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.

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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 6255 verified traveler reviews.

Italy Vacation Review: 12 Days

It was a fantastic trip. Everything we planned with Zicasso’s travel company was on time and with high-quality local guides and drivers. They were very responsive and helped us build an itinerary for our 12-day trip to southern Italy. They stayed in touch throughout the planning process, helping us find restaurants and answer questions. I would highly recommend this travel company to anyone planning a trip to Italy.

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Italy Vacation Review: Sorrento, Amalfi Coast, Florence, Tuscany, 10-Night Trip

Zicasso’s travel specialist was a pleasure to work with. She helped me plan our trip of a lifetime to Italy. I told her which cities we wanted to visit and our interests, and she gave me great recommendations for tours and experiences. She was flexible with the itinerary changes I made beforehand and, after our arrival, the pre-arranged transportation was seamless and the hotels were great.

Our ambassador during the trip was very responsive when I had questions. I appreciated the daily messaging app reminders for the times and activities for the next day, including a location link on Google Maps for the meeting points. Our pre-arranged drivers and tour guides were excellent.

This holiday was everything I hoped for. If I am fortunate enough to plan another holiday to Italy, I will definitely use the travel company again! Based on this experience, I will definitely use Zicasso again for an international holiday.

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Italy Trip Review: Florence, Tuscany, Rome, Food Tour, Wine Tasting, 1 Week

We had a great trip to Florence, Tuscany, and Rome. One of the best parts about the trip was our travel company. Zicasso's travel specialist took care of booking everything we needed and doing so within budget. I didn't have to worry about keeping up with tour tickets and schedules because he had already taken care of all that. He was also available for quick questions and updates while we were on our trip. We couldn't have asked for better!

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Italy Trip Review: Rome, Florence, Vatican, Sistine Chapel, Colosseum, 2 Weeks

Zicasso set us up with a wonderful travel agent. The process of choosing and communicating through the Zicasso system was easy and helpful.

The travel specialist and her team planned a wonderful 15-day trip, with nine days in Rome and four days in Florence. She found us great accommodations that included a kitchen, which was a must for us. Other travel agents were not able to provide such accommodations.

The drivers we had were professional and picked us up on time. The guides were experts in their field and generally had taught at universities. The guides were very personable and tailored the tours to our interests.

She arranged all the necessary skip-the-line tours. We went to the Vatican with three different tours: the Sistine Chapel, the Gardens, and the necropolis to see St. Peter's tomb.

There were a couple of hiccups in this perfectly planned itinerary. Each time, the travel specialist and her staff were immediately available and guided us through solutions, such as trying to get to the Colosseum during the Roman Marathon.

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Italy Trip Review: Piedmont, Langhe, Turin, Lake Como, 2 Weeks

Zicasso’s travel company was highly responsive and understanding of what we wanted to experience and used their expertise to steer us to the best people and locations possible.

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Italy Travel Review: Amalfi Coast, 1 Week

The details provided by Zicasso's travel company were excellent.

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