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.

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.

We loved everything about our trip to Tuscany. We had great, comfortable hotels as bases to explore the beautiful countryside and towns. Our hotels had kind, welcoming staff. Zicasso's travel company provided helpful suggestions and reserved non-touristy restaurants and enjoyable, interesting activities: eating in Florence, wine tasting in Montalcino, and cheese making in Pienza.

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.

My wife and I consulted with a handful of travel agencies in order to pick the right one for us to curate our dream honeymoon, and I could not be happier with our final decision to trust Zicasso’s tour company with this task.

Our travel agent was amazing throughout the process of building our itinerary, choosing experiences that fit exactly what we were looking for in an Italy honeymoon.

Start to finish, our overall experience was seamless. We decided to pack a lot into 10 nights, visiting Tuscany, Venice, Sorrento, and finishing the trip with one night in Rome. The tour company perfectly constructed our itinerary in a way that did not make our experience feel rushed in any of these locations. We had ample time to relax and explore these beautiful places on our own, while also fitting in world-class experiences specific to the region in which we were staying, all hand-selected by the tour company and their local expertise.

Every experience we had was incredible. From a private pasta cooking class and wine tasting in Tuscany to a limoncello tour in a quiet, picturesque village along the Amalfi Coast, each will be an experience my wife and I will never forget.

I would recommend this travel company to anyone visiting Italy for the first time or even those who have been to Italy, but want to experience breathtaking excursions curated by a local team of experts.

Our honeymoon was all we dreamed of and more, and I look forward to having the opportunity to use them for our next adventure.