Wonders of Italy Family-Friendly Tour: Rome, Florence, Venice and More

When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.

Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.

Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.

A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.

Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.

When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.

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.

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.

This was my third customized trip with Zicasso. I previously worked with Zicasso to plan and take mother-daughter trips to Iceland and Croatia. They are the perfect company to help your dreams for a personally unique adventure come true!

This time, I traveled with my daughter, son, and daughter-in-law to Italy. My hope was for my daughter and son to see the towns where their great-grandfather and great-grandmother emigrated from in the Abruzzo region, in the towns of Roccamontepiano and Bugnara. My research had an address for where their great-grandfather was born. Our driver found the address and we took photos of us standing in front of the house, which could now be considered a real fixer-upper. Just the same, it was a moment never to be forgotten. Thank you to our driver and his wealth of information!

Our home base was in Pescara, where we enjoyed a walk on the beach, excellent local cuisine at a local restaurant, and seafood at another local restaurant. These were recommended by our local travel agent and were clearly favorites of the locals.

We had a wonderful tour in Chieti, an historic and cultural gem, with our guide. She too was a gem of a guide!

We then traveled to Venice, which was far less crowded with tourists than in the high season. Upon arrival, a private gondola ride during dusk and at sunset was a surreal way to be welcomed to this beautiful city.

The next day we had a magnificent tour of St. Mark's Basilica and Doge's Palace. Our guide was so engaging and knowledgeable, and eager to share ideas about other things to see while in Venice. We followed our tour with lunch at a historic restaurant, home to the invention of the Bellini. Yum! After lunch, we took the elevator to the top of the tower across from the basilica, with its spectacular panoramic view of the city and surrounding islands. Then our group splintered off—two of us did a Grand Canal boat ride and the other two headed to the isle of Murano to search for glass souvenir treasures.

Our next stop was Lake Como, with a one-hour unexpected stop in Verona. Thank you to our driver for suggesting the stop! Who knew there was a Roman arena and some to-die-for hot chocolate in Verona!

Then off to Lake Como. We had time before we could check in to our hotel, so we did a walkabout to acquaint ourselves with the city. We took a ride on the funicular for another delightful panoramic view and enjoyed cocktails while surveying the lake and city below. That evening, we traveled up into the mountains and had a marvelous meal at a mountain trattoria. We were just us and one other couple in the restaurant, and we watched the chef prepare our local food specialties from our table in front of the wood-burning fireplace. The mantel was adorned with trophies and photos of the local bocce teams over the decades. Again, if you want to travel for cibo delizioso, go to Italy!

The next day, we had a three-hour boat ride on Lake Como. Our skipper and guide made certain to point out and give some history on the villages dotting the coastline and the famous villas.

The following day we traveled north to Domaso for an afternoon at a family-run vineyard and restaurant with views of Lake Como and the Alps! Bellissimo! A family member gave us a wonderful tour of the history and the winemaking facility, as well as the many wines we sampled. We were treated to local charcuterie and ravioli that was made fresh while we were busy sampling. When we received the wine we ordered and shipped back home, they threw in extra gifts for us, with wishes for a Merry Christmas and Happy New Year!

Then we were off to Milan for a chance to try our luck at making our own pasta, sauces, and gelato at a cooking school. Our chef instructor guided us as we made tagliatelle with a pesto sauce and pumpkin ravioli with a cream sauce. Of course, there were wine pairings! He made certain our creations were delicious!

That evening, we donned our fancy apparel and headed to La Scala to take in the opera, "Così fan tutte." The modern take on the comedy was refreshing and the venue was a must-see!

The next day, we were met by our guide, who shared the history of the UNESCO site of Santa Maria delle Grazie and Leonardo da Vinci’s "Last Supper" with expertise and reverence, while keeping us engaged. She likewise inspired us as we toured the Duomo di Milano, San Maurizio al Monastero Maggiore, and the controversial Il Dito sculpture outside the city’s stock exchange.

That evening, we experienced a delightful meal at a Michelin-starred restaurant. The chef, from Naples, created and explained a never-to-be-forgotten bite-sized sampling plate highlighting the tastes of Naples on a plate shaped like the region, with its various borders.

Before leaving Milan, we had a tour of La Scala and its adjacent museum with our guide. She provided us with a history lesson that was quite interesting. That night, we dined at a local seafood restaurant, another treasure clearly favored by the locals. Our waiter was a gem and sent us off with the gift of a bottle of wine.

Our final stop was Turin. Once again, we divided—two of us visited the National Museum of Cinema and the panoramic lift housed in the museum. At the top, we gained a wonderful sense of the city,and the cinema museum was a fun surprise! Our other two toured the Juventus Museum and Stadium, and they thoroughly enjoyed their experience as well.

Our final day, we met our guide, who spent the entire day with us, with only a short break, beginning with a gourmet food tour of traditional Piedmont dishes. Along the way, she shared insights into the history and cultural significance of the foods. Later in the day, she guided us through the Royal Palace of Turin, including the Holy Shroud Chapel, Armory, and Museum. Once again, we were treated to a knowledgeable and entertaining guide.

We departed the next day, leaving with priceless memories of our Italy adventure.

Thank you so much to Zicasso’s travel agent. You helped make our trip come true with such care. Grazie mille!

Overall, this may be too much, but we were happy to have written it down as it allowed us to relive the experience. This was a wonderful trip and we absolutely recommend Zicasso and our travel agent. We are already thinking about our next adventure in Italy. Here are the details...

Planning: Zicasso’s travel agent did a wonderful job of helping us plan a trip, making adjustments and ensuring the adventure turned out perfectly. We interviewed several approaches to planning the trip and our choice with Zicasso’s tour company was the right one for us. The trip app was great and kept everything right at our fingertips. We will definitely reach out to this travel agent when we return to Italy.

Food: How is it that when we stopped on the highway to Florence for a coffee, the food was as good as any high-end restaurant in the United States—organic, fresh, and tasty. One of our crew is gluten sensitive in the United States… in Italy, it’s not the gluten, it’s the chemicals used in the United States. We ate bread at every meal and had no problems. We learned that more simple fare is better fare and just amazing. No need for exotic tasting of cheese, bread, wine, pasta, salad, olive oil, vinegar, with fresh vegetables in the sauce, is all one ever needs… until the gelato at least twice a day.

Logistics: The logistics were great and absolutely essential for first-time travelers. There were guides and drivers to meet us at every stop. They seemed to know what we looked like and were just so very helpful.

Guides: Great choices across the board! Their knowledge and love of their various cities was detailed and charming. It was clear that each city fancies itself as the origin of culture and much more. We loved the perspectives and personalities of the people, and of our guides in Rome, Florence, the Tuscan farm, Venice, the Venice water tour, and Pompeii.

Drivers: Our three drivers, especially the one who got stuck with us on the way to Florence due to an auto accident. He really had an extended day and we really appreciated his patience. We got to know him a little and he was delightful.

Travel by train: It was so easy, fast, and comfortable. We loved the time together and the scenery. The added benefit of the lounge made a big difference from the busyness of the train station. We loved this, all at 300 km/h!

Hotels: The hotels were exactly as described—centrally located, convenient, and very comfortable.

Rome: The best beds and staff!

Florence: The best location—convenient to shops/cafés and breakfast.

Venice: Great location, with window views of the canals; it was very nice, but a bit dated in decor in the lobby. We would still stay there next trip!

Planning and sites visited: Overall, each of the cities and sites were outstanding. They gave us a great insight into Italy as a country, as well as its culture and people. Everyone we engaged with (including hotel staff, restaurants, and locals) was friendly, helpful, and engaging. The pervasiveness of English speakers was incredible. Our single-language approach is something we need to work on in the United States! We always felt safe and well taken care of. The added benefit of this support was that it allowed all of us to focus on the city and countrysides, not the driving. It may cost a bit more, but we felt it was totally worth it.

Roma: Here is the only mistake we made in planning our trip. Doing the Vatican and ruins/Colosseum in the same day is too much. This was clearly our decision and our travel agent suggested that it was “a lot.” Having said that, the pre-purchase and guide is clearly the way to go in whatever city you visit. The three sites are incredible.

Pompeii: We thought this would be neat to see, but not as amazing as the other sites…we were wrong. Pompeii is an incredible site and the pace of the tour was just about right for us. This is a place where you can walk the streets where people have walked since long before Christ. The opulence of their living (steam baths, frescos, statues, and mosaics) is incredible.

Tuscan countryside: The organic farm and cheese-making visit, including a quick trip to Pienza, was an absolute highlight. The lunch was fantastic and inspired us to eat organic! We also loved that to get to the farm you had to travel on gravel roads (well maintained, by the way) and got to see working farms.

Pienza is a beautiful, small village where we could spend an entire day exploring. Next visit, we will carve out a day to shop there and spend the night. There was so much to do in a limited time!!!

Florence: It's just beautiful. The work by Michelangelo just defies explanation and leaves you breathless. The churches are a monument to the wealth and dedication of generations of craftsmen engaged in centuries of work. The cooking class was wonderful and fun, and there was so much food. Making your own tiramisu, pasta, chicken dishes, and sauces was just wonderful.

Venice: We skipped the gondola ride because the tour of the Grand Canal was just incredible. Some of us were a bit spooked by the narrow “streets” or, better yet, passageways. However, we all loved the tour and exploring. One of our crew took off later in the day after the tour and tried to get lost… successfully. But with a bit of iPhone maps and the kindness of the people, they found cafés, open-air markets, an antique shop, children playing football, and a delightful adventure.

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.