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...
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.
Milan – Embrace Style with a Personal Shopper Experience and Tour
Your guide greets you at your hotel after breakfast eager to introduce you to the splendors of Milan beginning with a personal shopping excursion at the stunning Galleria Vittorio Emanuele II. The sensational work of architecture was built between 1865 and 1867 as Milan’s first shopping arcade. The central octagonal glass dome allows plenty of light to pour over the mosaic floors standing nearly 158 feet tall. The decorative floor beneath the glass dome portrays the coat of arms from the three capitals of Italy representing Turin, Florence, and Rome, in addition to Milan’s. Your personal shopper will aim to understand your preferred flourishes and style while also taking a special interest in the ways to accentuate your best features starting at the original Prada inside the gallery.
Mario Prada started the company in 1913 before the meteoric rise in popularity resulted in a fashion icon acting as the official supplier of clothing to the Italian royal household in 1919. 2019 celebrated the 100th anniversary of Prada’s connection with the Italian royal family signified by the company label, which uses the knotted rope officially associated with the Italian royal family’s coat of arms as the frame for the company logo. The store retains a sense of its illustrious history and celebrated elegance with handmade shelving units made from mahogany and displaying exquisite handbags, trunks, footwear, and clothing. Alongside your guide, you can learn more about the history of Italian fashion before an afternoon spent enjoying it all.
Venice – Travel the Brenta Canal to Venice for an After-Hours Art Visit
Your private transfer meets you early in the morning and will escort you away from the bustling streets of Milan bound for the serene cobbled lanes and vibrant university ambiance of Padua. Byzantine domes accentuate the skyline above the blossoming flowers of the world’s first botanic garden and the distinctive anatomy theater.
You will board a boat on the Brenta Canal, a waterway spanning over 16 miles connecting the former colony of the Venetian Republic with the Venetian Lagoon. Aristocrats of the republic built elaborate villas along the water’s banks enjoying the escape from the crowded city and the easy access to and from the lagoon. Stop at a number of villas including Villa Foscari, which was erected along a bend in the canal. Weeping willows frame the façade designed in the mid-16th century while the interior contains the unique decorations of painted architectural elements as well as grand frescoes depicting allegorical figures from Ovid.
Upon reaching Venice, you will have an exclusive after-hours tour of the Peggy Guggenheim Collection introducing you to the intersection of Venice’s history and modernity. The fascinating museum was placed inside an unfinished 18th-century villa overlooking the Grand Canal in 1951. Enjoy the effervescent tickle of a glass of Prosecco at your arrival before entering the galleries of the private collection amassed by the famous American heiress through friends, critics, and associates. You marvel at the subtle, still beauty of Giorgio dei Chirico’s Red Tower, an enigmatic work of a dreamlike atmosphere from an irrational perspective.
Venice – Enjoy the Secret History of Venice and Local Food Excursion
Venice is a city of mystery and intrigue decorated with lavish palaces and serene canals, arching bridges and the bulbous domes of St. Mark’s Basilica. Narrow streets lead to hidden piazzas scattered among the six neighborhoods known as sestieri. Your guide will greet you in your hotel lobby after breakfast before introducing you to the city’s morning charm stemming from the vivacious activity at the Rialto Market. Uncovering the secrets of Venice lead you to the Doge’s Palace beginning in the sunny courtyard facing a narrow door. The entranceway leads into the damp cells of the official prisons used during the Venetian Republic where Giacomo Casanova was once held. The thick stones retain their moisture in the dim light.
Climbing out of the cellar leads you through the Bridge of Sighs, the iconic walkway adorned with Venetian Gothic style. The name of the bridge derives from a translated poem by Lord Byron, in which the narrator describes the sigh prisoners make when viewing their beloved city for the last time on the way to prison. You look out the same window as those fictional characters enjoying the way the bridge frames the Ponte dei Sospiri, passing gondolas, and the St. Mark’s Campanile in the distance. You continue into the discreet chambers of Sala del Consiglio dei Dieci, in which the secret state court would pull the strings of public and private life in the Republic.
In the evening, your guide leads you once more down the winding, labyrinthine streets of Venice this time following the enticing aroma of delicious local specialties. Wine bars across the city known as bicchieri serve small plates to accompany the drinks often accentuating the flavors of both the wine and food. The variety of little dishes reveals a selection of fried meatballs and bite-sized crostini topped with sardines cooked in onion and vinegar. Locals typically order a wine from the Veneto region in which Venice is located including popular sparkling Prosecco and the less-known peppery spice of Raboso.
Bologna – Relish Comacchio before a Private Pasta-Making Class
The allure of Venice’s canals stays with you as you travel away from the lagoon and outside the region of Veneto into Emilia-Romagna. Before reaching Bologna, you can stop in the enchanting town of Comacchio, often referred to as “Little Venice.” Unlike the more famous city on the lagoon, Comacchio retains its sense of authentic charm endowed with the calm surface of meandering canals fed by the Po Delta. Seven beaches shine with golden sands and crisp pebbles while countless bridges arch over the waterways connecting the 13 separate islands and offering fantastic views of the town.
Bologna hides the modernity of high-tech startups and engineering behind a façade of medieval architecture and an endless love affair with food. Colonnades contain exuberant cafes, and red brick tiled roofs surround Piazza Maggiore. Two grand towers reflecting the former wealth of the city’s aristocracy now list from age with Torre Garisenda leaning four degrees off its original axis. You will meet your private chef after settling into the comforts of your luxury hotel in the heart of historical Bologna learning how pasta made fresh with eggs sits at the center of Bolognese cuisine.
Your chef is known as one of Le Sfogline, a consortium of women famous for making and pulling pasta by hand. You will mold the flour into a volcano shape and crack the egg inside the crater quickly mixing the egg and flour together. Shape the dough before flattening it with a rolling pin. Your chef shows how folding the dough in a certain way before cutting it into strips creates perfectly symmetrical tagliatelle strips.
Bologna – Delight in a Truffle Hunt and Enjoy a Ravenna Art-Walk
Emilia-Romagna’s obsession with flavor peaks in the morning during your private hunt for truffles. You will follow your guide and their dog into the depths of woods near the Portico of Romagna, a 14th-century village with Roman roots. The moisture in the forest floor supports the growth of the treasured tuber along the roots of various trees like oak, maple, elm, pine, and chestnut. They can grow deep underground, which is why the hunter uses dogs who can sniff-out the fragrant ingredient up to three feet below ground.
The scent of pine fills the air before the dog digs beneath a towering tree. You can help the hunter unveil a black truffle before returning to their home for a delicious lunch featuring the ways the simple, fresh ingredient can elevate a traditional dish. The scent of fried eggs becomes a sensational earthy delight with the addition of shaved truffle while passatelli pasta cooked in a broth and parmesan acts as the perfect base for a truffle topping.
Move next to the city of Ravenna, which stands out from the neighboring towns of Emilia-Romagna with a history steeped in Byzantine character deriving from the centuries during which the city acted as the capital of the Western Roman Empire. While much of the Italian peninsula staggered after the fall of the Roman Empire, Ravenna thrived as a center of artistic, philosophical, and architectural expression. A remarkable number of mosaics have survived more than 1,500 years leading you to the exceptional Basilica di Sant’Apollinare Nuovo. Spend the rest of the day exploring all that this beautiful region has to offer.
Florence – Venture to Florence for an After-Hours Visit of the Uffizi
The Birthplace of the Renaissance shines along the banks of the Arno River with a skyline known for captivating visitors with orange roof tiles, soaring bell towers, and the fascinating brick dome of the cathedral designed by Brunelleschi. The cobbled lanes of the historical city center wrap around the Piazza del Duomo with museums and churches overflowing with priceless art. The cinematic ambiance of the city derives from the preserved 15th and 16th-century palaces, and your guide takes you around the fascinating narrow lanes and vibrant piazzas leading to the daily market at San Lorenzo. Shops display leather shoes, coats, and bags, while vendors along the road offer gloves and scarves.
Venture into the famous Uffizi Gallery after-hours for an insightful excursion into the cherished collection of artworks spanning the 13th to 18th centuries. Cosimo de Medici I funded the construction of the palace in the 16th century to house the local magistrate before the public galleries opened in 1765. Avoid the crowds of the enchanting museum hosting famous work by the likes of Michelangelo, da Vinci, and Raphael.
Florence – Breakfast at the Academia before Florence at your Leisure
Before breakfast, you will meet your guide and enter the magnificent halls of the Accademia Gallery. The city remains at rest around you offering a different perspective of white, green, and pink marble of the Duomo glinting in the returning sunlight. Your exclusive tour of the museum allows you entrance before regular hours for an exciting introduction to the artwork on display. The gallery opened in 1784 as a space to display Michelangelo’s renowned sculpture, David. The mesmerizing sculpture stands 17 feet tall at the end of a long hallway.
Walking to the base of the figure feels like a slow procession lined with the unfinished sculptures meant to depict slaves for the tomb of Pope Julius II della Rovere but instead resemble prisoners trapped in stone. David has an elegant statue captivating you with a glance deriving not only from his size but also the intricate detail featured in the sinewy muscles and poignant stare. The drama of the episodic biblical tale captures the moment before the warrior steps into battle with Goliath. After spending time with the breathtaking artwork, you can continue to breakfast at a local café with the aroma of fresh espresso accompanied by the sweet scent of brioche stuffed with pistachio cream.
Florence – Indulge in Wine and Food at Montalcino and Pienza
As you travel through the Tuscan landscape between Florence and Montalcino, your driver can point into the distance at the town of Vinci, the birthplace of Leonardo da Vinci. The countryside contains the picturesque lushness for which Tuscany is known with rolling hills and rows of cypress trees, vast olive orchards and long stretches of vineyards. The town of Montalcino remains a charming gem immersed on the Sienese hills producing the decadent flavors of Brunello wine. The preserved 14th-century architecture on the hills of Val d’Orcia retain their ornate medieval charisma amid narrow, steep streets leading to a fabulous panorama sweeping across Tuscany. Restaurants and wine bars resemble large cellars serving authentic local delicacies.
A vintner welcomes you into a private cellar to learn more about the Brunello di Montalcino, a wine made from 100 percent Sangiovese grapes. The wine is treasured for its slow maturity improving as the years pass. The label of the wine can is safeguarded by the DOCG—controlled designation of origin guaranteed—protecting both consumers and producers from imposters. The vintner opens a bottle and pours you a sample of a newer vintage with the aromas of chopped herbs, woodland berries, and leather leading to flavors of black fruit and cocoa.
Once you reach Pienza, you find a fascinating city steeped in the harmonious theory of the Renaissance in the form of uniform architecture. As the home of Pope Pius II, the city was renovated from its medieval aesthetic in the mid-15th century developed into a jewel of the Tuscan landscape circling around the grandeur of Piazza Pio II. The public square embodies sophistication and elegance with a unique sense of perspective bordered by magnificent facades like Palazzo Piccolomini and the cathedral.
Rome – Visit Fascinating Civita di Bagnoregio en route to Rome
The rolling hills of Tuscany soon shift into the mixture of plains, foothills, and mountainous terrain of Lazio before you reach Civita di Bagnoregio, often referred to as “The Dying City.” Perched atop the dramatic plateau of a volcanic tufa rock, the town retains a picturesque ambiance above the unstable layer of clay and sand. A fascinating 984-foot bridge connects the towering rock formation to the hillside as if the town floats above the valley in the background.
Upon reaching Rome, you will find grandeur in the Eternal City and how it has evolved through time to connect with the aesthetics of shifting powers. The mix of haunting ruins and grand palaces, elegant artwork and fascinating legends engages with the vibrant energy of modern life. The remainder of the day is yours to enjoy the glowing majesty of Rome at your preferred pace, finding comfort in the historical city center with the sounds of trickling water emanating from the favored Trevi Fountain. The magnificent design features Oceanus, god of the sea, at the center of the water feature with horses sprouting from below creating a sense of symmetry. In 2019, the electric car race known as Formula E returned to Rome in April, welcoming the fast-pace and exciting skill drivers possess when circling the nearly two miles circuit over 19 laps.
Rome – Navigate Vatican City and the Hidden Gems of Rome
You will rise early in Rome as the sun barely glimpses over the magnitude of the Colosseum to meet your guide beneath the soaring dome of St. Peter’s Basilica. Michelangelo designed the incredible feature between 1547 and 1585 reaching 448 feet above the floor. Your exclusive tour of the Vatican Museums begins with meeting the clavigero, the staff member known as the keeper of the keys who has the privilege of opening the doors to the galleries each morning. You will enter an hour before the crowds for tranquil tour during which you feel alone with the breathtaking artwork and artifacts on display.
Pass through the Gallery of Maps where the right and left walls project the geography of the Italian Peninsula using the Apennines as the natural border dividing the east and west between the walls. After walking the galleries, you will arrive in the Sistine Chapel at the end of the tour for a rare moment of peace inside the famous religious center. The artwork stares down at you from all directions including the ceiling where Michelangelo painted a collection of masterful frescoes depicting the Book of Genesis. The master craftsman painted the ceiling between 1508 and 1512 leading to the elements of the larger scheme along the wall reflecting The Last Judgement. The nine scenes emanate from the central moment of the Creation of Adam, with to allegorical figures reaching their fingers toward each other.
After discovering the beauty of the Vatican without the clamor of the crowd, you can continue into the depths of Rome for insight into the remarkable splendor passing between Piazza Navona to Aventine Hill. On the hillside, which once acted as the outlying district for the poorer ancient Roman citizens, your guide will lead you to the Knights of Malta Gate for a secret view of St. Peter’s Basilica. The complex hosts one of the last surviving orders of the knights remaining from the crusades. Look through the antique keyhole where the wide lens frames the dome between the line of hedges for a unique perspective with purposeful design.
Rome – Depart for Home
The morning light shines through the oculus at the center of the Pantheon’s nearly 2,000-year-old dome. The fascinating architectural design was erected in the 2nd century AD and has continued to inspire artists like Michelangelo and Brunelleschi, who sought to recreate the captivating rotunda in their own works resulting in the style of St. Peter’s Basilica and Florence’s Cathedral respectively. The 16 massive pillars supporting the portico radiate grandeur and power before the marble floors embody a touch of exuberance once belonging to the ancient temple and the later church. After a morning adventure to take in as much as you can of this beautiful city, your private transfer will greet you at your hotel to escort you to Fiumicino Airport for your flight home and bringing an end to your exclusive exploration of Italy.
- 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
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.
$3,295 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.
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Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
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