10 Day Italy Itineraries & Vacation Packages

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 the pleasure of working with Zicasso’s travel agents to create the perfect Italian adventure. I had quite a few specific requests, from travel logistics to hotel preferences, and they were incredibly patient and collaborative, offering multiple variations of the itinerary until it matched exactly what we envisioned.

Our journey began in Venice, where we were seamlessly picked up by a private driver, transferred to a water taxi, and dropped directly at our hotel. After a wonderful stay, we were taken by private driver to the train station for our ride from Venice to Florence, our one and only train trip, as we opted (based on their smart recommendation) for private transportation for the rest of our travels to avoid potential delays and enjoy added convenience.

From Florence, we were driven into the Tuscan hills, where we experienced magical wine tastings, vineyard tours, olive oil tastings, and unforgettable meals with wine pairings. 

Next, our private driver brought us to Pompeii, where we enjoyed a fascinating tour with our private guide, and then continued on to Rome. In Rome, we loved the private golf cart tour of the city’s major landmarks, as well as a delightful cooking class that was arranged for us; it was a real highlight!

Finally, we traveled by private driver to Sorrento. From there, we had a breathtaking driving tour of the Amalfi Coast, a lemon farm tour, and an amazing day trip to Capri. Every detail was thoughtfully planned and executed.

Summary:

Planning and Itinerary Creation: Zicasso’s consultants made the entire process easy and stress-free. They worked closely with us to perfect the itinerary and were always receptive to changes and feedback.

Hotels: My sister and I requested adjoining rooms and were provided with beautiful family suites throughout the trip. Each hotel was ideally located, comfortable, and well-appointed, with all the amenities we needed.

Transportation: Every transfer was smooth and punctual. The private drivers were professional, friendly, and knowledgeable. (A special shoutout to our driver in Florence/Tuscany – he was the best!)

Communication: Throughout our trip, the travel company’s team was always accessible. Whether we needed to make adjustments or had a question, they handled everything promptly, allowing us to relax and fully enjoy our vacation.

We spent just over two unforgettable weeks in Italy and it was absolutely perfect, all thanks to the hard work, attention to detail, and excellent communication from Zicasso’s travel company! I highly recommend them and would not hesitate to use them again for future adventures.

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.

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.

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.