30,000+ Verified Traveler Reviews

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 $6,300

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 618 verified traveler reviews.

Italy Luxury Anniversary Tour Review: Sorrento, Tuscany, Cinque Terre, Venice, Gondola Ride, 3 Weeks
"Zicasso’s travel agency carefully and creatively designed our dream vacation to Italy and delivered an outstanding compilation of experiences."

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Italy Trip Review: Rome, Venice, Florence, the Amalfi Coast, Lake Como, 12 Nights

The Zicasso travel team did an outstanding job in organizing our trip to Italy, including stays in Rome, Venice, Florence, the Amalfi Coast, and Lake Como. The hotels, private car and boat tours, and guides were excellent. Everything went very smoothly and was first rate. Everyone was on time, polite, and knowledgeable. It was a pleasure working with the team to finalize the itinerary and the trip was all-encompassing. Definitely five stars!

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Italy Tour Review: Monterosso al Mare, 10 Nights

We loved the hotels you selected. The drivers were prompt and the guides were good. We especially loved our guide in Florence. Monterosso al Mare was beautiful.

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Italy Luxury Honeymoon Review: Amalfi Coast, Small Towns, Capri Boat Trip, Shopping, Cuisine, 1 Week
"I would send any of my friends who wanted to travel to Italy to Zicasso to plan a seamless trip. I could never have navigated this myself."

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Italy Vacation Review: Rome, Venice, Florence, Amalfi Coast, Mola di Bari, Vatican, St. Mark's, History, Art, Beaches, 2 Weeks

The Zicasso team spent about an hour with us on the phone listening to what we wanted to see and do while we were in Italy. They came back with an itinerary that was absolutely perfect.

We went to Rome, Venice, Florence, the Amalfi Coast, and my parents home town, Mola di Bari. They planned all the hotels, tours, transportation, including air, rail, and private transport, to get us to and from everywhere. The hotels they selected were all top-notch and centrally located. 

The team was available 24/7 to assist if we needed anything. They went so far to assist my daughters in sending Mother's Day chocolates and flowers to our room on Mother's Day.  Everything was planned flawlessly!

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Italy Travel Review: Perugia, Orvieto, Rome, Cooking Class, Cuisine, 1 Week
"Zicasso’s travel company did an excellent job designing our trip and provided support when we needed to make last-minute modifications."

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