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

The Cathedral of Santa Maria del Fiore in Florence at sunset.

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.

Countries Visited

Italy

Places Visited

Venice, Milan, Florence, Rome

Suggested Duration

12 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Day 2

Venice – Luxuries of the Lagoon

Day 3

Venice – Finding Venice

Day 4

Milan – In Fashion

Day 5

Milan – Magnificent Milan

Day 6

Florence – Remarkable Renaissance

Day 7

Florence – Segway into the City

Day 8

Florence – Marvels of Tuscany

Day 9

Rome – Enjoying the Piazzas

Day 10

Rome – Eternal Images

Day 11

Rome – Roman Relaxation

Day 12

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)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

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.

4.9

Verified Traveler Reviews

Based on 827 reviews

Italy Travel Review: Rome, Siena, Florence, Venice, Colosseum, Roman Forum, Vatican City, Sistine Chapel, St. Peter's Basilica, Wine Tasting, Uffizi, Doge's Palace, 16 Days

When we decided to plan a family trip to Italy, I did some research and found Zicasso. They were very highly rated, and we reached out to them. Zicasso’s travel agent responded very quickly. She was friendly, professional, and asked us questions to ensure she knew what we were looking for in our trip. The travel agent planned an exceptional family vacation for us with a customized itinerary that included traveling to Rome, Siena, Florence, and ending in Venice. She tailored our trip to include private transfers from the airport to the hotels, as well as traveling city to city.

Each hotel had an excellent location that allowed us to easily walk and explore. The hotels were beautiful, clean, and comfortable, each with impeccable service.

They set us up with private tour guides, who not only allowed us to skip the lines to major attractions, but also personalized the tour so we were able to spend time viewing the things that were important to us. The guides were friendly, informative and engaging.

Every aspect was meticulously curated and the travel company checked in with me via a messaging app daily to share the next day’s itinerary. They were always available if we had any questions or if any issue arose, which never did because of how well they planned everything. I reached out to them asking if they could please make a dinner reservation for me and they were quick to secure that for us.

I would highly recommend this travel company and will definitely use them again in the future.

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Italy Vacation Review: Venice, Florence, Rome, Accademia, Private Tours, 9 Nights

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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Italy Trip Review: Rome, Florence, Tuscany, Vatican, Colosseum, Cooking Class, Food Tour, Cheese Sampling, Wine Tasting, 10 Nights

We've taken many family vacations over the years, but we all agreed this was the best one yet!

The team at Zicasso’s travel company did an exceptional job tailoring the perfect trip for our family. Every detail was thoughtfully planned, making the entire experience seamless and truly enjoyable from start to finish.

We had wonderful drives and knowledgeable, engaging tour guides who made each destination come to life. Some of our favorite highlights include a hands-on cooking class in Florence, exploring the beautiful Tuscan countryside, and having effortless access to iconic sites like the Vatican and the Colosseum.

The experiences were unforgettable, from the best food tour in Rome to a fun and unique golf-cart tour through the city. We also loved visiting a Parmigiano-Reggiano factory and a Parma ham producer, along with an extra-special stop at the Ferrari Museum that was such a memorable surprise.

Every moment felt thoughtfully curated and we came home with incredible memories that we will cherish for years to come. We highly recommend the travel company to anyone looking for a truly personalized and exceptional travel experience.

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Italy Family Vacation Review: Venice, Verona, Florence, Tuscany, Siena, Rome, Biking, Cooking, Wine Tasting, Olive Oil Experience, 10 Nights

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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Italy Trip Review: Venice, Florence, Rome, Burano, Tuscany, Trastevere, Jewish Ghetto, Vineyard Visit, Local Cuisine, 9 Days

We chose Zicasso’s travel company to organize a nine-day trip to Venice, Florence, and Rome for our family of four adults. My wife and I are in our 50s and our two sons are in their early 20s. We all love to travel, but have a range of interests when it comes to experiences, activities, and cuisine. The travel company created an itinerary that gave each of us something memorable.

Everything was planned and executed with care. Hotels were thoughtfully selected, transportation kept us moving without feeling rushed, and every tour guide was exceptional. The team also checked in periodically to make sure we were having the best experience possible. We've traveled internationally many times and this ranks among the very best.

Nine days is just a taste of what Italy has to offer, but our "sampler" tour left all of us excited to return and explore more.

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Italy Tour Review: Venice, Florence, Rome, Naples, Pompeii, Tuscany, St. Mark's, Food Tour, Vineyard Visit, 2-Week Trip

The travel professionals at Zicasso’s travel company worked with us for over a year to plan the most amazing 14-day tour of Venice, Florence, and Rome. They were beyond patient and kind, fielding my endless questions and providing assurances for every detail. Every day was jam-packed with guides and travel. Well, one really doesn't know until you get to Italy, right?

Upon our late-evening arrival to Venice, we had our personal escort waiting for us at the airport, with private transport to our hotel in Venice. She did not leave until we had our bags in the lobby. I knew right then and there we had made the right choice with the travel company.

We found that everything was taken care of by the travel company, down to the smallest detail. Every guide, and there were many, came to our hotels to greet us and escorted us back to our hotel upon conclusion of our tour. Every single guide was a treasure. We never had to hail a taxi, which to me was the most amazing thing, as the travel company had private drivers picking us up or waiting for us at hotels and train stations.

Upon leaving Venice for Florence, our personal escort from the airport was waiting for us at the hotel, with a water taxi to the train station. She walked us through the train station and showed us how to find our gate for our train to Florence. Upon arrival in Florence, we had a private driver waiting for us for transport to the hotel. Same from Florence to Rome, Rome to Naples (for Pompeii and back to Rome).

We had multiple food tours and they were all amazing. We spent every day with private guides. Believe me, the travel company knows the very best guides in Italy. They are there 24/7 for you if things don't go as planned. Trust me on this.

In Venice, our tickets for St. Mark's Basilica that were reserved for our guide disappeared. There we were, no access. Our guide tried to secure tickets on her own and access was sold out. She called the travel company, which somehow secured access, even to the second level, where we could visit the four bronze horses.

Did I mention our day in Tuscany? The travel company insisted we were spending too much time with tours and insisted we take a day in Tuscany. We visited a vineyard in Tuscany for what turned out to be a private tour and lunch hosted by the vineyard owner. We had a table set up overlooking the vineyard and indulged in what may have been the best food we experienced in all of Italy. Everything was made on-site and perfectly paired with the vineyard wines. We were entertained by her three wonderful dogs, two of which were lovable and goofy Labrador retrievers. What a perfect day!

Without a doubt, the travel company is the finest travel agency we have ever had the privilege to work with. As I said earlier, everything was taken care of, nothing was missed: drivers, trains (business class), guides, food tours. The best vacation we have ever had.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

31,000+ Verified Traveler Reviews