12 Day Italy Itineraries & Vacation Packages

Zicasso's travel specialist organized an amazing 12-day series of private tours, taking us from Milan to the lake regions (Como, Maggiore, and Garda) and down to Bologna. Our days were filled with visiting churches, museums (including the Ferrari and Enzo Ferrari museums), a winery, parmigiano, prosciutto, and traditional balsamic manufacturing, a cooking class, boat tours, and food tours.

Along the way, we saw testing at the Ferrari track and a small portion of the women’s Giro d’Italia. With all that, we still had sufficient downtime to search the streets to find our own gems.

Our trip coordinator checked in with us daily to confirm the daily itinerary and transportation. When we had questions or needed to make a change due to the weather, she was thorough, attentive, and responsive in a way that was reassuring and comforting. She was simply amazing.

I would highly recommend using this travel specialist and team for any of your Italian travel needs.

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.

We were so pleased with the travel company. The hotel they suggested was nicely located in Como, with our rooms having a view of the lake and a small balcony. We were also provided a lovely breakfast in the morning.

They suggested a nice, four-day itinerary: a food tour, with the extra bonus of an orientation to the city the evening of our arrival; a wonderful boat ride for four hours on the next day; a trip to Lugano, Switzerland; and then a private transfer, stopping in Bellagio and Varenna on our way back to Milan.

All of the drivers and guides were excellent, although the driver for Lugano thought he was taking us to Bellagio. This may have been due to a switch of drivers due to a schedule change, as the boat ride and Lugano days were switched to make sure we had a beautiful day on the water, as some rain was threatened on the original day.

The travel company also made a lunch reservation in Bellagio for us based on a recommendation we had gotten from our son. The driver for that long day was great about arranging the travel so we could be on time at the restaurant and was there promptly to pick us up when we were done.

We will definitely utilize Zicasso again and would reach out to the travel company if we travel again to Italy.

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.