Italy Family Vacation for First Timers

What to expect on this itinerary
Immerse yourself in Italy with unique and interactive experiences at every turn. Travel through Italy’s heartland with stops in bustling, metropolitan cities and countryside estates before walking the cobblestone avenues of ancient gladiators, sailing down gentle waterways, and basking in the Tuscan sunshine. The architectural and artistic masterpieces, colorful frescoes, and gorgeous mosaics will give you something to take your breath away before you master the art of Italian cuisine and learn the techniques behind the perfect pizza, creamy gelato, and chocolate delights. Cathedrals, castles, museums, and monuments are waiting to be explored, and expert guidance in addition to customized experiences at each location make this luxurious, 9-day adventure through Italy the perfect family break.
Customizable Itinerary
Rome – Exploring Ancient Rome
You will land in Rome and immediately dive into the ancient world. Rome is the perfect place to begin your tour of Italy because it is both the country’s ancient and modern-day capital. You will be impressed by the vast array of ruins and relics, marvel at how cobblestone streets end at dramatic monuments like the Colosseum, and be provided with the opportunity to shop and stroll along famed avenues, dining in small establishments and on regional Italian specialties. Rome is the perfect introduction to Italy because it has something for every member of your family to enjoy. Your private driver will greet you at the arrivals area of Fiumicino Airport and whisk you away to your centrally located accommodation.
After a brief stop for a coffee and pastry, it will be time to harness your energy and hit the ground running. No trip to Rome is complete without visiting the Colosseum. An ancient gathering place and the largest amphitheater that has ever built, this is where riveting tales of gladiatorial fights and battle reenactments will keep you enthralled. Your private guide will be ready to tailor your exclusive tour to your family’s interests and guide you around the site as both an expert and as an actor, bringing to life the history of this location in an exciting way. Tales of gladiator flights, roaring crowds, and wild animals will spark your imagination and paint a picture of what an event would be like here among the sea of spectators. To fully immerse yourself in the experience, you will take a family photo with one of the many costumed gladiators outside of the venue.
You will then enjoy a refreshing beverage or icy granita, which is a frozen dessert, to cool off and calm down after your exciting Coliseum experience. Then, you will venture across the street to the Roman Forum, which was the center of day-to-day life in Ancient Rome. Together with your private guide, you will get involved in a hands-on archeological tour complete with a dig. You will work alongside a professional archeologist on an excavation, which will be the perfect way to uncover the longstanding history of Ancient Rome. You will then marvel at the mosaics and structures that have made their mark on this place for centuries.
What's Included:
Central Italy – Countryside Retreat
Perugia – Crazy for Chocolate
Florence – Highlights of the Historic Center
Florence – Palaces & Pizza
Turin – National Cinema Museum & Eataly
Milan – Turin's National Automobile Museum
Milan - Italy’s Largest Cathedral & Largest Stadium
Milan – Depart for Home
Trip Highlights
- Dig in and get your hands dirty at an archeological excavation at the Roman Forum
- Lounge poolside at a private estate that is nestled in the rolling hills of Umbria
- Invent and indulge in chocolate creations at the Perugina House of Chocolate
- Admire the Tuscan sunset in a Florentine Gondola on the Arno River
- Master the art of the perfect pizza with a private chef in Florence
- Explore the massive flagship Eataly location, where you will taste Italian favorites from every region
- Learn about the evolution of the automobile industry at the National Automobile Museum
- Marvel at the largest cathedral and stadium in Milan, Italy
Detailed Description
Italy has something every member of the family will enjoy. A perfect combination of old-world charm and modern comforts, Italy will wow you with its majestic scenery, cuisine, and history. This family-focused experience will show you the best of what Italy has to offer from the capital of Rome to the bustling Northern hub of Milan. Interactive adventures and expert guides along the way will take your trip over the top and allow adults and children alike to develop an appreciation of the sites, history, and culture of Italy.
Your trip will begin in Rome, where you will delve into the world of ancient gladiators. No trip to Rome would be complete without a visit to the Coliseum, and your private guide will bring this amphitheater to life for you and your family with tales of riveting gladiator matches. The impressive, intact ruins of the Roman Forum next door will continue to paint a vivid picture of day-to-day ancient Rome. You will take part in an excavation with a professional archeologist, where each member of your family can uncover treasures from the past.
After a busy stay in Rome, it will be time to revel in the height of relaxation at a private, countryside estate in Umbria. This home away from home will be yours for the next few days, so you can leisurely soak up the Tuscan sun, cycle along the winding country roads, and swim in the crystal waters of your private pool. Hands-on activities at this working farm will keep every member of your family occupied and enthralled, and a day trip to the Umbrian capital of Perugia and its famous chocolate factory will be on your schedule, which is where you will see how chocolate is made. Afterward, you will create exclusive creations of your own.
After a rejuvenating stay in the Umbrian countryside, it will be time to venture to the Tuscan capital of Florence. Its candy-colored cathedral will invite you inside to view its intricate interior and its dome that will be the perfect viewpoint to look out over the burnt orange tiled rooftops of the city. Florence has no shortage of palaces and manicured gardens to explore, and you will marvel at the ornate dwellings of the courtiers. After indulging in many Italian culinary specialties, you and your family will be provided with the opportunity, in Florence, to learn the art of Italian cooking with lessons in pizza and gelato making.
Departing from the heart of Italy, you will explore the country’s vibrant north, which will have a distinctly different feel to the places that you have visited thus far. Turin is filled with interactive experiences, and the National Cinema Museum, National Automobile Museum, and flagship Eataly location are just a few of these unique and exciting destinations that you can enjoy. Milan has some of the biggest and best landmarks in Italy, including the country’s largest cathedral and stadium, where you can feel small among these architectural behemoths. With so many beautiful locations to enjoy, this luxurious, 9-day tour of Italy covers the perfect highlights to introduce you and your family to intoxicating Italy.
Italy is a region unlike any other; learn more by seeing how our partner Italy tour operators can personalize the experience for you.
Starting Price
$4,100 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
Verified Traveler Reviews
Based on 1408 reviews
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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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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My wife and I recently returned from our first trip to Italy and want to highly recommend Zicasso's travel specialist and her company for creating the perfect vacation for us. It was a two-month process of back and forth, but no matter what we asked of her, she delivered several options.
We had a perfect mix of historical Florence and its museums, and wonderful restaurants, and the Tuscany and Umbria countryside experience. And on our first day, when our flight into Florence got diverted to Milan, we had the peace of mind that our travel specialist was there to help with her much appreciated support.
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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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My wife and I recently returned from a memorable trip to Central and Northern Italy, expertly organized by the tour company. We began planning our journey a year in advance, knowing we wanted to spend at least four days in Florence, but otherwise uncertain about the best way to structure our itinerary. After discovering the tour company through the Zicasso website—whose services we have appreciated in trips to the Netherlands and New Zealand—we felt confident in their recommendation.
From our first interaction, the tour company impressed us with their professionalism, in-depth knowledge, and genuine commitment to crafting our ideal vacation. Throughout the planning process, their team was attentive and flexible, fine-tuning our itinerary to include the most rewarding sites and experiences. Once our trip began, every detail was meticulously managed, from arranging drivers and guides to securing train tickets and accommodations.
Upon our arrival in Rome, we were greeted by a courteous and professional driver who ensured a seamless start to our adventure in Perugia. Throughout the trip, we enjoyed excellent hotels, reliable transportation in comfortable vehicles, and well-coordinated entry to museums and major attractions. The tour company also provided thoughtful dining recommendations that enhanced our overall experience.
What stood out most was their proactive communication. For example, when unforeseen changes occurred with our private boat tour on Lake Garda, they promptly notified us by both email and a written note delivered to our hotel room, preventing any confusion. Their attention to detail gave us complete peace of mind; we did not need to contact them during our travels, as all arrangements ran smoothly.
We are deeply appreciative of the tour company’s dedication and highly recommend their services to anyone seeking a carefully curated and worry-free Italian vacation.
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Kudos to Zicasso’s tour operator! This is our second time using them, and they didn’t disappoint us. They had to deal with two families, seven in all, all adults, with two separate trips. One trip for all seven to Rome and Florence. Two for Naples and Ischia.
The apartment in Rome was in a good location for us, as we usually stay near there. The only problem I found in this apartment was the smaller unit had a step down into the living room. The floors are dark, and the step needs to be highlighted so one remembers to step down. Several of us kept missing it, and luckily no one fell. Other than that, it was a nice apartment.
In Florence, our apartment was perfect. My husband and I would stay there again; however, it has four bedrooms, four baths, a nice kitchen, and a large living room, so it would be a little big for two people. It was perfect for families. It is on the third floor.
Since my husband and I have been to Rome and Florence many times, we did not have too many requests for tours. My cousin and her family were first-time visitors. I suggested a tour of the Vatican Museums, Ancient Rome, the Accademia Gallery, the Duomo Skywalk, a private tour of the Uffizi Gallery, the Vasari Corridor, and the Boboli Gardens. In Rome, all seven of us did a golf cart ride at night, which seemed to be a big hit. We also had a wine tasting and olive oil sampling in Chianti, which was very nice.
At one point, we thought we were going to have a wedding proposal. A place was planned for the proposal at one of the wineries. Unfortunately, the groom-to-be decided not to do it there since the future bride’s parents would not be there. I felt bad with all the work the travel company did to make this day special for the couple.
Since we were two families, all adults, sharing vacation rentals, the tour operator found two apartments to meet our needs. All of our drivers and guides were on time and very knowledgeable.
We made some last-minute changes on our trip from Florence to Ischia. Changes to the train tickets were made, but we were asked to check with the ferry service to see if they could take us earlier. Our driver went with us to the ticket office and was able to exchange our ferry tickets. Then we notified our travel agent, so they could call the hotel to send our driver earlier than planned.
We have used this tour operator before and would highly recommend them. The hotels they selected were excellent. We stayed at our hotel in Naples last year and asked for the same hotel again. The views were fantastic from our room, and the rooftop bar had views of Mount Vesuvius and the Bay of Naples. The staff were superb, and there was a wonderful breakfast.
We also asked for the same hotel in Ischia, but that hotel closed earlier this year. Another property was selected, our resort in Ischia. Unfortunately, we did not get a chance to use the spa this time, but the hotel had beautiful views from the restaurant, terrace, and our room. Both hotels were beautiful, and the staff were very attentive. Our resort in Ischia was not far from Ischia Porto. A bus stop was a short walk away, and the return stop was right in front of the hotel. The food and drinks were great, and we even walked into town one night, which took about 15 minutes.
I can’t wait to use the travel company again next year.
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