12 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.

Our trip to Venice, Florence, Tuscany, Lake Como, and Milan was exceptionally well planned and executed by Zicasso's tour operator.

The transportation from one location to another was efficient, even when challenged by the high tides in Venice. Overall, the hotels selected were very good. The one in Montalcino was exceptional. Every guide was knowledgeable and professional. We appreciated their willingness to be flexible. Our driver for the ride to Como and back to Milan was personable and exceptional as well.

We really enjoyed the truffle hunting experience, the first wine tasting in Montepulciano, where we met the entire charming family, the cooking class in Bellagio with a chef who treated us like family, and the boat rides on Lake Como and to the islands in the lagoon of Venice. All of the dinner reservations were spot-on and when there was a slight misunderstanding regarding our wine tasting in Bellagio, where the staff at the hotel in Bellagio had no idea what had been arranged by our agency, this was quickly resolved by our guide through texts and emails with the agency.

The only aspect of the trip that could have been improved was day eight, when our activities, travel time, and late dinner reservation resulted in a late-night drive back to the villa. The hotel in Milan was difficult to find at first due to its location not being visible from the street. Once we found it and settled in, it was in an excellent location for our sightseeing. The gifts of sparkling wine at two of our stops was thoughtful and appreciated.

We thank our agent and the staff at the agency for a wonderful trip and would not hesitate to recommend the firm to our friends and family.

My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.

Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.

Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.

Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.

What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.

Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.

As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.

Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.

The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.

This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.

This was our first experience with Zicasso’s travel company and, thus, with our travel designer. We were a bit concerned because our trip with a travel company back in 2001 had a few bumps along the road. However, once the private driver arrived and met us after exiting our cruise, all the worries and concerns began to vanish.

Our travel designer created an amazing itinerary and every step of the way was seamless. She took care of every single detail and provided us with all the instructions (guidance, maps, contact information, and all train tickets first class) we needed. All I can say is, she surpassed our expectations. The tours she booked for us showed they were carefully crafted based on our interests and all the guides were magnificent.

She allowed time for us to recover from the train rides; the hotels were perfectly situated, all amazing; and the private transfers were timely and extremely pleasant. She sent drawings of where our drivers would meet us. All I can keep stating is she is amazing!

We boarded the first private transfer at the approved area and our driver drove us to the Bologna train station. When we arrived in Venice, there was a young man waiting for us to take us to our private water taxi, which water taxied us right in front of our hotel. The hotel attendant assisted us with the luggage and checked us in.

She booked us at our hotel in Castello in Venice for three nights. The hotel was on the main street, but was away from the craziness of St. Mark’s Square. We had our first small-group, skip-the-line-tour on day two, with a guide from a local partner who was fantastic. He was witty and knowledgeable. Later we found out he was a professor—no wonder his knowledge of dates and history was so extensive. On our third day we met with a guide, again from the local partner, similar to the day before: small tour, skip the line. Our guide was also fantastic.

After our stay in Venice, we went to Stresa. Again, pick-up from our hotel with the water taxi was timely and the drop-off at the train station was smooth. Once we arrived in Milan train station, there was a driver waiting for us, who took us directly to our hotel. The location was magnificent and we could walk easily along the main street, right in front of the hotel.

The next day we met our guide, who picked us up at our hotel and took us on a full-day excursion to the three islands. He was extremely knowledgeable and worked with us at our pace. His incredible knowledge of history and his kindness won us over. Our travel designer pre-arranged lunch at one of the islands, which was outstanding.

Our last visit was to Como. I was a bit disappointed when we arrived at Como. The main area, where you see the charter boats, seemed small based on my expectations. She arranged a private tour that took us to two islands. That trip showed us the Como I had anticipated. We ended up in Bellagio where we had a late lunch at the restaurant at the tip of Bellagio and the boat picked us up and took us back to the main island. It was beyond words.

If you are visiting Italy, reach out to our travel designer; she will surely exceed your expectations.

First, our travel agent was fantastic and helpful!

Our trip was to visit Lake Como, Venice, Florence, Tuscany, Sorrento, Capri, Amalfi, and wrap up in Rome.

The private cars and drivers were on time and excellent.

The hotels and private bookings, like the boat tour in Como, the coastal ride to Amalfi, and the Vatican in Rome, were just incredible and personal.

I believe we got back every cent we invested in this trip, with Zicasso's help!

We are looking to Zicasso for our 2026 adventure.

It is a must-use resource.

CF