Multi-Generational Italy Vacations & Tours

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.

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.

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.

Our Zicasso travel specialist did a fantastic job planning our family vacation for five adults.

Each hotel was top-notch. At the villa in Taormina, the rooms were luxurious, with unbelievable views of the bay and Mount Etna from private verandas. The staff were gracious and the restaurant's breakfast buffet delicious. Lunch and dinner were top-notch. The hotel in Agrigento was modern and the grounds were exceptional. It was close to the Valley of the Temples, with amazing views of the ruins from each room and the beautiful infinity pool. The hotel in Palermo was old-fashioned luxury with up-to-date facilities and close to the old town.

Our tour guides and drivers were excellent.

My only regret is that we only had 10 days to explore Sicily as there was so much more to see!

Our agent did a yeoman's job helping us plan this trip.