Italian Vacation of a Lifetime: Venice, Milan, Florence, Rome

What to expect on this itinerary
This Italian vacation of a lifetime will take you on a 12-day journey through the most famous Italian cities as you will be wined and dined, and ultimately swept off your feet, immersing yourself in the wonders of Roman history and the romance of Venetian canals. Discover the iconic fashions of Milan and the graceful artistry of Florence. You set the pace and revel in the beauty of Italian splendor.
Customizable Itinerary
Venice – City on the Lagoon
You have just arrived in Venice, and already the city enchants you, filled with marbled piazzas and stunning palaces, remarkable history, and elegant décor. Your accommodations are located in the heart of the City of Bridges, where the Rialto Bridge arches over the waterway, showcasing its elaborate 16th-century construction alongside rows of exuberant boutiques. Settle in and enjoy the ambiance of the city as your tour begins.
What's Included:
Venice – Luxuries of the Lagoon
Venice – Finding Venice
Milan – In Fashion
Milan – Magnificent Milan
Florence – Remarkable Renaissance
Florence – Segway into the City
Florence – Marvels of Tuscany
Rome – Enjoying the Piazzas
Rome – Eternal Images
Rome – Roman Relaxation
Rome – Tiber in the Distance
Trip Highlights
- Discover the charm and romance of Venice, from St. Mark’s Square to a serene gondola ride along the Grand Canal
- Witness the remarkable size and imagery of Leonardo da Vinci’s Last Supper in Milan
- Stand beneath the Gothic edifice of the Milan Duomo to see the sensational detail of the celebrated architecture
- Traverse the Renaissance streets, architecture, and art of Florence on a Segway tour
- Experience the majesty of seeing Michelangelo’s David up close
- Explore the fabulous medieval towns of the Tuscan countryside, showcasing how past and present quaintness can blend effortlessly
- Revel in the treasured history and elegant masterworks of Rome, from the Sistine Chapel to Roman Forum
Detailed Description
Rome has the Colosseum, and Venice has gondolas. Milan has the Last Supper, and Florence has David. Each Italian city contains an iconic image filled with enchantment and exoticism, beckoning you to experience the majesty of history set in modern luxury on this Italian vacation of a lifetime. Follow in the footsteps of Roman emperors and window shop in a fashion capital. Sip local wine with a terrace view of lush rolling hills and relish a calming gondola ride during sunset. Italy is more than just romance or fashion, history or opulence, but is instead all of the above.
The journey begins with your arrival in Venice, the city of canals, and Carnival. Your private transfer meets you at the airport and escorts you across the waterway to your luxurious accommodation in the heart of the city. You have two full days to discover the joys of Venice, whether on your own or on a private tour. Explore the Doge's Palace and St. Mark's Square, cruise the canals on a gondola, and venture to the island of Murano to see how the famed Murano glass is made.
After Venice, your private transfer takes you to the central train station where you travel to the glamorous city of Milan. The remainder of the day is at your whim, showcasing the elegant Gothic cathedral and the city's chic ambiance. The following day is yours to discover the splendor of Milan, whether seeing da Vinci's Last Supper or heading into the Italian Alps to linger on the shores of a classic noble getaway at Lake Como.
Your private guide takes you to the train station, where you begin to make your way south to Florence. The Renaissance city brims with tremendous architecture filled with priceless artwork. Explore the city on a guided Segway tour through the historic city center. You make your way into the Tuscan hillsides outside of Florence to visit the stunning medieval towns of Siena, San Gimignano, and Chianti. Continue to Pisa to see the world-famous Leaning Tower.
Then, continue south to Rome, where your private transfer meets you at the train station and takes you to your comfortable hotel in the heart of the old city. Rome is yours for two full days, allowing you the time to take in the exquisite Vatican Museum and discover the immensity of the Roman ruins, such as the Colosseum and Roman Forum. You could even take a tour to Pompeii or the island of Capri located in the Bay of Naples. On your final morning in Italy, your private transfer meets you at the hotel and escorts you to Rome Fiumicino International Airport for your flight home.
Starting Price
$5,600 per person (excluding international flights)
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 900 reviews
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.
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The trip was a vacation of a lifetime! From the start to the end, we couldn't have asked for more. Everything was planned so well and the vacation went so smoothly. We didn't have to worry about a thing and could just enjoy the trip. Zicasso's travel company was amazing and we'll recommend them to all our friends!
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This trip was a graduation present for my son. Zicasso's travel agentt and her team planned us a trip of a lifetime! We spent nine days in Italy, from Venice to Florence, then Rome, and everything was flawless. The transportation, the private tours, reservations for meals, and lodging were perfect! Our agent's attention to detail and personalization of the trip was as good as I have ever seen and it exceeded our expectations. I could have never planned a trip like this on my own. I would not hesitate to book another trip using them and have recommended the company to all of my friends.
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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.
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My wife and I recently returned from our first trip to Italy and want to highly recommend Zicasso's travel specialist and her company for creating the perfect vacation for us. It was a two-month process of back and forth, but no matter what we asked of her, she delivered several options.
We had a perfect mix of historical Florence and its museums, and wonderful restaurants, and the Tuscany and Umbria countryside experience. And on our first day, when our flight into Florence got diverted to Milan, we had the peace of mind that our travel specialist was there to help with her much appreciated support.
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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.
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