watch Stromboli’s volcano erupt against the dark night sky
  • Craft your own cannoli in Palermo before jetting off to the sun-soaked Puglia Region in a private jet
  • Wander through the whimsical town of Alberobello as you curiously admire the unique design of a trullo
  • Uncover centuries worth of history and culture as you venture through the pre-historic streets of Matera
  • Appreciate the fine art of production of homemade Limoncello as you sip the sweet and tangy delicacy in the shade of a family-owned lemon grove
  • Cruise to the luxurious island of Capri in a privately chartered boat and explore the hilltop village of Anacapri
  • Meander through the wide streets of Pompeii to learn about ancient culture and life in the shadow of Mt. Vesuvius

Detailed Description

History is a brilliant storyteller for those who are willing to listen. You can uncover Italy’s colorful past and scrumptious cuisine on this luxurious, 2-week tour through Southern Italy. Here, time stands still, recipes have remained unchanged for generations, and ancient walls have remained firmly in place for two millennia. You will begin your tour through Southern Italy after your flight arrives at Sicily’s Catania Fontanarossa Airport. In Taormina, you will attend an open-air performance at an ancient Greek theater, where you will applaud as singers bellow out melodic notes into the night sky. You will also sip almond wine and amble through medieval streets on a deluxe food and wine tour that will introduce you to many of Sicily’s most iconic dishes. The following day, you will scale the imposing slopes of Mt. Etna, where you will enjoy a picnic with spectacular views of the vast valleys below.

Afterward, you will cross the island to visit Cefalu, where you will hike to Norman ruins that sit precariously on daunting cliffs. You will then travel to the quiet village of Castelmola, where you will taste delicious cheeses that are only made in these Sicilian hills. The following day will include a luxurious boat trip to the Aeolian Islands, where you will sample honey-sweet Malvasia wine and watch nature’s incredible display of fury when the Stromboli volcano erupts at nighttime. Your last day in Sicily will culminate with a cannoli-making class and an exclusive flight to the marvelous towns that border Italy’s Adriatic Sea.

The bleach-white walls of Ostuni will be beautifully contrasted against the green olive groves and blue waters. Upon reaching the Puglia Region, you will be provided with a tour through vast olive groves, where you will witness the process of creating a smooth and buttery olive oil. You will then visit the whimsical village of Alberobello and roam through its streets that are lined with the dome-shaped trullo. In the evening, you will partake in a cooking class that will introduce you to the region’s delightful cuisine. The following day, you will discover a culture that originated in the Paleolithic era as you meander the twisting streets of ancient Matera.

Upon reaching the glorious Amalfi Coast, you will bask in the warm sunshine that glistens off of the Tyrrhenian Sea. Lemon groves will beckon to you as you indulge in a limoncello-making demonstration that will allow you to sample the region’s famed lemon-based dishes. Afterward, you will cruise to the island of Capri and dip your toes into the refreshing waters of the Blue Grotto. You will finish your adventure by touring the preserved ruins of Pompeii and learning the time-honored art of crafting traditional Neapolitan pizza. On your final day, your driver will escort you to Naples International Airport, where you will catch your return flight home.

Starting Price

$3,845 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

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