Immersive Italy Vacation: North to South

What to expect on this itinerary
Interweave luxury and culture, authenticity, and heritage during your custom-tailored Italy tour brimming with exclusive experiences. Wander the galleries of the Vatican with a guide before the doors open to the public, enjoy a simple pastry after witnessing the intricacies of Michelangelo’s David, explore the vast halls of the Uffizi Gallery after-hours and immerse yourself into the secrets of the Venetian Republic uncovering hidden histories akin to legend. Whether indulging in fashionable company in Milan or relaxing with a glass of delicious wine in Montalcino, your Italy vacation brings the best of La Dolce Vita’s many opulent pleasures.
Customizable Itinerary
Milan – Arrive in Milan with a Private Art Tour of the Fashionable City
Relaxed cafes are tucked between medieval buildings and structures adorned with 19th-century splendor are set among trundling trams and charming piazzas making famous Milan. Arrive in Milan at Malpensa Airport, where your private transfer greets you at customs and escorts you to a luxurious hotel near the fascinating soaring spires of the celebrated Duomo. The art of Milan inspires visitors and locals with historical proportions and grand designs, and your eyes will be working to take it all in as you arrive in the city.
2019 marked the 500th anniversary since the death of Leonardo da Vinci resulting in an Italian celebration spanning from Milan to Florence with great museums and majestic villas paying homage to the master artist, inventor, and architect. If visiting Milan in February, the Borsa Internazionale del Turismo will showcase the contributions of the Renaissance man at venues like Sforzesco Castle, the Ambrosiana Library and Art Gallery, and the Museum of the Vinciano Cenacolo displaying reproductions of a number of machines da Vinci designed.
What's Included:
Milan – Embrace Style with a Personal Shopper Experience and Tour
Venice – Travel the Brenta Canal to Venice for an After-Hours Art Visit
Venice – Enjoy the Secret History of Venice and Local Food Excursion
Bologna – Relish Comacchio before a Private Pasta-Making Class
Bologna – Delight in a Truffle Hunt and Enjoy a Ravenna Art-Walk
Florence – Venture to Florence for an After-Hours Visit of the Uffizi
Florence – Breakfast at the Academia before Florence at your Leisure
Florence – Indulge in Wine and Food at Montalcino and Pienza
Rome – Visit Fascinating Civita di Bagnoregio en route to Rome
Rome – Navigate Vatican City and the Hidden Gems of Rome
Rome – Depart for Home
Trip Highlights
- Visit the Sistine Chapel without the crowds with an exclusive tour of the Vatican Museum galleries before regular opening hours
- Bask in the attention and service of a personal shopper in the iconic city of fashion, Milan, visiting famous boutiques, including the first Prada store
- Delight in the complex flavors of Brunello di Montalcino wine during a private wine excursion through the Val d’Orcia in Tuscany
- Relish the distinctive flavors and elevated tastes of truffles shaved over traditional Emilia-Romagna dishes after a private truffle hunting tour
- Navigate the halls and fascinating works in the Uffizi Gallery during an after-hours tour away from the tourists to view artists like Botticelli
- Enjoy an early morning tour of the Accademia Gallery in Florence for exclusive access to Michelangelo’s iconic statue of David
- Discover the enchanting canals and preserved architecture of the 13 connected islands that make hidden Comacchio
- Embrace the magnitude of contemporary artwork on display inside the Guggenheim Museum in Venice with a private after-hours tour
- Witness the exceptional charisma of the vibrant colors and unique depiction of biblical characters in Leonardo da Vinci’s Last Supper
- Indulge in the warm glow and mesmerizing aesthetic of ancient Byzantine mosaics preserved in the churches and baptistries of Ravenna
Detailed Description
Savor your immersion into the heart and soul of Italy during your 14-day luxury tour with exclusive excursions perfect for discovering splendor around every corner. From fashion to art, architecture to archeology, the many faces of Italy shine behind the facade of cities and towns with welcoming extravagance. Devoted travelers will find delight in uncovering new and antique styles cast in the modern fashion capital of Milan and the ancient ruins of Rome, the Byzantine art of Ravenna and cooking traditions of cucina povera in Bologna. Your Italy vacation takes place at your pace in the way you always dreamed as you evoke the sophisticated charms of famous cities and classic charisma of the countryside.
Your exclusive exploration of Italy begins in Milan with your private transfer meeting you at the airport. The city brims with sensational art ranging from the architecture like the Duomo to the great works on display in the select art museums. Historical churches contain priceless artifacts like Leonardo da Vinci’s Last Supper, and the galleries offer insight into the styles of the past, present, and future offering shopping experiences in boutiques and with famous brands like the original Prada store. Move next to the Brenta Canal to explore the lavish heritage of the Venetian Republic along the waterway that connects Padua to the Venetian Lagoon lined with villas from the former aristocracy. Venice embraces its reputation as a city of extravagance showcasing marble palaces and divine artistic masters inside museums like the Guggenheim. The secret history of the city immerses you into the hidden chambers and prison cells of the Doge’s Palaces, as well as illuminating your taste buds with insight into the iconic flavors of the city’s cicchetti.
The region of Emilia-Romagna encapsulates the often overlooked magnetism in Italy with towns like Comacchio, known as the “Little Venice,” for its canals. Make fresh pasta and hunting for truffles to further understand the connection the region has with its cuisine and the delectable ingredients offered year-round. Bologna has become a gem of a regional capital with medieval arcades and cherished restaurants while the city of Ravenna boasts incredible gilded mosaics from the Byzantine era, as well as the tomb of epic poet Dante Alighieri. The emblematic region of Tuscany enchants you with verdant hills and radiant artwork in Florence by avoiding the crowds at the Uffizi and Accademia galleries touring after-hours and before the doors officially open, respectively. Traveling the picturesque countryside engages you in the treasured wine region of the Val d’Orcia at Montalcino and the enchanting Renaissance town of Pienza.
Traveling to Rome takes you through the countryside of Lazio and the small, nearly deserted town of Civita di Bagnoregio, located on a volcanic rock eaten away by the elements over the centuries. Finish with the city of Rome, which boasts the brilliance of the past and the wealth of Vatican City for a collection of mesmerizing fountains, grandiose piazzas, and elegant museums. Spend time in the Vatican galleries before they officially open to the public and uncover the secret wonders of the city including a hidden view of St. Peter’s Basilica. Read more here about the other exceptional experiences our travelers have appreciated in their travel reviews of Italy.
Starting Price
$4,300 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.
Verified Traveler Reviews
Based on 6971 reviews
Our trip was absolutely amazing and the planning done by Zicasso's travel company surpassed my expectations. The attention to detail was amazing: from excellent and punctual drivers to assistants who helped us with the water taxis in Venice to the lounge access for trains. It was truly white-glove service that made my trip seamless and allowed me to enjoy every moment because every detail was handled.
The excursions were fantastic. I especially enjoyed the cooking class at a farm in Tuscany and the Vespa tours in Rome. There was a nice mix of private excursions for the walking tours and boat rides, to a few shared excursions, such as the cooking class.
The hotels the travel company booked were chic, boutiquey Italian hotels and each had its own charm (from the former palace in Venice to the castle in Chianti), and we loved them. We would absolutely recommend to anyone booking a trip to Italy!
See more
Zicasso's team was excellent with planning and execution of the itinerary to meet our specific needs.
I was able to add an additional city on short notice!
We had knowledgeable local city guides and all drivers were professional.
We had a wonderful family trip!
See more
We had an excellent experience with Zicasso's travel company. We are a family of four and spent 18 nights going through Italy and France. We worked with the company to make arrangements to see the cities and sites we wanted to visit. They offered great options for hotels and activities. They stayed in close contact with us during the trip and made additional arrangements upon request. The company provided outstanding service making arrangements and during the trip. We were very satisified and have already recommended them to our friends.
See more
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!
See more
The trip went very well! Our Zicasso travel specialist did a thorough job planning our vacation to Italy. We would definitely use her again.
See more
Our trip was a 10 out of 10! There is no way it could have been any better. Zicasso's travel expert and the tour company's team were incredibly responsive (not that we had any issues) and the itinerary was so impeccably curated.
Every greeter, driver, and tour guide was incredibly knowledgeable and professional, and hotels were immaculate. It was such a relief to know that every last detail was taken care of and we didn't have to worry about anything.
We highly recommend our travel company and would definitely use them again.
See more