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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.

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Let these itineraries inspire your personalized travel experience

14 Day Trip IdeaFrom $6,300

Custom Cultural Italy Tour in 2 Weeks

Rome, Florence, Siena, San Gimignano, Chianti +2 more

14 Day Trip IdeaFrom $6,200

Luxury Italy Tour in 14 Days

Milan, Como, Venice, Florence, Pisa +19 more

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

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.

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More 14 Day Vacations Near Italy

4.9

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

Based on 5985 verified traveler reviews.

Italy Travel Review: Vatican, Rome, Wine Tasting, 9 Nights

We had a wonderful experience, from planning our trip with Zicasso's travel designer to experiencing all Italy had to offer. She and her team worked with us when we needed to have them step in on hotel accommodations at our beach resort.

Italy Travel Review: Heritage, Local Cuisine, 10 Nights

The hotels were in great locations within the city to be able to walk and see all the sites. The drivers we had were very professional and courteous. I would have liked to have a better platform to track the trip and the destinations. I have used a trip plans app before and it’s easy to use. I felt like the communication with our travel guide was minimal, but our overall trip was beautiful and memorable, and we will definitely be traveling again soon.

Italy Tour Review: Cooking Class, 1-Week Trip

Zicasso's travel designer listened to our desires and implemented those wishes. The trip was flawless. The accommodations, transportation, and guides were spot-on and within budget. We will certainly use the travel company for future trips.

Italy Travel Review: Taormina, Syracuse, Catania, Militello, Ragusa, Aci Castello, Modica, Mount Etna, Private Tour, Cooking Class, Boat Ride, 9 Nights

This was a superb trip that allowed us to combine personal visits to Taormina and Syracuse with a pre-planned group meeting in Catania. Planning and communication were excellent, supported by an app that let us easily view our itinerary, complete with phone numbers for the drivers, hotels, and the tour operator contacts.

The hotels were perfect! They were wonderfully located, with impeccable service in Taormina and Syracuse. Our excursions were private and diverse, and allowed us to combine culture, foodie interests, and free time. The guides were top-notch, knowledgeable, and flexible.

We especially loved seeing the smaller towns of Sicily; Militello, Ragusa, Aci Castello, and Modica. We even arrived in one small town during their annual festival.

We had a dedicated driver for our trip who was, himself, a treasure; always on time, always ready to adjust to changes, and a delightful personality.

This was such a good experience that we have selected Zicasso's tour operator to book another Italy trip next year.

Italy Vacation Review: Tuscany, Cooking Class, 4 Nights

This was a girls' trip of a lifetime! It was perfect from the start of planning until the end of the trip. Zicasso's travel experts were so flexible in planning and giving options. The experiences were all so unique, special, and local. We would never have been able to create this on our own. Also, during the trip, they were available 24/7 for any recommendations or help. I cannot say enough good things! This is my second time using Zicasso and I have told all my friends!

Italy Tour Review: 1 Week

We received great communication from Zicasso's travel specialist and wonderful hotel, tours, transportation, and guide arrangements.