
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

14 Day Trip IdeaFrom $6,300
Custom Cultural Italy Tour in 2 Weeks

14 Day Trip IdeaFrom $6,300
An Unforgettable Honeymoon in Italy

14 Day Trip IdeaFrom $5,700
Northern Italy to Sicily: Italy Tour for Second Timers

14 Day Trip IdeaFrom $6,300
Amazing 14-Day Italy Itinerary with Capri

14 Day Trip IdeaFrom $6,300
Italy Tour of the Most Beautiful Towns & Villages
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
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.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.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.
More 14 Day Vacations Near Italy
Reviews of Zicasso's 14 Day Italy Itineraries & Vacation Packages
Based on 6093 verified traveler reviews.
We had a wonderful honeymoon in Italy! It was easy to coordinate with Zicasso’s travel specialist; she heard what we were interested in doing and seeing, and she planned a seamless vacation. The travel from point to point was easy, we had knowledgeable drivers and guides as we visited new places, and the hotel and restaurant recommendations all led us to perfect spots we wouldn't have found on our own. We had a great time in Rome and Florence, and in the countryside in Tuscany, and would absolutely consider Zicasso again for future trips.
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The trip was excellent. Zicasso’s tour operator handled our special request and situation very well. They were very responsive and helpful.
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Zicasso's was a great company to work with for our trip to Italy. Everyone replied promptly to questions or concerns. We liked the suggested tours. Most of the guides were very engaging and easy to understand.
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The tour company did everything we agreed upon.
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Zicasso’s tour operator was superb! Their communication, understanding of our requests, and planning were excellent. They made our first trip to Italy unforgettable.
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Zicasso’s travel specialist did a wonderful job at listening to what we were looking for in our trip and the experiences we would like to incorporate. Her recommendations were spot-on! All of the tours, guides, cooking classes, and drivers were excellent. All details were taken care of and we had nothing to worry about but enjoying our vacation.
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