Italy Christmas Vacations & Tours

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.

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 agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.

Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.

Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.

Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.

Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.

We travel a bunch and I would highly recommend using Zicasso's travel partner.

Overall, this may be too much, but we were happy to have written it down as it allowed us to relive the experience. This was a wonderful trip and we absolutely recommend Zicasso and our travel agent. We are already thinking about our next adventure in Italy. Here are the details...

Planning: Zicasso’s travel agent did a wonderful job of helping us plan a trip, making adjustments and ensuring the adventure turned out perfectly. We interviewed several approaches to planning the trip and our choice with Zicasso’s tour company was the right one for us. The trip app was great and kept everything right at our fingertips. We will definitely reach out to this travel agent when we return to Italy.

Food: How is it that when we stopped on the highway to Florence for a coffee, the food was as good as any high-end restaurant in the United States—organic, fresh, and tasty. One of our crew is gluten sensitive in the United States… in Italy, it’s not the gluten, it’s the chemicals used in the United States. We ate bread at every meal and had no problems. We learned that more simple fare is better fare and just amazing. No need for exotic tasting of cheese, bread, wine, pasta, salad, olive oil, vinegar, with fresh vegetables in the sauce, is all one ever needs… until the gelato at least twice a day.

Logistics: The logistics were great and absolutely essential for first-time travelers. There were guides and drivers to meet us at every stop. They seemed to know what we looked like and were just so very helpful.

Guides: Great choices across the board! Their knowledge and love of their various cities was detailed and charming. It was clear that each city fancies itself as the origin of culture and much more. We loved the perspectives and personalities of the people, and of our guides in Rome, Florence, the Tuscan farm, Venice, the Venice water tour, and Pompeii.

Drivers: Our three drivers, especially the one who got stuck with us on the way to Florence due to an auto accident. He really had an extended day and we really appreciated his patience. We got to know him a little and he was delightful.

Travel by train: It was so easy, fast, and comfortable. We loved the time together and the scenery. The added benefit of the lounge made a big difference from the busyness of the train station. We loved this, all at 300 km/h!

Hotels: The hotels were exactly as described—centrally located, convenient, and very comfortable.

Rome: The best beds and staff!

Florence: The best location—convenient to shops/cafés and breakfast.

Venice: Great location, with window views of the canals; it was very nice, but a bit dated in decor in the lobby. We would still stay there next trip!

Planning and sites visited: Overall, each of the cities and sites were outstanding. They gave us a great insight into Italy as a country, as well as its culture and people. Everyone we engaged with (including hotel staff, restaurants, and locals) was friendly, helpful, and engaging. The pervasiveness of English speakers was incredible. Our single-language approach is something we need to work on in the United States! We always felt safe and well taken care of. The added benefit of this support was that it allowed all of us to focus on the city and countrysides, not the driving. It may cost a bit more, but we felt it was totally worth it.

Roma: Here is the only mistake we made in planning our trip. Doing the Vatican and ruins/Colosseum in the same day is too much. This was clearly our decision and our travel agent suggested that it was “a lot.” Having said that, the pre-purchase and guide is clearly the way to go in whatever city you visit. The three sites are incredible.

Pompeii: We thought this would be neat to see, but not as amazing as the other sites…we were wrong. Pompeii is an incredible site and the pace of the tour was just about right for us. This is a place where you can walk the streets where people have walked since long before Christ. The opulence of their living (steam baths, frescos, statues, and mosaics) is incredible.

Tuscan countryside: The organic farm and cheese-making visit, including a quick trip to Pienza, was an absolute highlight. The lunch was fantastic and inspired us to eat organic! We also loved that to get to the farm you had to travel on gravel roads (well maintained, by the way) and got to see working farms.

Pienza is a beautiful, small village where we could spend an entire day exploring. Next visit, we will carve out a day to shop there and spend the night. There was so much to do in a limited time!!!

Florence: It's just beautiful. The work by Michelangelo just defies explanation and leaves you breathless. The churches are a monument to the wealth and dedication of generations of craftsmen engaged in centuries of work. The cooking class was wonderful and fun, and there was so much food. Making your own tiramisu, pasta, chicken dishes, and sauces was just wonderful.

Venice: We skipped the gondola ride because the tour of the Grand Canal was just incredible. Some of us were a bit spooked by the narrow “streets” or, better yet, passageways. However, we all loved the tour and exploring. One of our crew took off later in the day after the tour and tried to get lost… successfully. But with a bit of iPhone maps and the kindness of the people, they found cafés, open-air markets, an antique shop, children playing football, and a delightful adventure.

Our recent trip to Rome, Florence, and Venice, planned by Zicasso’s travel specialist and her team, was nothing short of exceptional. Every detail was handled with care, precision, and an obvious commitment to excellence. The hotels were truly top rate, perfectly located, and impeccably chosen to enhance the experience of each city. The tour guides were extremely knowledgeable, engaging, and clearly passionate, adding depth and context that made each destination come alive.

What truly set this trip apart was the level of service. From seamless transfers to on-the-ground assistance, everything felt effortless. The recommendations and tips provided along the way were incredibly useful and allowed us to experience each city with confidence and ease. The assistants who helped guide us through logistics and navigation were attentive, professional, and reassuring, making the entire journey feel like true white-glove service from start to finish.

The travel specialist and her team exceeded every expectation. Their planning, responsiveness, and attention to detail transformed an already incredible itinerary into an unforgettable experience. I would recommend them without hesitation to anyone looking for a flawlessly executed, high-end travel experience.

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.