
Our 20 Best Italy Itineraries & Vacation Packages
The cradle of European civilization, Italy is a region that has conquered imaginations since the Ancient Roman Empire and one that has prospered under the Roman Catholic Church. Birthplace of the Renaissance, home to the highest number of UNESCO World Heritage Sites in the world, and a haven for food lovers who treasure the freshest seasonal produce coupled with a fine wine, it comes as no surprise that Italy has many travelers returning for a second and even a third visit.
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Let these itineraries inspire your personalized travel experience

10 Day Trip IdeaFrom $4,500
First-Time Traveler’s Tour of Italy: Venice, Florence, Rome

12 Day Trip IdeaFrom $11,600
Italian Adventure to Rome, Amalfi Coast and Sicily

8 Day Trip IdeaFrom $3,300
Joys of Rome and Southern Italy Itinerary for Seniors

21 Day Trip IdeaFrom $20,500
Fully Immersive Tour of Italy: Highlights and Hidden Gems

17 Day Trip IdeaFrom $7,500
Splendors of Italy 17-Day Tour

8 Day Trip IdeaFrom $3,600
Exploring Cinque Terre Itinerary: From Levanto to Santa Margherita
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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.

7 Day Trip IdeaFrom $2,600
7-Day Italian Culinary, Wine, and Gelato Making Tour

8 Day Trip IdeaFrom $2,900
Wine Connoisseur's Dream Tour of Tuscany

8 Day Trip IdeaFrom $2,900
Italy for Second Timers: Puglia and Amalfi Coast Itinerary

12 Day Trip IdeaFrom $11,700
Luxury Tour of Italy's Finest: Lake Como, Venice, Florence, Rome Itinerary

10 Day Trip IdeaFrom $4,500
Kid-Friendly Family Tour of Italy's Highlights
Reviews of Zicasso's Our 20 Best Italy Itineraries & Vacation Packages
Based on 2884 verified traveler reviews.
I have to begin by saying I've told everyone how pleased I am with Zicasso and the travel agent they recommended. I also have to say that I was very hesitant to book my trip with a company that I had only communicated with via email. Turns out I had nothing to worry about.
The initial response I received from my agent was immediate and continued right up until our actual trip while we were in Italy. I let her know where I wanted to go, what I wanted to see, told her I was interested in a mix of arranged tours and time on our own. She listened and also made great suggestions. I honestly can't say enough about how wonderful she was to work with, along with her co-worker.
They arranged for all our hotels, transportation and tours. Every driver and guide we had was top notch. They made a point of keeping us in small groups, sometimes only the two of us and the guide.
Our 19 day trip began in Venice where we were met at the airport and driven to a private water taxi. That driver walked us out of the boat and made sure we knew how to find our hotel. Our departure was just as seamless. A guide met us in our lobby, walked with us to the water taxi, came into the train station with us and explained the board to us, pointing out our train and track number.
We continued on to Verona, Cinque Terre, Tuscany, Florence, Naples, the Amalfi Coast and Rome. Since we weren't in any one place longer than three days it was extremely helpful to have guides, even for just a couple of hours to orient us, which saved us a lot of time. We had guides for a walking tour in Venice, a morning in Cinque Terre traveling with us between the villages, the Accademia in Florence, Pompeii, an Amalfi Coast drive and the Vatican in Rome. Every one of the them was passionate and proud and we learned so much. We had a car in Tuscany and saw many other places on our own, Lucca, Pisa, San Gimignano, Siena, Montalcino, Montepulciano. We stayed in Sorrento, spent one day on Capri and another full day on a tour to Positano, Amalfi and Ravello, which included a short boat ride along the coast. Spectacular. Our only tour in Rome was the Vatican but we saw all the other major sites on our own, taking the metro, bus, taxis and walking, lots of walking. It was the perfect mix of free time and arranged tours.
And, they also worked with our children who surprised us with a dinner in Venice for our anniversary after a gondola ride!
One great advantage to having your tour guide in the country you're visiting, you're in the same time zone. We had one mishap with a train and were able to talk to them right away. Other than that, everything worked liked clockwork.
I would definitely use them again and have told everyone I know what a wonderful job they did for us.
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We experienced a fabulous twelve night first trip ever to Europe staying in Rome, Sorrento, and Florence with day visits to Naples, Pompeii and Herculaneum, a drive with stops and photo-ops through the beautiful Amalfi coast villages to Ravello, and a day trip to historic Siena and San Gimignano through the Chianti region of Tuscany. Our travel consultant and her colleague at the company in Rome, proved to be perceptive to our interests, resourceful in finding spot-on solutions within our budget and patient professionals as we explored various itinerary options. Both women spoke and wrote english very well to thoughtfully help us plan our itinerary for three adults with private transportation and guides. Our private guides in Rome; in Pompeii and Herculaneum; in Naples; one a Canadian ex-pat in Florence; and in Siena, informed our discovery of each locale and its many treasures. We also did two small group tours. First, a farm/food tour near Sorrento with an incredibly informative and entertaining guide, and catacombs at Saint Sebastian with a nameless guide and small group of 9 during our Appian way visit and final full day in Rome. At times we were chaperoned in private vehicles with english speaking drivers knowledgeable of their territories. In Rome, in Naples, in the Bay of Naples Sorrento area, in Tuscany, and in Amalfi. We wouldn't hesitate to recommend this company to help others plan the vacation of a lifetime.
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We (family of 4 including two teenagers) had a wonderful trip to southern Italy the last two weeks of June: Sorrento, Naples, Matera, Polignano a Mare (Puglia region). With Sorrento as our base we saw Positano/Amalfi Coast, Capri and Pompeii. In Puglia we visited Ostuni, Alberobello and Lecce, went to a wine tasting (with great wine!), and visited two masserias: one for an olive oil tasting, and another with a pasta-making class. Our travel agent at at this company helped us to plan a great itinerary. She was very flexible and helped us keep within our budget, and the logistics she put together were flawless. I also felt she truly listened to what we wanted - even her first draft itinerary was very close to the mark. Highly recommended.
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We took this trip last year, and I realized when I came back to Zicasso to plan our next trip that I had never posted a review.
This was a 25th anniversary trip for my husband and me. We splurged on this trip. We wanted something special. We were overwhelmed by a trip that not only met, but far exceeded our expectations. Our Italy travel agent planned every detail and stayed in contact with us throughout our travels. She gave us a flip phone and called us shortly after we reached each destination to make sure everything was to our liking. And when we did run into a slight problem with our gondola ride in Venice, I was able to get in touch with our agent on a Sunday, and she took care of it immediately. Every driver and tour guide she set us up with was professional and well-informed about their part of the country. And they all spoke English very well. We felt pampered every step of the way.
Even with 2 weeks to spend in Italy, it felt like a whirlwind trip. Our agent managed to fit in everything we wanted to see and do and some things we hadn't even known we wanted: A gondola ride and a tour of St. Mark's in Venice; a guided trip to the Accademia to see the statue of David and to the Uffizi Gallery, as well as time to walk across the Ponte Vecchio in Florence; wine tasting in Tuscany, not only of Chianti but also Brunello di Montalcino (what a treat); visits to Siena, San Gimignano, Montepulciano, and others in the area; a guided tour of Pompeii; visits to Amalfi, Ravello, and an inland winery near the Amalfi coast; a private cooking class; guided tours of the Colosseum, the Forum, the Vatican Museum and St. Peter's Basilica.
My husband and I would wholeheartedly recommend this agent and her travel company to anyone who is planning a trip to Italy.
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Thanks for helping me organize my family (of 10 with diverse age from 15 to 63) trip to Italy, from Dec 17 to Dec 31. Whilst different member of my family have different expectation and requirement, I would like to comment you and your team on having planned an excellent trip that not only met each and everyone's interest and expectation but truly exceeded it.
Your planning have brought us to the lovely cities of Parma, Modena, Florence, Orvieto, Civita Di Bagnoregio, Naples, Rome, Venice, Cortina d'Amprezzo and back to our starting point Milan. Throughout the trip, we have a well balance itinerary that covered
- beautiful churches such as the Duomo in Milan, Rome, Florence,
- archeological site like Pompeii, Colosseum, Roman Forum, Pantheon, Pisa, Verona (learning more about romeo and Juliet)
- great local eating places (recommended by the guides you chose)
- lovely country side and unique sight in San Gimignano, Civita Di Bagnoregio, Orvieto, Lake Como,
- great gallery likes Uffizi, Academia
- Interesting activity such as Snow Mobile excursion in Cortina, Learning Cooking
- Shopping activities
With so much, yet your team immaculate planning never have us rushing from sight to sight, we were both able to enjoy and learn as much as we can of each sight and at times added more activities.
The team of guides you chose, have truly turn stone and history into exciting stories that the provided the group deeper understanding of the sights we visited and saw. Really like to thank each on of them like our guides in Florence, Pisa, San Gimignano, Orvieto and Civita Di Bagnoregio, Naples and Pompeii, Rome, Verona, Venice and Milan.
But most importantly, thank you for getting our driver, he truly ensure our comfort whilst driving steadily through jams on our way to Naple and snow storm on our way to Cortina d Amprezzo and also took very good care of us ensuring we know what to do where we have no guides and leaving us clear instruction when we needed help. He is truly a wonder.
I will definitely tell my friends heading to Italy about this company.... A wonderfully great experience.
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