The Dolomites in Italy
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Luxury Italy Tours & Vacations

Italy is a beacon, beckoning to those in search of an immersive cultural experience. Be provided with the most exclusive access, from Milan’s fashion week to private dining experiences hosted by top-tier chefs. Elevate the quintessential Italian vacation to an entirely different level with Zicasso’s luxury Italy tours, where your travel dreams will be made a reality.

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Let these itineraries inspire your personalized travel experience

Val d'Orcia in Tuscany, Italy

12 Day Trip IdeaFrom $11,700

Best of Italy Vacation in 12 Days

Venice, Lake Garda, Florence, Rome, Amalfi Coast +5 more
Wine tasting tour in Tuscany, Italy

9 Day Trip IdeaFrom $8,800

Luxury Italy Wine Tour of the Top Regions

Piedmont, Lombardy, Chianti
The coast of Sorrento in Italy

12 Day Trip IdeaFrom $11,600

Italian Adventure to Rome, Amalfi Coast and Sicily

Rome, Sorrento, Capri, Amalfi, Positano +4 more
Couple in Florence, Italy.

10 Day Trip IdeaFrom $9,600

Italy Honeymoon Indulgence: Romance, Food, and Wine

Bologna, Florence, La Morra
Saint Peter Basilica in Rome at Christmas

14 Day Trip IdeaFrom $13,300

Christmas in Italy: 14-Day Luxury Celebration

Venice, Rome, Siena, Florence
Family on a luxury yacht in Sardinia, Italy.

16 Day Trip IdeaFrom $15,600

Luxury Italy Family Vacation

Milan, Venice, Sardinia, Bologna, Florence +3 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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Sforza Castle Castello Sforzesco is one of the symbols of Milan, Italy

11 Day Trip IdeaFrom $9,900

High-End Northern Italy Tour: Venice, Lake Garda, Milan

Venice, Lake Garda, Milan, Verona, Mantova
Medieval city of Matera in Southern Italy during a sunset

12 Day Trip IdeaFrom $9,400

Exclusive Southern Italy Vacation: Sorrento, Matera, Ostuni

Sorrento, Capri, Herculaneum, Paestum, Matera +7 more
Riomaggiore, Cinque Terre, Italy.

21 Day Trip IdeaFrom $20,500

Fully Immersive Tour of Italy: Highlights and Hidden Gems

Venice, Bologna, Cinque Terre, Siena, Sorrento +2 more
Runway model in a red dress at a fashion show. Credit: Ahmad Ardity

10 Day Trip IdeaFrom $12,900

Italy in Vogue: Exclusive Access to Milan Fashion Week & Italian Style

Milan, Tuscany, Florence
Photo courtesy of Museo Lamborghini

10 Day Trip IdeaFrom $9,800

Prestige & Passion of Italy Tour: The Italian Racing Tradition

Emilia-Romagna, Modena, Bologna, Maranello
The dome ceiling inside Santa Maria del Fiore in Florence, Italy.

10 Day Trip IdeaFrom $9,800

Italy: The Gold Standard Tour

Tuscany, Bologna, Florence, Ponte Vecchio, Uffizi Gallery +2 more

4.9

Reviews of Zicasso's Luxury Italy Tours & Vacations

Based on 2679 verified traveler reviews.

Review: Italy Family Vacation, Rome, Tuscany, Florence, Amalfi Coast, Sorrento, Positano, Pompeii, Pisa, Vatican Papal Mass

Our family of five just got back from the most wonderful vacation in Tuscany and Rome.  Our agent crafted a set of amazing experiences for our family from the private tour guides to Florence, Pisa and Lucca; a private wine tasting lunch at the Capannelle Winery and vineyards in Chianti; tickets to the Papal mass at the Vatican; to a tour beneath the church of San Clemente to see the excavations of a byzantine and then a Roman street neighborhood; a day excursion to the Amalfi coast to visit Positano, Sorrento and Pompeii; and more! Our agent and the guides found excellent restaurants from a simple salumeria where the locals ate to some high end restaurants.  The hotels were right in the center of Florence – on the piazza della Repubblica - and Rome – between the Piazza del Popolo and the Spanish Steps.  Our agent was attentive to our plans and made excellent suggestions.  Everything went extremely smoothly.  All the guides drivers were very friendly, spoke English and were very knowledgeable about art, history and the local culture.  We saw so much every day because everything was so well planned.  Simply the best travel experience ever!

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Luxury Anniversary Vacation Review: Italy, Florence, Venice, Amalfi Coast, Cinque Terre, Tuscany, Verona, Naples, Vatican, Pompeii

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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Review: Luxury Italy Family Vacation, Rome, Venice, Florence, Tuscany, Chianti, Verona, Milan

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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Travel Review: Italy Trip, Rome, Sorrento, Florence, Naples, Pompeii, Herculaneum, Ravello, Siena, San Gimignano, Farm & Food Tour

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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Italy Tour Review: Venice, Sienna, San Gimignano, Rome, Revello, Amalfi, Pizza Making Class, Winery
TRIP OF A LIFETIME!!! We have wanted to travel to Italy for a long time and have encountered many different tour groups/agencies. We were going back and forth for a while trying to figure out what our *must sees* were, how much time we should spend in one place, and Transportation (do we want to drive by in a bus and just wave at the sights or actually be able to get out and learn/experience Italy with just our small group). When talking on zoom with the travel agent (many many and did I say many times) she was able to provide so much knowledge and listened to what we wanted to do. We were able to go over the itinerary and change things with them over zoom. It was nice to have the agency based out of Italy because they would know best (where to stay, what to visit, where to eat). They created a group chat before we left for our trip and we were able to contact them along our journey with any questions we had. The whole team (including the tour guides and drivers) were amazing and we are so thankful for all the work they put in to make our trip amazing! We were provided first-class treatment every day,  our transfers, tour guides, and accommodations were truly amazing!! As for the trip, we had two weeks to travel around Italy, starting in Venice, Florence, Rome, and the Amalfi coast. From Florence we were able to take a couple of day trips to some really cool and historic towns, We visited Sienna and San Gimignano and we also visited a boutique winery in the Chianti region. In Rome, we visited the Vatican with our private tour guide, We also went to the colosseum the next day with her. She timed it so nicely that we were the first ones in the colosseum and it was absolutely breathtaking. Later on, in Rome, we had a pizza-making class with a small group of people which was a really fun experience. Lastly, we headed to the Amalfi coast making stops in Sorrento, Positano, Revello, and of course Amalfi. Absolutely stunning! And the view from our hotel room was even better, looking right over the Amalfi coast. Truly Beautiful! 

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Luxury Italy Family Vacation Review: Rome, Venice, Pisa, Assisi, Florence Biking, Amalfi Coast Boat Tour, Monte Cassino

                Planning a trip overseas with young children can be overwhelming when you don’t know all of the customs, the area, or how to get your little one safely from one place to the next. For those reasons, we considered a group tour of Italy for our first trip, but they just seemed to all be designed in the same cookie cutter fashion and without the kind of flexibility we hoped to enjoy. Thankfully we found our way to our agent with this Italy travel company who put together a custom itinerary that truly enabled us to experience several parts of this beautiful country—Venice, Florence, Rome, and The Amalfi Coast. From the individualized planning, the well-coordinated transportation, the lovely accommodations, knowledgeable guides, unique experiences, and especially the little details such as a local cell phone pre-loaded with all of the numbers and documents we would need during our trip, she went above and beyond in designing a trip that was unforgettable in all of the right ways. For these reasons and those discussed below, I enthusiastically recommend this company to anyone planning an Italian vacation.

                From the start, we worked with several travel agents at different companies, trying to design an itinerary that fit our needs, interests, and budget. Our agent was the only one that seemed to truly listen to us and select not only hotels and transportation that would accommodate a toddler, but also experiences that would include her and were unique to our interests, even including a trip to my family’s hometown that was far off of the beaten path. She also offered us advice on best ways to get around with children in each city, provided a list of restaurants that would welcome our daughter, and, when I unexpectedly learned I was expecting another child, she offered to let everyone involved with our trip know of any special needs or food aversions I might have. While the individualized service and transportation would seem to come with a hefty price tag, the cost was actually the same as the hokey bus tours and very competitive with all of the other offers from travel agents we received, making the choice of this company a no brainer.

                And the transportation alone was well worth the price. Everything was so beautifully choreographed: for instance, we walked out of our hotel in Venice and boarded a water taxi, which took us to a Mercedes van with child seat installed that was waiting for us, which took us to the train station where we boarded and took our first class seats.  All of our transportation ran this smoothly, and we know there is no way we could have seen everything we did see had we tried to navigate Italy on our own. We always rode in luxury vehicles. Some were even equipped with DVD players for our little one. The drivers were excellent. Each English speaking driver was waiting for us at the airport or train station with a sign, handled all of our luggage, and acted as our first guides to each city as well. Additionally none of them pushed for any of the tips they definitely earned.

                The hotels also exceeded our expectations. All of the accommodations were well-located, four star properties, and were the same hotels our agent included in her original price quote. When we were planning our trip, people kept telling us of the small quarters you’re forced to stay in in Italy and other European cities, but we did not find this to prove true in the hotels our agent chose for us. Every room had at least a queen size bed and a full size bed for our toddler, a sitting area, as well as a decent sized bathroom—one even had two bathrooms, another even had a bathtub, which is quite rare in Italy. Each hotel offered an exceptional free breakfast with a mixture of hot and cold entre choices and fresh local produce. Plus every hotel offered something different. In Venice we stayed at a boutique hotel with a long history that was in an area all of the locals agreed had the best restaurants and cafes. It had a lovely courtyard with a pool. In Florence we stayed in a sleek, modern hotel that featured a rooftop pool and bar with stunning views of the city. In Rome we stayed at a modern boutique hotel that greeted our child with a t-shirt, coloring book, and candies. And finally in Positano we stayed in a hotel that had terraces overlooking the bay and city, a pool that looked out to the water and mountains, and an excellent restaurant.  The hotel staff at each place was quite friendly, and I doubt we could have selected better places on our own.

                All of our local guides had specialized knowledge that made them an excellent fit for the service they provided. In Rome we visited the ancient sites with a sculptor who spent his childhood at the ruins with his father, a famous archeologist involved in the digs and study of the ruins.  In Venice we got to know the city by spending the day walking and boating with a woman who spent nearly her entire life there, who gave us excellent recommendations for restaurants and things to do, and knew almost each person we passed. Similarly in Pisa, we were introduced to the city by a woman who lived there and whose husband operated a local winery. They were all so knowledgeable and friendly, and having them to ourselves for much of the day was invaluable, as we were able to ask questions and visit some places not accessible to large groups.

                Once we were introduced to the city, our agent also planned unique experiences to help us experience the place. We toured Venice by water. We biked our way through the narrow streets and beautiful countryside of Florence. We toured a winery and had a private six course lunch with wine pairings. We let our toddler run through an amazing Sculpture Park in Chianti.  We shopped, cooked, and dined with a chef in Rome. We sampled foods at specialized eateries in a neighborhood that pre-dates the Coliseum. We visited the abbey at Monte Cassino, rebuilt after being destroyed during WWII. And we travelled the entire Amalfi Coast by boat, visiting the Emerald Grotto, the Blue Grotto, swimming in caves, and enjoying Positano, Amalfi, and Capri. In two weeks we saw, experienced, and tasted so much that we will continue to relive this trip for a lifetime.

                In all ways, as I hope is clear, this trip was exceptional because of our agent's hard work and the work of all at our travel company. This showed not only in the ways already described, but also in all of the small details. We were greeted upon arrival with a welcome package and were given a phone that had all of our tickets, our itinerary, and everyone’s phone number loaded onto it. Our agent checked in with us periodically while we were there and made it clear that we could call at any time if we had questions, concerns, or if something was not up to par. When our boat tour was late, for instance, she called to change our dinner reservations. And she even educated us about some Italian customs before we arrived.

                A trip like this one is a financial investment for many of us, and I know from experience that putting your trust and your hard-earned money into the hands of someone you only communicate with via email or phone is scary. But believe me, if you choose this company, you will not be making a poor decision. There is literally nothing more I could have asked for, no other way this trip could have been more spectacular, and no better way I could have spent every one of my pennies. Thank you to our agent for making us the envy of all of our Facebook friends, for truly making this an awesome family vacation, and for making one of my ultimate dreams come true.

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