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.

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.

The travel assistance from Zicasso's company was very helpful. All tour guides were wonderful, as well as the tours, with the exception of the all-day tour into Tuscany, ending in Siena.

As an elderly woman, I found it to be too long. Also, after the lovely lunch and wine tasting, it was difficult to go on a 3.5-hour walking tour, as well as walk a mile into Siena and a mile out of Siena. Also, the bus did not have great air conditioning and did not have a working bathroom.

The other issue I had was with the seven and nine flights of stairs in Venice and Florence in our hotels. With bad hips and knees, I was confined to going up and down the flights only once during the day. I suggest this be a question for guests in the future.

The travel company was very generous in paying for a wonderful dinner for me and my grandson due to my struggles.

Overall, it was a very good trip. Zicasso’s trip planner was very responsive. In retrospect, I would have spent three days in Tuscany instead of six to see another area.

We enjoyed all of the planned tours in Italy and Greece. Favorites included the Vatican, Colosseum, Roman walking food tour, and a day exploring the Tuscany wine region.

We loved all of our hotels (favorites being our hotel on Via Emilia in Rome and then our hotel on Nikodimou Street in Athens). All of our drivers at our various locales were always on time, even early, and were friendly and engaging.

We did have various questions come up and any time of day/night, Zicasso's travel professional and the tour company were responsive and so helpful.

Our long-awaited 45th anniversary trip came off seamlessly. I appreciate all of the time and planning that went into planning our venture. I will happily recommend you to our friends and family.

Kudos to Zicasso’s tour operator! This is our second time using them, and they didn’t disappoint us. They had to deal with two families, seven in all, all adults, with two separate trips. One trip for all seven to Rome and Florence. Two for Naples and Ischia.

The apartment in Rome was in a good location for us, as we usually stay near there. The only problem I found in this apartment was the smaller unit had a step down into the living room. The floors are dark, and the step needs to be highlighted so one remembers to step down. Several of us kept missing it, and luckily no one fell. Other than that, it was a nice apartment.

In Florence, our apartment was perfect. My husband and I would stay there again; however, it has four bedrooms, four baths, a nice kitchen, and a large living room, so it would be a little big for two people. It was perfect for families. It is on the third floor.

Since my husband and I have been to Rome and Florence many times, we did not have too many requests for tours. My cousin and her family were first-time visitors. I suggested a tour of the Vatican Museums, Ancient Rome, the Accademia Gallery, the Duomo Skywalk, a private tour of the Uffizi Gallery, the Vasari Corridor, and the Boboli Gardens. In Rome, all seven of us did a golf cart ride at night, which seemed to be a big hit. We also had a wine tasting and olive oil sampling in Chianti, which was very nice.

At one point, we thought we were going to have a wedding proposal. A place was planned for the proposal at one of the wineries. Unfortunately, the groom-to-be decided not to do it there since the future bride’s parents would not be there. I felt bad with all the work the travel company did to make this day special for the couple.

Since we were two families, all adults, sharing vacation rentals, the tour operator found two apartments to meet our needs. All of our drivers and guides were on time and very knowledgeable.

We made some last-minute changes on our trip from Florence to Ischia. Changes to the train tickets were made, but we were asked to check with the ferry service to see if they could take us earlier. Our driver went with us to the ticket office and was able to exchange our ferry tickets. Then we notified our travel agent, so they could call the hotel to send our driver earlier than planned.

We have used this tour operator before and would highly recommend them. The hotels they selected were excellent. We stayed at our hotel in Naples last year and asked for the same hotel again. The views were fantastic from our room, and the rooftop bar had views of Mount Vesuvius and the Bay of Naples. The staff were superb, and there was a wonderful breakfast.

We also asked for the same hotel in Ischia, but that hotel closed earlier this year. Another property was selected, our resort in Ischia. Unfortunately, we did not get a chance to use the spa this time, but the hotel had beautiful views from the restaurant, terrace, and our room. Both hotels were beautiful, and the staff were very attentive. Our resort in Ischia was not far from Ischia Porto. A bus stop was a short walk away, and the return stop was right in front of the hotel. The food and drinks were great, and we even walked into town one night, which took about 15 minutes.

I can’t wait to use the travel company again next year.