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14 Day Italy Itineraries & Vacation Packages

Ratings of Zicasso's Service
<p>Explore Italy like you never thought possible. Revel in the country’s most iconic cities, monuments, and cuisines, while also getting the distinct opportunity to uncover hidden treasures from exploring quaint villages to private tastings at countryside wineries. Discover the beauty of Italy and its many enchantments with a personalized 14-day itinerary from Zicasso.</p>

Explore Italy like you never thought possible. Revel in the country’s most iconic...

Explore Italy like you never thought possible. Revel in the country’s most iconic cities, monuments, and cuisines, while also getting the distinct opportunity to uncover hidden treasures from exploring quaint villages to private tastings at countryside wineries. Discover the beauty of Italy and its many enchantments with a personalized 14-day itinerary from Zicasso.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Ratings of Zicasso's Service
San Gimignano in Tuscany, Italy
Custom Cultural Italy Tour in 2 Weeks

14 Day Custom Tour

Dynamic pricing from $5,007

Italy is like a great masterpiece waiting to dazzle the viewer. On first impression, she amazes you with her beauty. Upon a closer look, her details and history enrapture you—as you’re awestruck by the ruins of Rome, the majesty of the Vatican and the surreal waterways in Venice. Finally, you leave changed forever by the magic of this incomparable place. We invite you to indulge in the enchanting experiences that await you in this itinerary as well as our carefully selected collection of Italy tours on Zicasso.

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St Mark's Basilica in Venice, Italy
Luxury Italy Tour in 14 Days

14 Day Custom Tour

Dynamic pricing from $4,923

Classic beauty and indelible charm will radiate from ancient ruins, Renaissance artwork, and captivating coastlines during your custom-tailored 2-week tour of Italy. The iconic wonder of Italy will seduce you with panoramas of the rugged Amalfi Coast and the glamour of St. Mark’s interior shimmering with gilded mosaics. The Colosseum reflects remarkable achievement of ancient engineering and the Uffizi Gallery displays the triumphs of spirited expression. Wander along the cherished shores of Lake Como and travel into the past while strolling down the streets of Pompeii. Embrace Italy as an embodiment of culture with classic style and timeless charisma.

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Siena at sunset in Italy
An Unforgettable Honeymoon in Italy

14 Day Custom Tour

Dynamic pricing from $5,007

Your 14-day Italy honeymoon is remarkable, filled with fine food and fun times, dictated by nothing but the slow circuit of the sun across a cloudless blue sky. It is notable for its uniqueness, taking you to the wonder of Rome and the marvels of Tuscany, the beauty of Florence and the luxuries of the Amalfi Coast for an experience that can only be done in inimitable Italy.

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Milan Cathedral in Italy, the third largest church in Europe.
Northern Italy to Sicily: Italy Tour for Second Timers

14 Day Custom Tour

Dynamic pricing from $4,545

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 Tyrrhenian’s azure hues and the Ionian’s sapphire glow uncovering whitewashed homes, pastel-colored cathedrals, and an endless inviting ambiance.

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View of the city of Assisi and the Sacro Convento monastery, nowadays theological seminary, Italy
Amazing 14-Day Italy Itinerary with Capri

14 Day Custom Tour

Dynamic pricing from $5,007

Bask in the authentic charm and the simple wonder of Italy during your custom-tailored tour taking you from Rome to Capri, Lake Maggiore to Assisi. Travel across breathtaking horizons to uncover hidden sagas while gaining cultural insight into more than 3,000 years of history. Engage with the stories of the Medici family and witness the fruits of Michelangelo’s celebrated hands. Wander through lavish galleries showing the wealth of the former aristocracy and sample the treasured flavors of the remarkable wines. Engage with the extraordinary local specialties, travel the historical castles, and bask in the majestic landscapes discovered from the Amalfi Coast to Italian Alps.

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Italy Tour of the Most Beautiful Towns & Villages

14 Day Custom Tour

Dynamic pricing from $5,007

The sensations of Italy come from traditions ingrained within the soil of the countryside and rising up through the towns and villages. On this 14-day tour through the north and south of the country you will find the most beautiful scenery displayed in Italy’s natural majesty. Climb through medieval villages and find the hidden waterfalls of Umbria, revel in the Tuscan hills and visit the marvelous art of the Renaissance. From natural magnificence to humanity’s endless striving for beatific perfection, you will find, wander, and wonder through it all.

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Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Reviews of Zicasso's Referral Service

4.89 stars based on 5108 reviews.

Italy Luxury Travel Review: Sicily, Mount Etna, 15-Day Trip...
"Our tour operator hit another home run for us with this...

Reviewed By Teresa S.

Italy Luxury Travel Review: Sicily, Two Weeks
"Zicasso’s travel agent was so organized and a great communicator....

Reviewed By Chris C.

Italy Vacation Review: Tuscany, Positano, Amalfi Coast,...
"Our trip to Italy could not have been more perfect! Our...

Reviewed By Catherine W.

Italy Luxury Travel Review: Sicily, Amalfi Coast, 14-Day...
"Bravo to our travel agent for organizing an itinerary that...

Reviewed By Stein G.

Italy Vacation Review: Amalfi Coast, Sicily, Pompeii, Mount...
"Zicasso's travel company listened carefully to the types...

Reviewed By Judy J.

Italy Luxury Honeymoon Trip Review: 14-Night Travel
"Our honeymoon to Italy was perfectly planned."

Reviewed By Gerrott F.