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14 Day Italy Itineraries

Ratings of Zicasso's Service

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.

How Zicasso Works

  1. 1.

    Describe your dream 14-day Italy itinerary.

  2. 2.

    We match you with up to 3 top travel specialists (travel agencies). They compete to plan your vacation.

  3. 3.

    Book the trip when you are satisfied.

Ratings of Zicasso's Service

Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

San Gimignano in Tuscany, Italy

Custom Cultural Italy Tour in 2 Weeks

14 Day Custom Tour

From $3,845

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

Perfect Two Weeks in Italy Tour 2022-2023

14 Day Custom Tour

From $3,845

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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Wonderful honeymoon in Italy

An Unforgettable Honeymoon in Italy

14 Day Custom Tour

From $3,845

Your first trip as a married couple should be remarkable. It should be filled with fine food and fun times, dictated by nothing but the slow circuit of the sun across a cloudless blue sky. It should be notable for its uniqueness, taking you to places you’ve never heard of and showing you things you could have never imagined. It should be as bold and as boundless as your love for each other, which means it 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

From $3,495

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

From $3,845

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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Basilica of Santa Maria della Salute, Grand Canal, Venice, Italy

Italy Tour of the Most Beautiful Towns & Villages

14 Day Custom Tour

From $3,845

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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Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.

Reviews of Zicasso's Referral Service

4.89 stars based on 4167 reviews.

Northern Italy & Sicily Travel Review: Taormina, Bologna,...
"If I was to use 2 words t describe our travel designer,...

Reviewed By Ravi O.

Luxury Honeymoon Trip to Italy Travel Review: Praiano, Capri...
"The itinerary was lovely for our honeymoon."

Reviewed By Jennifer B.

Italy Trip Review: 9-Night Vacation to Rome, Sicily &...
"Laura was crucial in making the agenda and listening to...

Reviewed By Tim L.

Northern Italy Travel Review: Milan, Lake Como, Lake Maggiore,...
"The travel designer was extremely good to deal with, very...

Reviewed By Michael P.

Italy, Greece & Egypt Trip Review: 2-Week Honeymoon...
"Mary Bai was phenomenal to work with. I highly recommend...

Reviewed By Brooke G.

Sicily, Italy Travel Review: Cefalu, Palermo, Family History,...
"I highly recommend this travel agency."

Reviewed By Mary P.