Immersive Italy Vacation 2019: North to South

View of Florence, Italy with the Cathedral of Santa Maria del Fiore as the focal point
A 12 day trip to Italy & Vatican City 
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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.

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Most tours are customized for private travel.

General Information

View of the fountain in the Piazza Navona in Rome, Italy
Doge's Palace built Venetian Gothic style in Venice, Italy
View from a rooftop looking down upon beige buildings in the town of Bologna, Italy
View of one of the Two Towers (Le due Torri ) of Bologna, Italy
Upward view of the glass dome in Galleria Vittorio Emanuele II in Milan, Italy
Pair of Italian made women's handbags
Cathedral Santa Maria Del Fiore at Dusk in Florence, Italy
Woman painting and decorating a carnivale mask
Close up view of paintings of the Basilica di Sant'Apollinare in Classe in Ravenna, Italy
St. Peter's Basilica with sunlight peering through the clouds in the background in Vatican City, Italy
Close up of Trevi Fountain in Rome, Italy
Freshly made pasta resting in wooden bowl
Detailed Itinerary

Places Visited 

Milan, Venice, Florence, Bologna, Rome, Civita di Bagnoregio, Vatican City, Comaccio, Brenta Canal, Padua

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: 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 marks 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: airport transfer, accommodation

Day 2: 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 celebrates 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.

What’s Included: accommodation, tour, breakfast

Day 3: 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.

What’s Included: accommodation, transfer, tour, breakfast

Day 4: 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.

What’s Included: accommodation, tour, breakfast

Day 5: 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. 

What’s Included: accommodation, transfer, tour, breakfast

Day 6: 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.

What’s Included: accommodation, tour, breakfast

Day 7: 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.

What’s Included: accommodation, transfer, tour, breakfast

Day 8: 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.

What’s Included: accommodation, tour, breakfast

Day 9: 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.

What’s Included: accommodation, tour, breakfast

Day 10: 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 returns to Rome in April, welcoming the fast-pace and exciting skill drivers possess when circling the nearly two miles circuit over 19 laps. 

What’s Included: accommodation, transfer, tour, breakfast

Day 11: 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.

What’s Included: accommodation, tour, breakfast

Day 12: 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.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.