Multi-Generational Italy Vacations & Tours

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!

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.

Overall, the trip was perfect! The hotels were really nice and the itinerary was great.

A few things I would have changed. First, the Amalfi tour day. There was not enough time in Ravello or Positano. We needed more time to relax and shop.

The class of train could have been nicer for the Florence-to-Rome portion of the trip.

We've been to many wineries throughout Europe and the one we went to on our way to Siena was okay, but we have been to much nicer wineries, with better wine and food tastings. It was not a great wine tour experience.

Everything else was wonderful and we really enjoyed the trip with our sons!!!

Thank you!

Italy was fantastic! We visited Venice, Amalfi, Capri, Sorrento, Pompeii, and Rome.

Zicasso’s travel specialist was knowledgeable and patient with me when planning the trip. She was amazing at taking in the information I shared about my family and creating an itinerary that worked well for our family of five (our three children, ages 20, 20, and 22), including food-allergy limitations.

The chosen tours and tour guides were incredible, knowledgeable, engaging, attentive, thoughtful, and a pleasure with which to spend the day or half-day.

When we were in Italy, our travel specialists quickly responded to inquiries and to new requests for transportation needs resulting from unanticipated and good “extra” opportunities.

I highly recommend the travel company and our travel specialists.

My wife and I consulted with a handful of travel agencies in order to pick the right one for us to curate our dream honeymoon, and I could not be happier with our final decision to trust Zicasso’s tour company with this task.

Our travel agent was amazing throughout the process of building our itinerary, choosing experiences that fit exactly what we were looking for in an Italy honeymoon.

Start to finish, our overall experience was seamless. We decided to pack a lot into 10 nights, visiting Tuscany, Venice, Sorrento, and finishing the trip with one night in Rome. The tour company perfectly constructed our itinerary in a way that did not make our experience feel rushed in any of these locations. We had ample time to relax and explore these beautiful places on our own, while also fitting in world-class experiences specific to the region in which we were staying, all hand-selected by the tour company and their local expertise.

Every experience we had was incredible. From a private pasta cooking class and wine tasting in Tuscany to a limoncello tour in a quiet, picturesque village along the Amalfi Coast, each will be an experience my wife and I will never forget.

I would recommend this travel company to anyone visiting Italy for the first time or even those who have been to Italy, but want to experience breathtaking excursions curated by a local team of experts.

Our honeymoon was all we dreamed of and more, and I look forward to having the opportunity to use them for our next adventure.

This was possibly the best trip of my life!

Once I arrived in Venice and put myself in the hands of Zicasso’s tour company, I was supremely well taken care of.

I left my passport on the plane, so I was held up in the airport for probably two hours. This was the first time I used the emergency number (or the chat app). The communication was answered immediately and we were able to let my first guide know I was being held up. I thought the first person who helped me was just someone to get me to the hotel, but she was also a guide in the sense that she described many of the things we saw on the way to the hotel. A very pleasant and gracious guide who made sure also that I was prepared for where to be the next day. It was a very great first experience of the tour company’s service.

Throughout this adventure, the guides were outstanding, the hotels were located practically on top of the interesting sites (especially in Rome) and very pleasant to be in.

Also, I continued to use the emergency number or the chat app multiple times. They were very responsive, very pleasant, and perfectly helpful each time. I don't know if I was high-maintenance compared to other clients the tour company has had, but though I felt like it in my mind, I was treated completely graciously each time.

I loved every destination and I loved having a structured tour, combined with a good portion of free time to explore on my own. Perfect.

I was very well guided on each travel day, being met by drivers to drop me off and to pick me up, and the train travel was very fun.

I think there was only one guide who I thought was just going through the motions, but all the other guides were the height of professionalism. I loved being met by our guides at Doge's Palace, which was absolutely outstanding. Walking around old Florence was great fun! The drive out to San Gimignano and Siena was well-planned and well-guided! In Rome, the guide who took us to the Colosseum and Palatine Hill was outstanding, and it was a great outing. (I had also already pretty much visited all the sights since my hotel was practically in the middle of it all.)

The trip to the Vatican was a whole other story. Unfortunately, I forget that guide's name. This guide was also excellent—entertaining, informative, approachable, and professional. The trip to the Amalfi Coast was a long train ride, followed by a very long car ride, but it was worth it. What a beautiful setting! My trip to Capri was absolutely fulfilling and I was a little sad to say goodbye to the guide—we connected with him so well. The next day was our boat tour from Sorrento to Amalfi and Positano. I absolutely enjoyed being guided by our guides! On the way back after that beautiful excursion, we were just cruising along the water, 1970s music playing, wind rushing by and I had a peak moment of happiness. Truly.

This trip was as if the tour company had read my mind and provided even more than I had imagined. I come away deeply grateful.