Florence and Venice Itineraries & Tours

We had a fantastic trip, all thanks to our travel specialist. We spent a few days in Siena, touring different Tuscan towns like Montepulciano, Pienza, and San Gimignano, and then we spent a couple of nights in Florence. All of our drivers and guides were very thoughtful that we had my two-year-old nephew with us.

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.

The cities we visited were wonderful. We really enjoyed the tours, especially the cooking class with our chef! I will be making homemade ravioli over the holidays.

The hotels were located close to the city centers. But the hotel in Bologna was very close to the university, with lots of graffiti and live music late into the night. The hotel, however, was quaint and very nice. The hotel staff was very friendly and accommodating.

The hotel in Florence was just weird. Our travel companions' room had no windows and was small. Ours was oddly laid out but much bigger. The desk person told us both rooms were the same when we first checked in. If we came back after 9 p.m., there was no hotel staff, and we had to use a code to walk through an apartment lobby.

The hotel in Venice was situated right in the middle of lots of restaurants and gelato! The hotel was by far the best one, with much nicer amenities and rooms. It had a bar and restaurant on-site. It was a good way to end our trip.

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!

Edwin and I struggled during this trip. It started in Venice with the hotel room and location. Horrible room with little or no amenities. Please note, the other hotels were much better.

There should have been better communication between Zicasso’s travel company and us. I was unaware we were not going to have local tour guides in Arezzo, Montepulciano, Verona, Orvieto, Cortona, etc. The drivers took us to these locations and dropped us off in the piazza or city gates and we were on our own. The drivers shared some notes about the city, but we wandered aimlessly most of the time. Please note, the local guides in Venice, Florence and Rome were great.

As per the restaurants, I had received recommendations from friends and family, which I shared with the travel company. They made the reservations on our behalf. However, they never told us how far the hotels were from these restaurants. It would have been nice for them to tell us. As a result of the distance, we asked the travel company to cancel some of the reservations on our behalf.

The three positive things I can say are as follows:

The travel company responded quickly when we called them from Italy.

The private drivers in Venice (from airport to hotel), Verona (driver), Florence (driver) and Rome (hotel to airport) were great. However, the driver from Florence to Rome with a stop in Orvieto was terrible.

The local tour guides in Venice, Florence and Rome were great.

All in all, we were not happy and very disappointed with this trip.

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!