Luxury Italy Family Vacation

Family on a luxury yacht in Sardinia, Italy.

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.

Countries Visited

Italy, Vatican City

Places Visited

Milan, Venice, Sardinia, Bologna, Florence, Rome, Pompeii, Vatican City

Suggested Duration

16 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Day 2

Venice - From Magnificent Milan to the City of Canals

Day 3

Venice - Exploring the Queen of the Adriatic

Day 4

Olbia - From the Mainland to the Islands

Day 5

Olbia - The Charms of Scenic Sardinia

Day 6

Olbia - A Journey Through Time and History

Day 7

Bologna - Turning to the World’s Oldest University Town

Day 8

Bologna - A Visit to Italy’s Famous Automakers

Day 9

Bologna - The Culinary Treasures of Bologna

Day 10

Bologna - Tricks of the Trade in an Italian Kitchen

Day 11

West to Tuscany’s Famous Capital

Day 12

Florence - Hitting the Highlights of the Birthplace of the Renaissance

Day 13

Rome - All Roads Lead to Rome

Day 14

Rome - A Guided Tour of Unforgettable Pompeii

Day 15

Rome - The West’s Greatest Empire and the World’s Smallest Country

Day 16

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)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

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.

4.9

Verified Traveler Reviews

Based on 1059 reviews

Italy Tour Review: Vatican, Colosseum, Roman Forum, Pompeii, Tuscany, Venice, Cheese-Making Experience, Cooking Class, 13 Nights

Zicasso's travel agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.

Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.

Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.

Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.

Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.

We travel a bunch and I would highly recommend using Zicasso's travel partner.

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Italy Family Vacation Review: Venice, Verona, Florence, Tuscany, Siena, Rome, Biking, Cooking, Wine Tasting, Olive Oil Experience, 10 Nights

Zicasso's travel company planned the most amazing trip to Venice, Verona, Florence, Tuscany, Siena, and Rome for our family of five. It was the best trip I've ever taken, and having all the details covered by them and plans and tickets sent to us via WhatsApp allowed us to really live in the moment and not have to think about what was next. I loved every second. I cannot wait to plan another trip to Italy to experience the southern half of the country.

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Switzerland, Italy Solo Vacation Review: Zurich, Lucerne, Interlaken, Zermatt, Lake Como, Venice, Florence, Sorrento, Amalfi, Rome, Skydiving, Gondola Ride, Amalfi Coast Cruise, Scenery, Nature, Local Cuisine, 3 Weeks

My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.

Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.

Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.

Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.

What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.

Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.

As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.

Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.

The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.

This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.

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Italy Tour Review: Rome, Florence, Venice, Private Tours, 12 Nights

Our recent trip to Rome, Florence, and Venice, planned by Zicasso’s travel specialist and her team, was nothing short of exceptional. Every detail was handled with care, precision, and an obvious commitment to excellence. The hotels were truly top rate, perfectly located, and impeccably chosen to enhance the experience of each city. The tour guides were extremely knowledgeable, engaging, and clearly passionate, adding depth and context that made each destination come alive.

What truly set this trip apart was the level of service. From seamless transfers to on-the-ground assistance, everything felt effortless. The recommendations and tips provided along the way were incredibly useful and allowed us to experience each city with confidence and ease. The assistants who helped guide us through logistics and navigation were attentive, professional, and reassuring, making the entire journey feel like true white-glove service from start to finish.

The travel specialist and her team exceeded every expectation. Their planning, responsiveness, and attention to detail transformed an already incredible itinerary into an unforgettable experience. I would recommend them without hesitation to anyone looking for a flawlessly executed, high-end travel experience.

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Italy Family Trip Review: Venice, Florence, Rome, Naples, Pompeii, Ferrara, Paestum, Cheese Sampling, Wine Tasting, Local Cuisine, History, 14-Night Tour

Our trip was a family one, two grandparents over 70, two parents and one adult son, one teenage girl, and one younger girl, 12. Three of us had been to Italy while the others had not. We wanted as complete a trip as we could in 14 days, so we included all the traditional places, Venice, Florence, Rome, and Naples/Pompeii. We spent three days in each and one day in Ferrara. While it was a lot for 14 days, we did not feel rushed.

What I like about Zicasso is they give you options to pick the best fit for your trip—we worked with two other agencies before we picked Zicasso’s travel partner. This travel partner took the time to understand our needs: three hotel rooms, all different in sizes, and tours and timing. Very important was the degree of coordination before the trip with the travel agent; she was available and knowledgeable, and took the time to adjust our needs. One of the best things about this travel partner was they used a van for all the travel, except from Rome to Naples. This was a much better option than the train for seven people and baggage.

During the trip, we were met on time by every driver and every guide. The hotels were excellent and the whole trip went well. When we had a delay on the train, the driver knew it and adjusted our pick-up.

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Italy Tour Review: Sorrento, Florence, Rome, Pompeii, Winery, Private Tours and Guides, 13 Nights

Zicasso’s travel specialist was a fantastic travel advisor. This tour operator helped us plan our perfect Italian vacation by listening to our desires, from wanting boutique hotels with a view to private tours. They secured transportation from Sorrento to Florence to Rome.

Our driver to the winery was exceptional. He went above and beyond to find a quaint restaurant that served my favorite meal: white-truffle pasta. We also had an amazing guide in Pompeii. He was very informative and even surprised us with his beautiful singing voice in the amphitheater inside Pompeii. This trip was magical. We could not have asked for a better organized, non-stress trip.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

30,000+ Verified Traveler Reviews