Luxury Italy Family Vacation

What to expect on this itinerary
From the pleasures of high culture to the joys of adventure, this 16-day luxury Italy family vacation offers something for all ages. Taste buds will revel in the joys of Bologna, eyes will feast upon the immaculate detail of the Sistine Chapel, and the beauty of the Mediterranean sunlight will shine brightly. No matter your preference, there is something in Italy for everyone in the family.
Customizable Itinerary
Milan - Touching Down on the Peninsula
You land this morning in Malpensa Airport, where a personal driver will be waiting to take you into the heart of incredible Milan, right to the door of the hotel. This afternoon, explore the many attractions of Milan, from the city’s amazing Duomo, a Gothic marvel that is one of the largest churches in Europe, to the boutiques of the world’s greatest designers that line the streets of this world fashion capital. The Galleria Vittorio Emanuele is one of the most upscale malls on the planet, and more astounding boutiques can be found at the well-known Quadrilatero. Dinner this evening can be at one of the city’s fine restaurants, but be sure to save some room because there's gelato around nearly every corner.
What's Included:
Venice - From Magnificent Milan to the City of Canals
Venice - Exploring the Queen of the Adriatic
Olbia - From the Mainland to the Islands
Olbia - The Charms of Scenic Sardinia
Olbia - A Journey Through Time and History
Bologna - Turning to the World’s Oldest University Town
Bologna - A Visit to Italy’s Famous Automakers
Bologna - The Culinary Treasures of Bologna
Bologna - Tricks of the Trade in an Italian Kitchen
West to Tuscany’s Famous Capital
Florence - Hitting the Highlights of the Birthplace of the Renaissance
Rome - All Roads Lead to Rome
Rome - A Guided Tour of Unforgettable Pompeii
Rome - The West’s Greatest Empire and the World’s Smallest Country
Saying Goodbye to Enchanting Italy
Trip Highlights
- Discover the many attractions of marvelous Milan, like the city’s immense and impressive Duomo and one of the best fashion scenes in the world
- Feel yourself be taken in by the irresistible attractions of Venice, one of the world’s most unique and romantic cities, filled with charm and verve from the Piazza San Marco to the glassblowers of Murano
- Visit oft-overlooked Sardinia, one of the oldest areas in Italy and the site of a rich and diverse historical, social and cultural scene
- Stroll the campus at the University of Bologna – the oldest institution of higher learning on the planet – before learning the finer points of fine Italian food at a renowned pasta maker in Italy’s culinary capital
- Get your gearhead fix and visit the factories of Ferrari, Lamborghini, Maserati, or any one of a number of fine Italian automakers that riddle north central Italy
- Walk the banks of the Arno and the notorious streets of Florence, the center of the art world for a century and one of Italy’s favorite vacation spots, filled with fun-loving people and a carefree atmosphere from the Ponte Vecchio to the spectacular Duomo
- Live up the incomparable history of regal Rome, the center of an Empire and a faith, the home to the Trevi Fountain, the Sistine Chapel, and some of the best restaurants and hotels in the country
- Make a day trip to mesmerizing Pompeii, where you’ll encounter the past in a way that you never have before
Starting Price
$15,600 per person (excluding international flights)
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 967 reviews
We've taken many family vacations over the years, but we all agreed this was the best one yet!
The team at Zicasso’s travel company did an exceptional job tailoring the perfect trip for our family. Every detail was thoughtfully planned, making the entire experience seamless and truly enjoyable from start to finish.
We had wonderful drives and knowledgeable, engaging tour guides who made each destination come to life. Some of our favorite highlights include a hands-on cooking class in Florence, exploring the beautiful Tuscan countryside, and having effortless access to iconic sites like the Vatican and the Colosseum.
The experiences were unforgettable, from the best food tour in Rome to a fun and unique golf-cart tour through the city. We also loved visiting a Parmigiano-Reggiano factory and a Parma ham producer, along with an extra-special stop at the Ferrari Museum that was such a memorable surprise.
Every moment felt thoughtfully curated and we came home with incredible memories that we will cherish for years to come. We highly recommend the travel company to anyone looking for a truly personalized and exceptional travel experience.
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We had the absolute best vacation and loved working with Zicasso’s travel specialist. The trip exceeded our expectations and everything was so easy on our end. Our drivers were fantastic and always on time.
Our guides for private tours of Pompeii and the Vatican Museums (including the Sistine Chapel and St. Peter's Basilica) were knowledgeable, friendly, spoke excellent English, and we never had to wait in extended queues.
The hotels selected worked perfectly for our family, with wonderful locations in Sorrento and Rome.
Our travel specialist was always quick to reply to our questions and truly planned a vacation we will never forget. We will use this her again when we return!
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When we decided to plan a family trip to Italy, I did some research and found Zicasso. They were very highly rated, and we reached out to them. Zicasso’s travel agent responded very quickly. She was friendly, professional, and asked us questions to ensure she knew what we were looking for in our trip. The travel agent planned an exceptional family vacation for us with a customized itinerary that included traveling to Rome, Siena, Florence, and ending in Venice. She tailored our trip to include private transfers from the airport to the hotels, as well as traveling city to city.
Each hotel had an excellent location that allowed us to easily walk and explore. The hotels were beautiful, clean, and comfortable, each with impeccable service.
They set us up with private tour guides, who not only allowed us to skip the lines to major attractions, but also personalized the tour so we were able to spend time viewing the things that were important to us. The guides were friendly, informative and engaging.
Every aspect was meticulously curated and the travel company checked in with me via a messaging app daily to share the next day’s itinerary. They were always available if we had any questions or if any issue arose, which never did because of how well they planned everything. I reached out to them asking if they could please make a dinner reservation for me and they were quick to secure that for us.
I would highly recommend this travel company and will definitely use them again in the future.
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We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.
The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.
The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.
One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.
Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.
While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!
Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.
Every experience felt personal, meaningful, and special.
This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!
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Zicasso's travel specialists did a magnificent job planning our itinerary to Rome, Florence, Bologna, and Venice. Our hotels were all beautiful and perfectly located. We really loved having luxury vehicles to bring us everywhere instead of having to get a taxi. It made a huge difference in ease and comfort, plus all the drivers were so nice and knowledgeable. The tours we went on were all enjoyable.
They also provided restaurant lists for each location. Of course, the best part was that we got married in Capri 20 years ago and this was our anniversary trip to bring our daughters with us and renew our vows together. They planned a lovely ceremony in a palace located on the Grand Canal, with a gorgeous private garden. It exceeded our expectations and ended our trip with a memory that will last forever!
We were sad to leave and can’t wait to go back, and will absolutely use this travel specialist and his crew again.
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Our family of six just returned from the trip of a lifetime and we owe it all to our incredible Zicasso travel specialist. Every detail was thoughtfully planned, allowing us to simply relax, explore, and make unforgettable memories together.
Our journey began in Rome, where we stayed in beautiful hotels and were greeted by professional, reliable drivers who made every transfer seamless. From there, we traveled south by train to experience Mount Vesuvius, a truly breathtaking day that combined history, adventure, and spectacular views. Next came the Amalfi Coast, where we stayed in a stunning waterfront hotel. Waking up to the beauty of the Mediterranean each morning felt like something out of a dream. Every recommendation was perfect, from the accommodations to the transportation and, of course, the local restaurants.
One of the most meaningful parts of our journey was traveling to Moliterno, the hometown of my wife's family. Visiting the place where her family story began was an emotional and unforgettable experience. Our private driver made the journey comfortable and enjoyable, allowing us to fully appreciate the beautiful Italian countryside. From there, we continued to the ancient city of Matera, where we spent several incredible days exploring one of the most fascinating and beautiful places we've ever visited. Finally, we departed through Bari, enjoying one last glimpse of Italy's stunning Adriatic coast before heading home.
Throughout the entire trip, every hotel was exceptional, every driver was punctual and courteous, and every transition was effortless. The itinerary struck the perfect balance between iconic destinations, hidden gems, relaxation, and meaningful family experiences.
This wasn't just a vacation. It was a journey our family will treasure for the rest of our lives. We cannot thank our travel specialist enough for creating such a seamless, personalized, and unforgettable experience. If you're looking for someone who truly listens, plans with care, and delivers beyond expectations, look no further. We give our highest recommendation and are already dreaming about our next adventure together.
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