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14 Day Italy Itineraries & Vacation Packages

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 In 3 Simple Steps

  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

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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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.
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Every Time
24/7 support and local assistance for every moment of your vacation.

We Work With the Best Italy Travel Agents for 2 Week Tours

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More About 14 Day Italy Itineraries

Italy Travel Guide
Florence, Italy
Italy Travel Guide

From Roman ruins to the Tuscan countryside, there is something for every traveler in Italy.

Our Italy Travel Guide provides helpful tips and inspiration from must-see destinations and top activities to the best time to visit. Discover traditional food and wine, inspirational culture, and amazing cities on a personalized tour.

For more information on how to make your dream journey a reality, get connected with a top travel specialist by filling out a Trip Request.

Read More    >
Best Time to Visit Italy
Summer Tuscany scenery with red poppy flowers and grain fields surrounding cute Vitaleta chapel and Pienza on the hill in Italy
Best Time to Visit Italy

The best time to visit Italy is in the spring and early summer months, from March through June. During this time, the weather is great for the beaches, sightseeing, wine tasting, food tours, and more. Fall, particularly September and October, are also lovely times, when Italy is quieter and the fall colors are on show.

Your ideal experiences also affect the best time of the year to visit Italy for your trip. Skiing in the Dolomites is exceptional in December, while enjoying the sun-washed beaches of Sicily is best in May. Rome is brilliant in April, while Florence is stunning in September.

From wine tasting to Roman-ruin exploration and coastal sightseeing, find the best time for your experience. As a family, couple, senior, or adventure traveler, we share ideas to help you ...

Read More    >
How to Plan a Trip to Italy: Frequently Asked Questions
Skyline highlighting the architecture of Rome, Italy
How to Plan a Trip to Italy: Frequently Asked Questions

As you plan your trip to Italy, consider our tips with the following answers to the most frequently asked questions.

From dreaming of the sunflower fields in Tuscany to searching the ruins of Rome for ancient treasures, you can book a trip in Italy using our ideas as inspiration. Enjoy the pleasures of La Dolce Vita or alpine panoramas, lounging on golden beaches, or embracing rolling vineyards. It is all about finding the information you need to plan the right trip for you.

Whether you are designing a first-time Italian tour as a couple or returning to the Mediterranean jewel with family, we share how to plan a stress-free trip.

Read More    >
Top 15 Things to Do in Italy
The Roman Forum in Rome, Italy
Top 15 Things to Do in Italy

From immersive tours of ancient Rome to the intricacies of artisanal crafts, Italian gastronomy to breathtaking national parks, the top 15 things to do in Italy let travelers unravel the country’s beauty and culture.

You can witness more Unesco World Heritage Sites than in any other country or sample the enticing flavors of celebrated Italian wines. Art, architecture, gastronomy, history, and heritage highlight the depth of Italy’s quintessential allure, with a range of experiences that stretch from the Dolomite Mountains in the north to the shores of Sicily’s Lido Mazzaro in the south.

Discover the top 15 things to do in Italy for a majestic and authentic experience that brings Italian culture and unique experiences to the forefront.

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7 Best Places to Visit in Italy
A farmhouse sitting in sunny fields in Tuscany.
7 Best Places to Visit in Italy

From ancient ruins in the capital city of Rome to glistening canals in Venice, you can explore the best places to visit in Italy for inspiring travel ideas.

Italy enchants with ancient cultural riches and unique style, as well as enchanting natural beauty, from the colorful seaside Amalfi Coast towns to the golden hills of Tuscany. With endless majesty stemming from the dramatic coastline, beautiful lakes, and rolling landscapes, you can immerse yourself in the storied beauty as you explore the top places to visit.

Discover essential experiences and savor the pleasures of Italian life on a trip to the best places to go in Italy.

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Reviews of Zicasso's Referral Service

4.89 stars based on 4558 reviews.

Italy Tour Review: Sicily, Ortigia, Taormina, Positano,...
"We were very happy with Zicasso and the travel company...

Reviewed By Barry N.

Italy Travel Review: Rome, Positano, Capri, Boat Tour, Cooking...
"BEST vacation we have ever taken!! The travel company did...

Reviewed By Rachel B.

Italy Luxury Group Travel Review: Sicily, Taormina, Wineries,...
"Alex did a wonderful job planning our very memorable 2...

Reviewed By Lauren R.

Travel Review: Italy Honeymoon Vacation, Rome, Sorrento,...
"The trip itself was amazing and incredibly smooth"

Reviewed By Jack C.

Italy Vacation Review: Sicily, Private Tours, 11-Day Travel...
"We had the most amazing vacation in Sicily! The travel...

Reviewed By Sonia L.

Italy Tour Review: Sicily, Countryside, Local Cuisine, 10-Day...
"Excellent trip with everything working like clockwork."

Reviewed By Alan W.