7-Day Food and Wine Tour of Tuscany

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.

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’s travel specialist and her team crafted a wonderful 10-day trip to Tuscany, Cinque Terre, and Florence for my husband's 60th birthday. All the hotels were beautiful boutique hotels that we probably would not have found if we were planning it ourselves. The same was true with the experiences they booked for us. They have the local connections and can provide experiences you may not easily find by searching the internet.

We loved that our wine tastings were at smaller local wineries. All our guides were very friendly and very knowledgeable. All our drivers were always on time. They took care of reserving our train tickets, as well as dinner reservations. We felt very well taken care of throughout the entire trip.

This travel company was incredibly difficult to work with, and I would not recommend them. The travel agent seemed very annoyed when we asked basic questions about our itinerary. For example, the itinerary he sent us did not have the correct number of rooms booked for our party. When I asked him about it, he rudely told me, "Of course I have booked the right rooms". Later, we found out he was working off the wrong itinerary - our final invoice was based on this wrong itinerary and had a much higher amount than we actually owed. When we pointed that out, he went from being annoyed to flat out rude.

We also identified many gaps in transportation and logistics, with the travel agent continuing to be rude when we asked for clarification or support in fixing the gaps. For example, he had us driving a rental car to the Bologna airport at around 3 AM from rural Italy to make an 8 AM flight. We would be driving right through Florence on the way to Bologna. When I asked why we didn't simply take a later flight out of Florence, I was told there were no options to do this. A simple Google search identified several flights out of Florence at a more reasonable time.

We finally had Zicasso step in, and they were incredibly helpful in cleaning up our itinerary. Unfortunately, we still experienced several logistical issues during our trip despite Zicasso's support. For example, we were dropped off by drivers at train stations and were then on our own to figure out how to get to our hotels - all required lengthy walks up hills to access, and my 81-year old father was not able to do that. So we had to find our own transportation or have my dad attempt to walk (not good at all). As another example, my father really wanted to see the Matterhorn. The travel agent said it was an easy "day trip" from our hotel to the Matterhorn. It turned out to be a 3.5 hour drive each way. The driver left us at a train station below Zermatt (town below the mountain) to figure out on our own how to navigate the city of Zermatt. We had no guidance from the travel agency on how to best see the Matterhorn, and Zermatt was another town with steep hills that my dad had to walk through (with a cane) as we tried to figure out how to best see the mountain. Due to the length of the drive to Zermatt from our hotel, we had less than two hours in Zermatt because the travel company had booked us on a 6:15 AM train the next morning to leave Switzerland. It was a wasted day instead of being the wonderful experience my father had hoped for.

The best part of the trip was the hotels, and the travel company gets credit for selecting hotels with wonderful views and great breakfast options. They were not easily accessible from the local towns, so we had to figure out taxis and shuttles to get to nearby sites.

Most of the time, we were left on our own to find our way around. But we did have a guided tour in Florence and a knowledgeable driver that took us to a winery in Tuscany. Both of these guides were amazing, and it would have been nice to have more guided support throughout this trip (especially in Zermatt).

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!

We had a fantastic experience for a first-time trip to Italy. I wasn't sure how this would be, considering I learned about Zicasso while trying to plan the trip myself. Zicasso put me in touch with a travel specialist and the whole team was incredibly responsive to my many, many questions. If they were ever annoyed, it didn’t show.

I really wanted a smooth experience for my family of five, including three teens, one of whom has Celiac. Our agent was great in helping plan out the experience we wanted. As you may know, it is challenging to find rooms for five in Europe, but the travel company found apartments (usually two bedrooms with a pull-out couch) in the heart of town. You can really customize what you do, but we elected to plan our own meals and handle some of our own transport. We did have one issue where the van driver taking us to the train failed to show. I got one with Uber and the travel company quickly (I mean before we got home quickly!) refunded that amount.

Our contact in Italy was amazing and patient. I can’t give her enough credit. Any time I was unsure of something, she was there. The tours were great, especially Florence and Rome. You may be able to find the companies online, but ours seems to have the connections to get the best guides.

As for meals, we didn’t have any issues. We used an app and got a few recommendations from the travel company and local guides. Even our wine-tasting tour out in Tuscany was accommodating.

I would use our travel company and Zicasso again. I think the only downside is we tried to cram a lot in and it was hot. I probably should have asked for one to two fewer or shorter walking tours, especially on days we switched cities. Otherwise, it was excellent.