
Italy Trip Planner
Whether you are searching for the most delicious fare, the finest art, or the grandest cities, Italy is full of experiences that will revitalize your senses. Zicasso’s Italian Trip Planner possesses a wide variety of authentic, Italian experiences, and our custom itineraries cultivate the opportunity for travelers of all ages and interests to find an Italian experience that is best suited for them. Inspiration starts here.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

14 Day Trip IdeaFrom $6,200
Iconic Italy: Fast-Paced Exploration from Venice to Sicily

12 Day Trip IdeaFrom $11,700
Best of Italy Vacation in 12 Days

8 Day Trip IdeaFrom $3,600
Soulful Italy: Umbria, The Marches, and Abruzzo Tour

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

12 Day Trip IdeaFrom $5,400
Honeymoon Highlights: Rome, Florence, Venice Tour
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.

12 Day Trip IdeaFrom $5,400
Family Trip to Italy: Nature, Ancient Temples, and Cuisine

7 Day Trip IdeaFrom $3,200
One Week in the Tuscan Countryside Tour

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

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

10 Day Trip IdeaFrom $4,500
Flavors of the Vine & Countryside: Exploring Italy’s Slow Food Movement Tour
More Trip Planners Near Italy
Reviews of Zicasso's Italy Trip Planner
Based on 2672 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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THE BEST VACATION EVER!!!!
I must admit that I was somewhat uncomfortable arranging a group tour to Italy with someone I communicated with only via the Internet and telephone. However, after my first communication with our agent -- I knew that she “had it.” She understood exactly what we wanted to do. She was right-on in both concept and execution.
Our ten-day adventure in Italy began with a private transfer with an English speaking local driver from the Rome airport to our fantastic 3 star boutique hotel located right in the historical center of Rome. During our three days in Rome, we had fantastic private tours of Ancient Rome, the Coliseum, and the Vatican Museums. Extremely knowledgeable, English-speaking guides led all of our tours. Sense of Italy had arranged for VIP, skip the line, priority entrance for all tours -- saving us from long waits in long lines.
After our busy 3 days in Rome, we departed via private van transfer from our hotel in Rome to the Chianti Region of Tuscany. The transfer included stops on the Val D’ Orcia to visit the amazing Villages of Montalcino and Montepulciano. The “light lunch” and wine tasting we enjoyed in Montalcino was one of the highlights of our trip. In Tuscany we stayed 7 Nights in a beautiful, historic villa located on one of the best wine estates of Chianti (Villa Le Corti near San Casciano) where we were met with a fantastic welcome dinner. During our time in Tuscany we were transported by private van from our villa to private tours of Siena, San Gimignano, Florence, Pisa and Lucca. On each of our stops we were met by knowledgeable English speaking guides that clearly were proud of the history of their country, and were anxious to share it. Interspersed in all of this activity were numerous exceptional meals with opportunities to taste (and drink) very fine Italian wines.
When we finally were forced to leave Italy, our agent arranged for private transport accommodating our varying departure times from the Florence airport and train station.
Thanks to this travel company and our agent for designing the perfect vacation for our group. The only complaint that I heard was that we ate too much — wow was all the food delicious. I really don’t know how she did it. All of the tours were great — the van drivers friendly and helpful, the guides knowledgeable, and the sites spectacular. Our stay in the villa was a great experience. We were treated royally everywhere. We all marveled at our agent's ability to get us, the vans, the guides, the food and wine, etc. all at the right place at the right time. She is a genius!!!!
Jeff E
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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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My husband and I, along with our 2 children (age 20 and 17), enjoyed a wonderful Italian vacation booked through Zicasso and this travel agency. Our travel consultants listened to my ideas and arranged for us a fantastic custom itinerary. They stayed within the budget allotted, offered choices for beautiful hotels and private tours, and made several revisions as per our request. We departed from New York on our 25th anniversary, and spent 10 days traveling the country within the month of November. This off-season time proved to be a great decision as reservations were easy to obtain, crowds were minimal (mostly all locals), and the weather was conducive for walking and sightseeing (average 60 degrees F). Transportation and the personal drivers were top notch; with Mercedes SUVs or minivans to take my family from Milan-Chianti-Florence-Verona-Venice and then the high speed train down to Rome. Accommodations arranged for us were phenomenal! We stayed in a 12th century castle in Chianti, in the heart of the city center in Florence, and near the Spanish Steps in Rome. The personal tour guides were friendly and knowledgable, and were happy to recommend eateries preferred by locals. All in all, everything was flawless. We plan to return some day to see the Amalfi coast, Positano and Capri. We would absolutely recommend these travel consultants, and the travel company team to anyone who is looking for a personalized Italian vacation.
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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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My husband and I just returned from a two-week vacation in Italy. With the help of Zicasso and our travel company, we were able to fit every wish into this short time.
We started out in Rome, then went on to Florence for some amazing history. We then traveled to the Tuscany and Chianti countryside for private cooking and wine experiences. We loved the small villages we explored and the little family-owned wineries and olive farms.
A highlight was staying in a bed and breakfast in Ponzano that overlooked the beautiful olive gardens and countryside. We explored the small villages of San Gimignano, Montepulciano, and Montalcino, and felt like we had discovered authentic local life.
The tail of our trip was spent in the beautiful Lake Como area, with a day trip to Lugano, Switzerland.
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