Italy’s Great Cities Tour: From Rome to Venice

We had a fantastic trip, all thanks to our travel specialist. We spent a few days in Siena, touring different Tuscan towns like Montepulciano, Pienza, and San Gimignano, and then we spent a couple of nights in Florence. All of our drivers and guides were very thoughtful that we had my two-year-old nephew with us.

Our first trip to Italy was a romantic anniversary celebration, and thanks to Zicasso’s travel specialist and our travel company, it became one of the most extraordinary and meaningful travel experiences of our lives. It was everything we had dreamed of, and so much more!

From our very first conversations, she took the time to understand who we are as travelers: our love of art, architecture, history, culture, food, wine, and lifelong learning. She translated those passions into an imaginative, beautifully personalized journey through Rome, Tuscany, Florence, and Venice.

One of her greatest gifts is her intuitive understanding of the rhythm of travel. We wanted days filled with discovery, learning, and new experiences, but also leisurely afternoons and evenings to wander cobblestone streets, linger over wonderful meals, and simply absorb the atmosphere of Italian life. She struck that balance perfectly. Our itinerary was wonderfully rich, yet never rushed or overscheduled.

The private guides she selected were exceptional: not simply knowledgeable, but gifted teachers and storytellers who brought centuries of Italian history, art, architecture, and culture vividly to life. In Florence, for example, our guide helped us explore the Renaissance through fascinating stories of the Medici family, Michelangelo’s creative process, and the philosophy of Humanism. Our visits to the great museums and historic landmarks became intellectually stimulating and deeply engaging experiences.

She also introduced us to Italy’s living traditions: a fabulous food tour in Rome, wine tasting in Tuscany, explorations of enchanting medieval towns and villages, and boat excursions to Murano and Burano, where we discovered the centuries-old artistry of glassblowing and lacemaking. These experiences gave us a wonderful sense of the richness and continuity of Italian culture.

Her choices of accommodations were equally inspired. Each was distinctive, beautifully located, and full of character, from a charming, peaceful boutique hotel near the Pantheon in Rome, to a magical stay in a medieval Tuscan village, an elegant Art Deco hotel in Florence, and a fairytale suite in Venice. Every setting added another layer of romance and delight to our anniversary celebration. And the cuisine was heavenly! Every meal was memorable, culminating in a dreamy farewell dinner beside a Venetian canal.

Behind all this magic was the travel specialist’s impeccable planning, extraordinary attention to detail, and genuinely proactive care. Every transition, from airports and private transfers to trains and boats, was seamlessly coordinated.

One small example perfectly captures her approach. When our train from Florence to Venice was delayed, we contacted the travel specialist to let her know. She immediately reassured us that she was already monitoring our train and had informed our guide in Venice of the delay. There was nothing for us to do but relax, enjoy the ride, and look forward to the magnificence of Venice! That kind of thoughtful anticipation gave us complete peace of mind throughout our travels.

Equally special was her warmth and genuine personal connection. She was always accessible, and we found ourselves exchanging messages most days, not because anything needed fixing, but simply because it was such a pleasure sharing our experiences with her. She combines exceptional professionalism, creativity, and meticulous organization with kindness, generosity of spirit, and a contagious passion for sharing the beauty of her country. By the end of our journey, we felt we had gained not only an extraordinary travel advisor, but also a wonderful new friend.

Italy opened our minds, elevated our souls, and deeply touched our hearts. Our travel specialist didn’t simply organize a magnificent vacation; she opened the door to a country and culture we have now fallen completely in love with.

We cannot recommend our travel specialist and travel company highly enough. For anyone seeking a thoughtfully curated, culturally immersive, deeply personal, and truly unforgettable Italian journey, she is an exceptional choice.

We are already dreaming of returning to explore Sicily and Sardinia with our family, and there is absolutely no question who we will call!

Thank you for giving us far more than a beautiful vacation. You gave us an extraordinary gift: memories, discoveries, and connections we will treasure for the rest of our lives.

The cities we visited were wonderful. We really enjoyed the tours, especially the cooking class with our chef! I will be making homemade ravioli over the holidays.

The hotels were located close to the city centers. But the hotel in Bologna was very close to the university, with lots of graffiti and live music late into the night. The hotel, however, was quaint and very nice. The hotel staff was very friendly and accommodating.

The hotel in Florence was just weird. Our travel companions' room had no windows and was small. Ours was oddly laid out but much bigger. The desk person told us both rooms were the same when we first checked in. If we came back after 9 p.m., there was no hotel staff, and we had to use a code to walk through an apartment lobby.

The hotel in Venice was situated right in the middle of lots of restaurants and gelato! The hotel was by far the best one, with much nicer amenities and rooms. It had a bar and restaurant on-site. It was a good way to end our trip.

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 an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.

The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.

The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.

One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.

Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.

While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!

Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.

Every experience felt personal, meaningful, and special.

This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!

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!