Luxury Italy Tour in 14 Days

What to expect on this itinerary
Classic beauty and indelible charm will radiate from ancient ruins, Renaissance artwork, and captivating coastlines during your custom-tailored 2-week tour of Italy. The iconic wonder of Italy will seduce you with panoramas of the rugged Amalfi Coast and the glamour of St. Mark’s interior shimmering with gilded mosaics. The Colosseum reflects remarkable achievement of ancient engineering and the Uffizi Gallery displays the triumphs of spirited expression. Wander along the cherished shores of Lake Como and travel into the past while strolling down the streets of Pompeii. Embrace Italy as an embodiment of culture with classic style and timeless charisma.
Customizable Itinerary
Milan – Italy’s Fashion Capital
Your flight will land at Malpensa Airport, where your private transfer greets you. Settle into the luxuries of your fantastic accommodations at the heart of the city with the remainder of the day at your leisure to discover the beauty of Milan. The city of Milan embraces its elegance and sophistication that are displayed through the preserved architecture, ravishing artworks, and famous connections to the fashion industry. The fast pace of the city thrives on creativity that celebrates the modern metropolis and the cultural grandeur that dates back to the 5th century BC under Celtic settlers.
What's Included:
Como – Lakeside Como to Visit the Surrounding Towns
Como – Beauty around Lake Maggiore and Borromean Islands
Venice – After-Hours St. Mark’s Basilica Tour
Venice – The Canals of Venice and the Island of Murano
Vernazza – Famous Cinque Terre by way of Lovely Verona
Vernazza – Prominent Trail Connecting the Towns of Cinque Terre
Florence – Remarkable Pisa and Lucca before Arriving in Florence
Florence – Art and History in the Uffizi and Accademia Galleries
Rome – Beauty of Assisi before an Introductory Tour of Rome
Rome – Sensational Art and Unique History of Vatican City
Sorrento – Vast Ancient Pompeii en route to Sorrento
Sorrento – The Natural Splendor of the Amalfi Coast
Sorrento – Depart for Home
Trip Highlights
- Explore the grandeur of St. Mark’s Basilica on an after-hours tour to savor the history, the artwork, and the ambiance without the large crowd
- Embrace the beauty of the Vatican with a private tour shedding light on exceptional masterworks from artists like Raphael and Michelangelo
- Bask in the tranquil charms found around the five towns of Cinque Terre on the Ligurian coast by taking the scenic paths linking to vistas and historical lanes
- Witness the infamous lilt of the Leaning Tower of Pisa, a structure embodying the former rise and fall of the maritime powerhouse
- Delight in the ravishing splendor of the Amalfi Coast with a private driver who will showcase its present and former glory
- Stroll along the extravagant architectural design of the 17th-century villa of Count Vitaliano Borromeo known for its lavish gardens and stunning décor
- View the masterful works quintessential of the Renaissance in Florence, including the unforgettable works like Michelangelo’s David
- Follow in the footsteps of St. Francis to discover the stunning Umbrian scenery and magnificent architecture of the two-story cathedral
- Visit the incredible ancient city of Pompeii, which was preserved in pumice and ash after an infamous eruption of Mount Vesuvius
Detailed Description
Your 14-day Italy tour takes you from north to south emphasizing experience with an immersive exploration of history and heritage. From food to architecture, distinctive cities to mesmerizing natural beauty, Italy encompasses a special place in the annals of the Western World through its support of, and addition to, philosophy, art, and design. From Milan to Naples, Venice to Pisa, Florence to Rome, the famous cities of Italy boast connections of renowned artists capturing the former zeitgeist in preserved palaces and artworks, while smaller towns enchant you with surprising medieval streets, maintained customs, and hidden treasures of their own.
Your discovery of Italy begins with your arrival in Milan. Spending time in Milan allows you to visit the cathedral and the Santa Maria delle Grazie, home to da Vinci’s The Last Supper. The grace and elegance of Northern Italy are visible in both the cities and the towns taking you into the alps to visit Lakes Como and Maggiore, as well as down to the Venetian Lagoon to explore Venice and the glassblowing island of Murano. While exploring the famous waters of Italy’s lakes region, the elegance of small towns in view of mountainous expanses combines luxury with natural majesty.
Venice’s canals will bring more than a quintessential gondola ride leading you to the wonders of St. Mark’s Square, including the eponymous basilica. The island of Murano links the artistry of glassblowing with the history of the Venetian Republic. Traveling west gives you time to stroll through the streets and piazzas of Verona, home to the exciting summer Opera Festival featuring Puccini in 2019 and home to house of Shakespeare’s Juliet. When visiting the five towns of Cinque Terre, the magnetism derives from tower homes and narrow streets, terraced coastal slopes and gorgeous Ligurian Sea.
The celebrated region of Tuscany is located in Central Italy, boasting cities like Pisa, Lucca, and Florence. While in Tuscany, you will visit the Piazza dei Miracoli, home to the renowned Leaning Tower, and also stroll around the stunning preserved Renaissance walls of Lucca. Discover the stunning streets of Florence’s historical city center before witnessing the collections of masterful Renaissance artists inside the Uffizi Galerie and Accademia dell’Arte. The magnificent town of Assisi is located on the slopes of Mount Subasio and features the sensational Basilica of St. Francis.
The city of Rome is known as the Eternal City for its ability to evolve with the ruling classes of society over more than 2,500 years. Touring the city unveils renowned images like the Colosseum, the Trevi Fountain, and the Pantheon. While Vatican City is an independent nation, its proximity inside the greater municipality of Rome makes it a fabulous destination to view the evolution of Christianity across the globe including the influence of the Papal State on the Western World.
Traveling south of Rome brings you to the Bay of Naples and the city of Pompeii. The classic city is known for being buried in the elements after a massive volcanic eruption. The structures retain their artistry and integrity drawing tourists from around the world. The drama of the Amalfi Coast stems from the narrow road that winds alongside the cliffs, and towns like Amalfi, Positano, Ravello, and Minori represent the rise and fall of industrial city-states before the reunification of Italy.
Starting Price
$6,300 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 896 reviews
We had the pleasure of working with Zicasso’s travel agents to create the perfect Italian adventure. I had quite a few specific requests, from travel logistics to hotel preferences, and they were incredibly patient and collaborative, offering multiple variations of the itinerary until it matched exactly what we envisioned.
Our journey began in Venice, where we were seamlessly picked up by a private driver, transferred to a water taxi, and dropped directly at our hotel. After a wonderful stay, we were taken by private driver to the train station for our ride from Venice to Florence, our one and only train trip, as we opted (based on their smart recommendation) for private transportation for the rest of our travels to avoid potential delays and enjoy added convenience.
From Florence, we were driven into the Tuscan hills, where we experienced magical wine tastings, vineyard tours, olive oil tastings, and unforgettable meals with wine pairings.
Next, our private driver brought us to Pompeii, where we enjoyed a fascinating tour with our private guide, and then continued on to Rome. In Rome, we loved the private golf cart tour of the city’s major landmarks, as well as a delightful cooking class that was arranged for us; it was a real highlight!
Finally, we traveled by private driver to Sorrento. From there, we had a breathtaking driving tour of the Amalfi Coast, a lemon farm tour, and an amazing day trip to Capri. Every detail was thoughtfully planned and executed.
Summary:
Planning and Itinerary Creation: Zicasso’s consultants made the entire process easy and stress-free. They worked closely with us to perfect the itinerary and were always receptive to changes and feedback.
Hotels: My sister and I requested adjoining rooms and were provided with beautiful family suites throughout the trip. Each hotel was ideally located, comfortable, and well-appointed, with all the amenities we needed.
Transportation: Every transfer was smooth and punctual. The private drivers were professional, friendly, and knowledgeable. (A special shoutout to our driver in Florence/Tuscany – he was the best!)
Communication: Throughout our trip, the travel company’s team was always accessible. Whether we needed to make adjustments or had a question, they handled everything promptly, allowing us to relax and fully enjoy our vacation.
We spent just over two unforgettable weeks in Italy and it was absolutely perfect, all thanks to the hard work, attention to detail, and excellent communication from Zicasso’s travel company! I highly recommend them and would not hesitate to use them again for future adventures.
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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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We were so pleased with the travel company. The hotel they suggested was nicely located in Como, with our rooms having a view of the lake and a small balcony. We were also provided a lovely breakfast in the morning.
They suggested a nice, four-day itinerary: a food tour, with the extra bonus of an orientation to the city the evening of our arrival; a wonderful boat ride for four hours on the next day; a trip to Lugano, Switzerland; and then a private transfer, stopping in Bellagio and Varenna on our way back to Milan.
All of the drivers and guides were excellent, although the driver for Lugano thought he was taking us to Bellagio. This may have been due to a switch of drivers due to a schedule change, as the boat ride and Lugano days were switched to make sure we had a beautiful day on the water, as some rain was threatened on the original day.
The travel company also made a lunch reservation in Bellagio for us based on a recommendation we had gotten from our son. The driver for that long day was great about arranging the travel so we could be on time at the restaurant and was there promptly to pick us up when we were done.
We will definitely utilize Zicasso again and would reach out to the travel company if we travel again to Italy.
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I can confidently say that Zicasso's travel specialist is truly dedicated to providing her clients a luxury experience. From the outset, we had a 20-minute call where she wanted to learn about our dream vacation and get to know us. She was attentive to every request we made and organized our itinerary accordingly. During the trip, she texted us daily to inform us about our drivers and guides for the next day. Additionally, she checked to ensure our trip was progressing smoothly.
Here are some highlights:
Rome: We were greeted at the airport by our agent, who expedited our passage through passport control. The following day, we started our exploration at the Vatican. Our agent had purchased our tickets in advance, allowing us to skip the line. She also planned the remainder of our self-guided tours of the Colosseum, Roman Forum, and other ancient sights. We accomplished so much in just two days!
Florence: We took part in a pasta-making class with a chef who was fantastic! Her husband was also quite charming. Our experience there was truly wonderful. Special thanks to our driver, who was incredibly helpful and informative.
Sorrento (Amalfi Coast): We began with a visit to Pompeii, where our guide, also arranged by our agent, was spectacular! His passion and extensive knowledge made the experience enjoyable. Next, we had a fun blind wine tasting. When we arrived at our amazing hotel, we were greeted with a surprise.
While in Rome, we encountered a minor issue, which our agent resolved quickly. She even went above and beyond by ordering us a bottle of prosecco to celebrate. We also took a car tour of Positano and Ravello, guided by a local from Ravello who was informative, knowledgeable, and delightful. We loved her! Our day ended with a lovely sunset cruise off the coast! Both days had excellent drivers.
This trip was a dream come true for my husband and me. Without a doubt, our agent made it the luxurious experience we desired. I highly recommend her and her team!
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We loved the hotels you selected. The drivers were prompt and the guides were good. We especially loved our guide in Florence. Monterosso al Mare was beautiful.
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We had an amazing 2 weeks in Italy, from Rome, to Bari, Positano, Sorrento, and Naples. The planning and execution of our trip through Zicasso’s tour operator was flawless! They worked with me quite a bit in the planning phase to make sure this was going to be our dream trip.
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