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14 Day Italy Itineraries & Vacation Packages

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.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

San Gimignano in Tuscany, Italy

14 Day Trip IdeaFrom $6,300

Custom Cultural Italy Tour in 2 Weeks

Rome, Florence, Siena, San Gimignano, Chianti +2 more
St Mark's Basilica in Venice, Italy

14 Day Trip IdeaFrom $6,200

Luxury Italy Tour in 14 Days

Milan, Como, Venice, Florence, Pisa +19 more
Siena at sunset in Italy

14 Day Trip IdeaFrom $6,300

An Unforgettable Honeymoon in Italy

Venice, Florence, Montelpulciano, Val d’Orcia, Siena +4 more
Milan Cathedral in Italy, the third largest church in Europe.

14 Day Trip IdeaFrom $5,700

Northern Italy to Sicily: Italy Tour for Second Timers

Milan, Bologna, Perugia, Trani, Ostuni +16 more
View of the city of Assisi and the Sacro Convento monastery, nowadays theological seminary, Italy

14 Day Trip IdeaFrom $6,300

Amazing 14-Day Italy Itinerary with Capri

Rome, Sorrento, Vatican City, Capri, Assisi +8 more

14 Day Trip IdeaFrom $6,300

Italy Tour of the Most Beautiful Towns & Villages

Rome,  Naples, Pompeii, Amalfi (Amalfi Coast),  Spoleto and Valnerina +9 more

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  1. 1.Share Your Travel Dreams

    Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.

  2. 2.Meet Your Travel Specialists

    To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.

  3. 3.Design Your Perfect Journey

    Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

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4.9

Reviews of Zicasso's 14 Day Italy Itineraries & Vacation Packages

Based on 6061 verified traveler reviews.

Ken M.
Italy Vacation Review: Florence, Private Tour, 10 Nights

Working with Zicasso’s tour operator and the travel specialist was outstanding. The travel specialist not only listened to what we needed, but delivered. Thanks for everything.

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Linda H.
Italy Tour Review: Vatican City, Cooking Class, 9-Day Trip

We were very pleased with the reservation experience. Zicasso’s trip coordinator was helpful many times and was able to guide us through our first visit abroad.

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Olivia K.
Italy, France Trip Review: 2 Weeks

Zicasso’s tour operator created a wonderful trip for us to Italy and France! All of the transportation and tours arranged were professional, timely, and made us feel comfortable traveling in foreign countries.

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Todd L.
Italy Travel Review: Cooking Class, 1 Week

Zicasso's travel specialist was perfect. She did everything, from tracking down lost sunglasses to making sure all our rides were available and on time. Our trip was very eventful.

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James B.
Italy Tour Review: Vatican Museum, Cooking Class, 2 Weeks

Zicasso's tour company did a wonderful job meeting our requirements. The individual guides were amazing. They were all subject-matter experts, who spoke English with an accent, but were very understandable. They were all full of additional tips and recommendations, including where to eat and tourist traps to avoid when shopping for souvenirs.

The cars were always clean and the drivers were very professional. The specialized tours were amazing, especially the pasta-making/cooking class. It was above and beyond our expectations.

There was just one minor hiccup, which the tour operator rectified immediately and above our expectation.

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Robin M.
Italy Trip Review: Rome, Florence, Tuscany, Food Tour, Wine Tasting, Art, 9 Nights

It was the trip of a lifetime! Zicasso’s travel agency planned the perfect vacation for us. Our travel specialist listened to what we wanted and delivered. It was perfect!

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