Rome to Florence Tours & Itineraries

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 had a fantastic time and Zicasso's tour operator did an excellent job organizing every detail of our trip. Drivers and guides were always punctual, and the itinerary was perfectly balanced—full days, without ever feeling rushed.

Some real highlights for us were Herculaneum, the Pantheon, the Vatican, and our unforgettable Capri boat tour. Our guide brought Pompeii's history to life in a way that made it feel like stepping back in time and the Naples street food tour was delicious and nostalgic—her pizza fritta instantly took me back to the calzones I grew up with in Niles, Ohio. Our driver was with us for several days and made every transfer feel effortless.

There was a small hiccup at the very end with a trip planner, but it was minor compared to the overall quality of the trip. The organization, communication, and attention to detail throughout made this a truly memorable experience and we wouldn’t hesitate to book with this tour agency again. We had a fantastic time and the tour company did an excellent job organizing every detail of our trip.

Our trip to Italy was amazing! The tours that were organized for us were all excellent and engaging. 

The Vespa sidecar tour was an incredible way to kickstart the trip and our two teenage boys really enjoyed it. Our walking tours of the Vatican museums and the Colosseum and Roman Forum tours with our guide were excellent. We loved her. She was fantastic. Our tour of the crypts and catacombs was very interesting and the guide was very good.

The hotels were very nice and accommodating, especially in Rome and Venice. The car rental in Rome was good and the car was the perfect size for what we needed. It was just big enough to fit our luggage. 

The hotel in Orvieto was a bit spartan and had plumbing issues. Our tour guide in Orvieto was also great. The hotel in Siena was very nice. Our tour guide in Siena was very nice, but we had some difficulty hearing her. She did explain things nicely and took us to some interesting locations around the city, but not being able to hear her was a little challenging. The e-bike tour in Montepulciano was incredible. The scenic landscapes and the visit to Pienza was a nice surprise. 

Returning the car in Florence was very difficult and our only suggestion is that on the travel documents, the return address be included on the page of the event. We did not think to look back at the rental agreement. Driving in Florence is very difficult and can be overwhelming for some people. 

The train station was organized and it was easy to locate the train. The train ride itself was very easy and fast. 

Venice was outstanding. Our hotel was beautiful and comfortable, and the breakfast was incredible. Due to the difficulty we had in returning the car in Florence, our travel company was kind enough to buy us dinner at an wonderful restaurant in Venice, which was one of the highlights of the trip. 

Our family had a wonderful experience and the trip was so well planned and organized. I will be using our travel company for future trips and, on behalf of my family, I would like to thank you for the time of our lives!

Zicasso set us up with a wonderful travel agent. The process of choosing and communicating through the Zicasso system was easy and helpful.

The travel specialist and her team planned a wonderful 15-day trip, with nine days in Rome and four days in Florence. She found us great accommodations that included a kitchen, which was a must for us. Other travel agents were not able to provide such accommodations.

The drivers we had were professional and picked us up on time. The guides were experts in their field and generally had taught at universities. The guides were very personable and tailored the tours to our interests.

She arranged all the necessary skip-the-line tours. We went to the Vatican with three different tours: the Sistine Chapel, the Gardens, and the necropolis to see St. Peter's tomb.

There were a couple of hiccups in this perfectly planned itinerary. Each time, the travel specialist and her staff were immediately available and guided us through solutions, such as trying to get to the Colosseum during the Roman Marathon.

Zicasso’s travel company and every single guide and driver were stellar. All four hotels were good or excellent. There was one error on the schedule for the day outside of Florence when we had a driver to take us to the Siena region. The schedule stated three hours, so we paid for tickets to the Pitti Palace/garden, which turned out to be wasted money as the driving tour was actually nine hours. It was a beautiful day, though.

Zicasso matched us up with two Italian travel agencies. We provided our dates of travel and approximate travel budget per person. Each agency gave us a preliminary itinerary. We were able to request changes to the itinerary and then chose the one that we preferred. The communication through the Zicasso website was easy and comprehensive.

Our entire trip went off without a single problem. We stayed at a very nice apartment in Rome, 1,000 feet from the Colosseum. We had very knowledgeable private tour guides for the Colosseum and the Vatican, allowing us to skip all of the entrance lines. We had private transfers from the airport to the apartment and from the apartment to the train station. We took a train from Rome to Naples and had another private transfer to a very nice hotel in Ravello. We did a private boat tour of the Amalfi Coast with a captain and a first mate. Drinks and snacks were included. We did a guided hike, which ended at a farm-to-table lunch. We spent a morning in Pompeii, followed by a local wine tasting and lunch.

Every part of the vacation exceeded our expectations. The accommodations were fantastic. The planned activities were just what we were looking for. We still had enough free time to explore on our own and choose which restaurants we wanted to eat at each evening. I feel like we got a great deal for what we paid and would definitely book a vacation through Zicasso again.