Luxury Italy Tour in 14 Days

St Mark's Basilica in Venice, Italy

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.

Countries Visited

Italy, Vatican City

Places Visited

Milan, Como, Venice, Florence, Pisa, Lucca, Rome, Vatican City, Sorrento, Pompeii, Bellagio, Verona, Murano, Monterosso al Mare, Vernazza, Manarola, Riomaggiore, Corniglia, Amalfi, Ravello, Positano, Vietri sul Mare, Minori, Assisi

Suggested Duration

14 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Day 2

Como – Lakeside Como to Visit the Surrounding Towns

Day 3

Como – Beauty around Lake Maggiore and Borromean Islands

Day 4

Venice – After-Hours St. Mark’s Basilica Tour

Day 5

Venice – The Canals of Venice and the Island of Murano

Day 6

Vernazza – Famous Cinque Terre by way of Lovely Verona

Day 7

Vernazza – Prominent Trail Connecting the Towns of Cinque Terre

Day 8

Florence – Remarkable Pisa and Lucca before Arriving in Florence

Day 9

Florence – Art and History in the Uffizi and Accademia Galleries

Day 10

Rome – Beauty of Assisi before an Introductory Tour of Rome

Day 11

Rome – Sensational Art and Unique History of Vatican City

Day 12

Sorrento – Vast Ancient Pompeii en route to Sorrento

Day 13

Sorrento – The Natural Splendor of the Amalfi Coast

Day 14

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)

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 1044 reviews

Italy Trip Review: Rome, Florence, Tuscany, Cinque Terre, Venice, Pizza-Making Class, 2 Weeks

We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.

The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.

The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.

One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.

Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.

While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!

Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.

Every experience felt personal, meaningful, and special.

This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!

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Italy Tour Review: Milan, Lake Como, Bologna, Ferrari Museums, Winery Visit, Food Tour, Cooking Class, Boat Ride, 12-Day Trip

Zicasso's travel specialist organized an amazing 12-day series of private tours, taking us from Milan to the lake regions (Como, Maggiore, and Garda) and down to Bologna. Our days were filled with visiting churches, museums (including the Ferrari and Enzo Ferrari museums), a winery, parmigiano, prosciutto, and traditional balsamic manufacturing, a cooking class, boat tours, and food tours.

Along the way, we saw testing at the Ferrari track and a small portion of the women’s Giro d’Italia. With all that, we still had sufficient downtime to search the streets to find our own gems.

Our trip coordinator checked in with us daily to confirm the daily itinerary and transportation. When we had questions or needed to make a change due to the weather, she was thorough, attentive, and responsive in a way that was reassuring and comforting. She was simply amazing.

I would highly recommend using this travel specialist and team for any of your Italian travel needs.

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Italy Tour Review: Amalfi Coast, Ravello, Positano, Florence, Rome, Siena, Winery Visit, 11 Nights

Overall, the trip was perfect! The hotels were really nice and the itinerary was great.

A few things I would have changed. First, the Amalfi tour day. There was not enough time in Ravello or Positano. We needed more time to relax and shop.

The class of train could have been nicer for the Florence-to-Rome portion of the trip.

We've been to many wineries throughout Europe and the one we went to on our way to Siena was okay, but we have been to much nicer wineries, with better wine and food tastings. It was not a great wine tour experience.

Everything else was wonderful and we really enjoyed the trip with our sons!!!

Thank you!

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Italy Trip Review: Naples, Amalfi Coast, Sorrento, Capri, Positano, Rome, Boat Ride, Cooking Class, Wine Tasting, Colosseum, 12 Days

I recently completed an incredible 12-day vacation in Italy, arranged by Zicasso’s travel company, and it was one of the best vacations I have ever had. From the initial planning with the travel specialist and her team to the seamless execution on the ground, everything exceeded my expectations for a luxury custom trip.

We started in Italy, where we were immediately met at the airport by a hostess who got us through all the lines in record time and into a Mercedes Sprinter van that took us to Naples. Naples offered us a really vibrant, authentic Italian feel, and the incredible food that the travel specialist recommended from the movie "Eat Pray Love" was the best pizza I’ve ever eaten in my life. I don’t think I can eat pizza in the United States anymore. The private drivers and guides made this whole trip stress-free.

Our next incredible experience was the dream-like Amalfi, Sorrento, and the Isle of Capri. The hotel in Positano was beautiful. We were enchanted with all the colorful cliffs, the boutique shopping, and the stunning view from our balcony room. Sorrento was my favorite city of all. It was very relaxed, with lemon groves everywhere and beautiful sunsets, and our hotel had balconies that opened up on the Mediterranean. The highlight of our trip was the island of Capri. The boat ride was just fantastic and we started at the top of the mountain and did the chairlift so we had a whole view of the city.

The highlights of the trip for me were the boat ride along the Amalfi Coast, the cooking class and wine experience at the female venture, and the wine by Mount Vesuvius.

Our last two nights were back in Rome and it was kind of hard to go from the low-key vibes of Sorrento to the action-packed atmosphere of Rome, but the hotel the travel specialist picked was just perfect. It was 10 minutes from the Spanish Steps and she arranged a tour of the underground Colosseum. I learned so much about everything in that area. All the guides, the drivers, everything was magical. I would highly recommend this travel specialist and the travel company.

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Italy Vacation Review: Como, Lugano, Bellagio, Varenna, Lake Como, Boat Ride, Food Tour, 5 Nights

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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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.

34,000+ Verified Traveler Reviews