Northern Italy to Sicily: Italy Tour for Second Timers

The small Italian Town of Umbria sitting on green rolling hills
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Total Trip:

14 Days

Countries Visited:


Places Visited:

Milan, Bologna, Perugia, Trani, Ostuni, Pizzo, Taormina, Acireale, Siracusa, Polignano a Mare, Alberobello, Spello, Assisi, Gubbio, Ravenna, Ferrara, Parma, Vieste,



Departure Dates:

Dates are flexible and customizable for private departures.
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


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Customizable Itinerary

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Day 1

Milan – Arrive in Marvelous Milan with an Introductory City Tour

The fast-paced city of Milan brims with creativity thanks to a dramatic history and inspiring artwork that has turned culture into a legacy and design into a treasure. Upon arrival, your private driver will greet you at Malpensa Airport before transferring into the heart of the city. The remainder of the day is yours to explore and experience the grandeur of Milan at your preferred pace. The Galleria Vittorio Emanuele II is a luxury arcade erected in the late-19th century. The soaring central dome floats above the mosaic floors at 157 feet. The classic industrial iron and glass construction highlights the eclectic beauty of the design while framing luxury stores like Prada.

The Galleria Vittorio Emanuele II hosts the first Prada shop ever opened, which dates back to 1913, while 2019 represents the 100th anniversary of the luxury brand acting as the official supplier of the Italian Royal Family. In a tradition dating back to 1919, Prada uses the royal rope from the prestigious coat of arms in their logo reflecting distinguished sophistication and recognized splendor fit for a king. The original store retains its sense of history blending in with the modern world with an elegant display on the original shelves handmade using mahogany and adorned with quality handbags, trunks, leather accessories, footwear, and clothes from the latest collection.

What's Included:








Day 2

Milan – Discover the Splendors of Milan History and Culture

Day 3

Bologna – Enjoy the Flavors and Sites of Parma en route to Bologna

Day 4

Bologna – Explore Renaissance Ferrara and Byzantine Ravenna

Day 5

Perugia – Travel to Perugia Stopping First in Gorgeous Gubbio

Day 6

Perugia – Visit Alluring Assisi and Sensational Spello at your Leisure

Day 7

Trani – Relish a Scenic Coastal Drive to Vieste before Reaching Trani

Day 8

Ostuni – Traverse the Splendors of Polignano a Mare and Alberobello

Day 9

Ostuni – The Distinct Streets of Lecce and Enjoy an Olive Oil Tasting

Day 10

Pizzo – Navigate the Caves of Matera and Relax in Coastal Pizzo

Day 11

Taormina – Ancient History in Reggio Calabria en route to Sicily

Day 12

Taormina – The Summit of Mount Etna on a Full Day Excursion

Day 13

Taormina – Indulge in Tranquil Acireale and Sensational Siracusa

Day 14

Taormina – Transfer to Catania for your Flight Home
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