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 1325 reviews
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.
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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.
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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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Zicasso's tour company did a wonderful job of planning our dream honeymoon! Our travel agent took into consideration our wants and wishes, and created half- and full-day activities for us throughout the trip. We were able to visit four locations (Rome, Sorrento, Florence, and Venice) while in Italy. The trip was a perfect mix of relaxation and exploration. The tour company took away the stress of traveling and allowed us to enjoy the days without worries.
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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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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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