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 565 reviews
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 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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We just got back from our trip to Venice, Florence, and Rome, with me, my wife, our two teenage boys, and my parents. Zicasso's travel agent made our vacation amazing. He went above and beyond to accommodate our needs and plan our excursions exactly how we hoped, better even. His attention to detail, quick response time, and professionalism are the best I've experienced in the travel industry. I've already recommended his services to a friend who is planning a trip to Italy with their family next year. Thank you for making our time in Italy one we will all remember!
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I am so happy we worked with our Zicasso travel agent for our 11-night visit to Venice, Florence, and Rome. We had a wonderful Italian experience. Our agent was everything you hope for in a travel specialist: knowledgeable, thoughtful, helpful, gracious, and kind.
Upon hearing our initial ideas for the trip, she quickly put together a plan on how best to allot our time. Thereafter ensued exchanges regarding hotels, sightseeing, guides, and transfers. She listened to our thoughts, desires, and questions, making many useful suggestions, including hotel choices. She always prioritized our wants and concerns. She organized the travels quickly, as we contacted her only two months prior to departure.
Once we agreed to the program, she sent us a brochure PDF laying out details for each day of the trip that included hotel confirmations, transfer details, vouchers for museums, a cooking class, a Tuscany day trip with wine, cheese, and olive oil tasting, a gondola ride, Venice lagoon boat excursion, basilica entrance tickets, and guided tours of each city, the Vatican, and Colosseum.
Upon arrival in Venice, our agent met us at the airport and escorted us to our water taxi. She kept in touch with us daily, texting a reminder of the next day’s schedule, along with numbers for guides and drivers if applicable. Everything she planned went smoothly, without a single hitch.
When you begin the process with Zicasso, it feels akin to a shot in the dark. The site provides the names of two companies and you’re left to decide who to work with. I couldn’t be more pleased with the trip our agent designed. Book with her; you will be in the best of hands.
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The Zicasso trip with this travel agency and their team surpassed our expectations.
Their attention to detail during our 16-day vacation to Rome, Florence, and Venice ensured no aspect of the trip was overlooked. From the associate meeting us at the airport on arrival to the assistant sending us off on departure, everything was well organized and proceeded without issues.
The accommodation was exceptional, featuring boutique hotels in the center of our activities that exuded charm and provided unparalleled comfort. The staff at the hotels were very pleasant and helpful.
Transportation was always prompt and comfortable, getting us directly to our planned activity on time. Local guides brought destinations to life with their expertise and enthusiasm. All guides were exceptionally knowledgeable about Italian civilization, history, art, and architecture. Recommendations for various Italian cuisine was exquisite, from providing suggestions to securing reservations.
This trip was more than just a vacation – it was a deeply enriching experience that created lasting memories, celebrated the culture of Italy, and exceeded every expectation.
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From the moment we began working with Zicasso's trip planner, our every need was met. He listened and planned an epic trip based on our conversations. Then, for our trip, we worked with another trip planner who was extremely responsive and professional, especially when we were in Italy. Any questions we had were promptly answered. Everything they planned was pure luxury and fantastic. The private pick-ups, drivers, and tour guides were absolutely prompt and fantastic. Every tour was super-fun and informative. Highlights included the wonderful hotels, food tour in Florence, tour in Venice, cooking class, and tasting track in Tuscany. I would highly highly recommend. It was a five-star, wonderful trip!
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