Milan Cathedral in Italy, the third largest church in Europe.

Northern Italy to Sicily: Italy Tour for Second Timers

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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

Milan, Bologna, Perugia, Trani...

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Suggested Duration

14 Days

Open your eyes to the expansive plains of Umbria and vast olive groves of Puglia, the seaside ambiance of Calabria and the flavors of Emilia-Romagna during your personalized Italy tour that will immerse you in the marvels of discovery. Savor the authentic beauty of medieval towns and Baroque cities preserved in time and steeped in tradition. Greek theaters decorate the landscape of Sicily and caves pockmark the soft tufa limestone of Basilicata. Travel from the Adriatic’s turquoise waters to the...

Customizable Itinerary

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Trip Highlights

  • See the remarkable figures and fascinating depiction of the last meal of Jesus and the disciples when seeing da Vinci’s, The Last Supper in Milan
  • Sample the remarkable flavors of wine grown on the slopes of Mount Etna using the volcanic soils for fortified flavors
  • Embrace the magnificent colors, vibrant images, and gilded backgrounds of the Byzantine mosaics in Ravenna’s preserved churches
  • Stroll through the ancient Greek history on which Siracusa was founded including the largest and oldest Greek Theater remaining in the world
  • Learn the art of creating original Parmigiano Reggiano during a semi-private cheese-making tour before sampling a recently opened wheel
  • Witness the fascinating display of grace and devotion in the multi-tiered complex of St. Francis Basilica in Assisi
  • Navigate the layers of history in Matera, known for the Paleolithic caves used as housing for locals up until the 1960s set beneath medieval architecture
  • Wander the storybook ambiance of Alberobello emanating from the distinctive whitewashed homes with conical roofs known as trulli
  • Celebrate the depth of history around the southern edges of the Italian Peninsula when viewing the irreplaceable Riace Bronzes in Reggio Calabria
  • Delight in the flavor of Italy’s liquid gold with an olive orchard tour and olive oil vineyard offering more insight into the splendors of the tasty ingredient

Detailed Description

To experience an authentic Italian atmosphere, move away from the streets of Rome and canals of Venice during your 14-day tour of Italy that will celebrate the classical charms and scenic grandeur.  Travel from Milan to Perugia, Trani to Taormina in an all-encompassing Italian vacation perfect for first-time visitors eager to find the peninsula’s genuine heritage or repeat visitors interested in uncovering a new point of view. Take note of the distinctive differences between Northern, Central, and Southern Italy as the scenery, culture, and cuisines change. Relax on stylish beaches and let unparalleled art capture your attention in the often-overlooked corners of the country.

The remarkable differences of Italy’s regions come to light upon your arrival in Milan, located in the region of Lombardy. When visiting the six areas of Lombardy, Umbria, Emilia-Romagna, Puglia, Calabria, and Sicily, their respective histories highlight the heritage that ranges from the ruling class to the architecture, artwork to the ingredients of popular local dishes. The city of Milan not only acts as a perfect introduction to the surrounding region but also as a classic welcome to Italy as one of the most industrious cities in the country and home to classic castles and Leonardo da Vinci’s The Last Supper. The region of Emilia-Romagna contains the fascinating cities of Parma, Bologna, Ferrara, and Ravenna each with their own unique allure ranging from opera and crafting the famous Parmigiano Reggiano cheese to overlooked Renaissance majesty, enchanting culinary creations, or an intricate network of gilded Byzantine mosaics.

The region of Umbria hosts the cities of Perugia, Gubbio, Spello, and Assisi. The diverse towns retain a sense of their medieval past with a luster surpassing the more famous hilltop towns of neighboring Tuscany. The incredible allure of narrow cobbled lanes, decadent chocolates, dramatic castles, and a connection to the life and times of Saint Francis will engage your every sense. The scenic drive to Puglia allows you time to stop in one of the marvelous seaside towns of Abruzzo, such as Vieste, which is a region yet to be uncovered by foreign tourists. Puglia contains the towns of Trani, Polignano a Mare, Alberobello, and Lecce. Each town reflects a different lifestyle on the heel of Italy’s boot ranging from a thrilling cliff diving to storybook homes, Baroque extravagance to tranquil whitewashed architecture in a region producing the largest single amount of Italy’s olive oil.

Passing through the region of Basilicata has you stop in the captivating town of Matera, known for the cave-dwellings used since 7000 BC. Beyond the mixture of medieval and ancient sites takes you to Calabria, the toe of Italy’s boot-shaped peninsula. The coastal region fills with charms in the town of Pizzo and Reggio Calabria. Coastal beauty along bleached cliffs and quiet cobbled lanes or accessibility to one of the most important finds Greek archeological finds in Italian history.

Across the Messina Strait stands the stunning island of Sicily with the cities of Taormina, Acireale, Siracusa, and the infamous peak of Mount Etna. Exploring the slopes of the iconic volcano reveals enticing vineyards. The cities reflect the beauty of the sea, the charm of panoramic views, and the ways in which rebuilding communities add extra layers of majesty to historical architecture. From a cherished Carnivale to the best-preserved collection of Greek construction, Sicily personifies the treasures of greater Italy marking the perfect end to your excursion into the authentic peninsula. Looking for the best Italy travel experiences? Consider browsing our Italy travel reviews page.

Starting Price

$4,545 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.

Reviews of Zicasso's Referral Service

4.89 stars based on 5257 reviews.

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