VIP Tour of Italy: A Signature Experience

A 16 day trip to Italy 
5 out of 5 stars
1 reviews

This is Italy with no-holds barred, an excursion of such incomparable luxury that it beggars description. Private tours of the Vatican Museum and after-hours visits to Venice’s St. Mark’s Basilica. Exclusive cruises along the famed Amalfi Coast and once-in-a-lifetime excursions to Bologna and St. Moritz. The biggest suites in five-star hotels and dinner at restaurants with multiple Michelin stars. Whatever your inclinations, this tour comes down to five words: Go big or go home.

Customize This Trip For Me
Most tours are customized for private travel.

Customers Who View This Tour Also Viewed
  • 4.75
    4.75 out of 5 stars
    4 reviews

    VIP Tour of Sicily: Beauty, Culinary & Luxury Experience

  • 4.75
    4.75 out of 5 stars
    16 reviews

    VIP Morocco Custom Tour: Exploration in Luxury

  • Balmoral Castle, the Royal Family's summer home, in Scotland.
    4.75 out of 5 stars
    4 reviews

    VIP Tour of Scotland: A Private Access Journey

  • 5
    5 out of 5 stars
    1 reviews

    VIP Romantic Getaway Tour to Fiji & New Zealand: A Private Excursion

General Information

The dome ceiling of the Florence Cathedral.
Castel Nuovo in Naples.
Detailed Itinerary

Places Visited 

Villa D’Este, Lake Como, Milan, Verona, Venice, St. Mortiz, Torcello, Florence, Bologna, San Gimignano, Siena, Rome, Vatican City, Ravello, Amalfi Coast, Capri, Li Galli Islands, Naples

Departure Dates 

Flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Beginning Your Italian Experience

Greet Italy at Malpensa Airport on the outskirts of Milan, where a private driver will be waiting to take you to the inimitable splendor for the Grand Hotel Villa D’Este in nearby Cernobbio on Lake Como. You’ll enjoy the unparalleled luxury of a Cardinal Suite, one of the best rooms in this exclusive and elegant hotel that also offers a sensational restaurant, a perfectly attentive staff, and views that will take your breath away. Throw in a world-class spa, and you can understand why this is one of the best hotels in Northern Italy.

Dinner tonight is at the ever elegant Veranda Restaurant, where you’ll enjoy fresh, creative and perfectly prepared Italian cuisine while you get a splendid view over the azure expanse of Lake Como.

Day 2: From the Shores of Lake Como to the Streets of Milan

After a delicious and hearty breakfast at the hotel, you’ll get the ultimate first-look at Lake Como as an expert guide ferries you to the area’s most attractive villages and towns. Start on Como’s western coast, taking in some of the most enchanting villas in the country, from the stunning gardens of Villa Balbianello to the opulence of the villas that line the lake. Pass some of the lesser-known towns on Como’s shimmering shore before exploring Bellagio and enjoying a unique and unforgettable lunch at Isola Comacina.

In the afternoon, you’ll travel back to the streets of Milan to get a rare and very special tour of the Refectory of the Santa Maria delle Grazie, where the incredible Last Supper fresco by Leonardo da Vinci dominates a wall where the faithful used to take their meals. After this amazing artistic interaction – led by an informative and engaging guide – you’ll enjoy a superb dinner at Ristorante L’Ulmet, one of the best in Milan, where the food is sublime and the wine list truly unmatched.

Day 3: Through the Alps to Switzerland

Bring your passports as your local driver takes you through the soaring Rhaetian Alps past the Italian frontier and into the dominion of Switzerland, bound for the sensational resort town of St. Moritz. The drive will lead you alongside Lake Como, its blue waters glistening in the morning sun, before you begin your ascent of the mountains and the crossing into Switzerland. Upon arriving in St. Moritz, spend some time cruising through the scenic streets of this beautiful city, enjoy a traditional Swiss lunch at one of the city’s many laid-back cafes or climb the nearby peaks to gain a spectacular vista over the breathtaking scenery that surrounds you. 

This evening, back in Italy, you’ll enjoy the fare of the Trattoria Navedano, where you can decide exactly what type of feel you want your meal to take on. Because at this restaurant, the owners have set up multiple rooms, each with different feels, each setting the perfect backdrop to incredible cuisine and undeniable charm.

Day 4: Across the North, Via Verona

Make your way east from the shores of Lake Como through the rugged landscape of the Italian north, bound for the shores of the Adriatic and the singular city of Venice. While en route, stop in the delightful northern town of Verona, the setting for Shakespeare’s immortal Romeo and Juliet and a fascinating community in its own right. You’ll certainly want to see ramparts and battlements on the Castel Veccio, as well as tour the incredible Arena Amphitheater, a Roman-era structure that still hosts performances of Verona’s opera company.

After a delicious lunch at Ristorante 12 Apostoli – thought by many to be the finest restaurant in the Veneto region – you’ll continue your journey to Venice, finally alighting at the Piazzale Roma. There, you’ll take a water taxi to your amazing accommodations at the Hotel San Clemente Palace, a five-star monastery-cum-resort-style hotel that is a few footsteps away from the famed Piazza San Marco. You can take a few hours to explore your immediate environs before setting out for dinner at the famous Harry’s Bar, a favorite spot of Ernest Hemingway and the original home of the Bellini cocktail and beef carpaccio. 

Day 5: Discovering the Mysteries of the Queen of the Adriatic

Today begins with a fully guided tour of the incomparable Floating City, winding your way through the labyrinthine canals and serpentine streets that slither through the metropolis. Your expert guide will show you the back alleys – or rather back canals – of Venice, the unworn paths that many tourists overlook, the nooks and crannies that hold the treasures that make this one of Italy’s greatest cities. You’ll explore Venice by land and by water, checking out the most beautiful churches, townhouses, and artwork that the city has to offer.

This afternoon, take an exclusive tour of St. Mark’s Basilica led by a guide who will be sure to give you all of the best details of this opulent church of gold. You’ll be free from the throngs of people to take your time, reveling in the amazing details that go into seemingly every square inch of this beautiful structure.

This evening, enjoy dinner at Ristorante Do Forni, where you’ll find traditional Venetian seafood mixed with gentle sauces and fresh produce, as well as service that is welcoming and friendly.

Day 6: The Environs of Venice

After a leisurely morning and a delicious breakfast, you’ll take a private water taxi to the immaculate island of Torcello, just in time to make your reservation for lunch at the Locanda Cipriani, where the food is simple and superb and the service is second-to-none. Enjoy the rich wood ceilings and the warm terra cotta bricks that dominate the scenery here before setting into classic Venetian fare re-done “Cirpriani style.”

After this delectable meal, the main islands of the Venetian lagoon await you, ready to showcase their artisanal wares and the darling communities to all passersby. Explore Murano, Torcello and Burano as a knowledgeable guide tells you about these islands’ storied history and their cultural impact, and where you can pick up some of the fine handicrafts that can be found throughout the islands. Murano is particularly known for its glasswork, while some of the best lace in the world is made in Burano.

Day 7: A Traipse Through Italy’s Culinary Heartlands

Return to the west of Italy as today sees you leaving Venice and bound for Tuscany, passing through rustic Italian scenery and past noble and fascinating villages. Stop in Bologna in the mid-morning to discover all that this city has to offer, from the campus of the world’s oldest university to the striking edifices and delightful streets of the historic city center. You’ll even get the chance to enjoy a meal in one of the best foodie towns in Italy, as you have reservations for lunch at the Ristorante Franco Rossi, where two different menus – one based on seafood and one based on food from land – offer a myriad of creative and delicious options, perfectly complemented by a wonderful wine list.

Alight in Florence, where you’ll spend your nights in the Hotel Lugarno, within eyeshot of the famous Ponte Vecchio and offering a fantastic view over the gently rolling River Arno. You’ll find the staff is attentive and courteous, the facilities modern and elegant, and the location simply unbeatable, as it offers the perfect place to base your excursions into Florence.

Dinner this evening is at the Cavolo Nero Restaurant, a small, secluded spot that serves outstanding traditional Italian food with perfect service. This is a restaurant that always delivers fine fare and an unforgettable dining experience.

Day 8: The Capital of the Italian Renaissance

Today is stuffed with Florentine adventures, as you’ll walk the streets of this famous city where the air is thick with the remnants of artistic genius. Begin at the bustling Piazza della Signoria, the traditional city center, fronted by the immense and imposing Palazza Vecchio, where the city’s ruling class met to made city-wide decisions. Continue on to the Piazza del Duomo, where Giotto’s brightly colored campanile and Brunellschi’s soaring dome highlight the beautiful church of Santa Maria del Fiore. Don’t forget to check out the baptistery doors, executed by Lorenzo Ghiberti and dubbed “the Gates of Paradise” by Michelangelo himself.

Check out the remains of some of Italy’s greatest names at Santa Croce, as Machiavelli, Michelangelo, Galileo and many more are all laid to rest here, before returning to the shores of the Arno and the alluring Ponte Vecchio, where some of the best jewelers in Florence have set-up shop. The day ends with some relaxation at the hotel and dinner at the outstanding Trattoria Omero, one of the true hidden gems of Florentine cuisine. Here, the mains are hearty and filling, the desserts are decadent, and the drinks are always perfectly selected.

Day 9: The Masterpieces of the Uffizi

This morning, discover the many magnum opuses that fill the halls and walls of the unmatched Uffizi, one of the best art galleries in Europe and arguably the foremost collection of Renaissance art in the world. Enjoy the best efforts of legends like Caravaggio, Botticelli, and da Vinci, before exploring the astounding Vasarian Corridor, the hidden passage used by the Medici to spirit them from their home at the Pitti Palace to their “office” at the Palazza Vecchio. This is a side of this famous structure that few know about and even fewer get to see, and it is a truly one-of-a-kind experience. If you like Italian art, you may find the Italy art tour interesting.

Take the afternoon to enjoy Florence on your own. Maybe shop for some of the fine leather goods that fill the city, or simply spend some time on the patio of a nearby café sipping an espresso drink, before heading to your fabulous dinner at the Enoteca Pinchiorri. This restaurant is home of the best wine cellar on the continent and a menu that features French-Italian fusion dishes that are sublime as they are creative.

Day 10: Through Tuscany to the Capital

Bid adieu to the banks of the Arno and travel south to the streets of the Eternal City – Rome. Along the way, you will stop in two of Tuscany’s best-known and best-loved towns to get a true sense of life in this tremendous region of Italy.

First up is Siena: a medieval town that has one of the most picturesque squares in Italy, Il Campo. Not just beautiful, it’s also home to the famous Palio, a twice-annual bareback horse race that is run through the streets of Siena. Next, you’ll visit the tower-filled town center of San Gimignano, the site of a Renaissance arms race that resulted in the skyline being dominated by scores of proto-skyscrapers, reaching like teeth into the blue Tuscan air.

Finally, you’ll arrive in Rome and check into your accommodations at the St. Regis Hotel, Rome’s first deluxe hotel and one of the most famous establishments in the city. It’s right in the middle of all of Rome’s best spots, with the Trevi Fountain, the Spanish Steps, and the Via Veneto all beckoning you with their nearness. This is where foreign dignitaries and diplomats stay, the preferred hotel of celebrities and royalty, and you’ll have no trouble understanding why. The restaurant here, Vivendo, is also truly extraordinary and was named the number one restaurant in all of Rome by Zagat.

This evening, enjoy dinner at George’s Restaurant, where Chef Antonio Sciullo prepares his menu with a careful eye to the seasons, ensuring the freshest and most creative food you’ve ever had the opportunity to try. There are more than 1,200 wines in the cellar, and the dining rooms have been done up in lavish style, offering diners serenity and peace while they enjoy the culinary marvels unfolding before them.

Day 11: The Relics of the Eternal City

There are few cities on the planet that can match the majesty and history of puissant Rome, and today is dedicated to discovering all the highlights of its noble and notorious past. Start at the Roman Forum, which was the major public meeting place in Ancient Rome and is where you’ll get a view of the remains of the Roman Senate as well as the Basilica of Constantine. After, head next-door for an in-depth look at the iconic Colosseum, one of the most indelible images of the grandeur of the Roman Empire. Enter the venerable church of St. Peter in Chains to see Michelangelo’s triumphant statute of Moses (meant to decorate the tomb of Pope Julius II) before visiting the cavernous Basilica of St. Peter and enjoying a drive past the immense Circus Maximus up Palatine Hill, the legendary founding place of the city.

Later this afternoon, you’ll get a private visit to the Vatican Museums and the sensational Sistine Chapel, led by a guide that knows the Vatican better than most cardinals. Make your way through the incredible collection of the museums – you’ll be sure to enjoy Raphael’s famous work The School of Athens – before ending your tour in the awesome presence of the frescoed ceiling of the Sistine Chapel, one of the greatest artistic achievements of any age. 

Dinner tonight is at Le Pergola, the only restaurant in the city to receive two Michelin stars, highlighted by exceptional service, spectacular food, and a rooftop terrace that boasts the best views of the city. 

Day 12: Relaxing in Roma

Today is yours to enjoy the pleasures of Rome as you see fit. Head to the Piazza Navonna to enjoy a cappuccino and some of the best people watching in the city, or check out the exhibits at one of the city’s excellent museums. The Capitoline Museum, for instance, sports an impressive assortment of ancient statuary – including a cast of the famous Capitoline Wolf, the she-wolf that allegedly nursed the legendary brothers Romulus and Remus – while the National Gallery of Modern Art has the largest collection of works by Italian modern artists in the world, as well as a number of pieces from foreign masters. You might also want to do some shopping at the famous Via Condotti, considered the best spot in Rome for haute couture. Make sure you stop by the Caffe Grecco before leaving, as literary legends, heads of state, and even Casanova are said to have frequented this coffee shop, the oldest in the city.

Day 13: From Ancient Glories to Breezy Shores

Your last days in Italy are spent in the serene splendor of the southern shores of the Mediterranean, bound for Ravello on the beautiful Amalfi Coast. On your way south, you’ll stop for lunch at Ristorante Don Alfonso, where the food is outperformed only by the attentive and personalized service, where the 25,000 bottles of wine can be carefully sifted through with the help of an expert sommelier, and where the meal takes a backseat to the entire dining experience.

Once in Ravello, you’ll check into the Hotel Palazzo Sasso, a new five-star hotel that perches prominently and features envy-inducing views of the stunning Amalfi Coast and the crashing surf of the Mediterranean. Situated in a former Italian villa, this hotel has consistently been rated one of the best hotels in the country and, indeed, the world; the suites are large and offer stupendous amenities, the spa has a myriad of incredible treatments, and the restaurant has received two Michelin stars. This is sure to be a stay that you will never forget.

Day 14: The Jewel of Southern Italy

Wind your way through some of Italy’s most dazzling scenery as you spend today in and around the eye-catching and breathtaking Amalfi Coast. Start at the town of Amalfi, where you can admire the beautiful cathedral and its Cloisters of Paradise, a shining example of Norman and Arabic architecture in Italy, before continuing on to Ravello. It is in Ravello where you’ll find the best sweet pastries in the region and where you can find the spectacular Villa Rufolo, a 13th-century mansion that charmed the heart of Richard Wagner with its gorgeous gardens and miraculous view.

This evening features an eating experience unlike any you’ve ever known, as the renowned cook Mamma Agatha fetes you personally with her own hearty, filling and comforting food. As you enjoy the heart and soul that went into preparing these dishes, you can think about the illustrious company you find yourself in, as Agatha has also cooked for film stars and first ladies, European royalty and American celebrities. 

Day 15: One Last Day on the Italian Peninsula

One final hurrah awaits you today, a day of exploration and adventure, a day of discovery and pure, unadulterated natural beauty, for today, you set out for Capri, the play place of emperors and aristocrats for centuries. You’ll board a private yacht that will show you all of this amazing coastal region, treat you to a delicious lunch and introduce you to the charming towns that dot the landscape. Stop by the stunning Li Galli Islands before setting out for Capri, where you can walk the ruins of the former imperial villas or marvel at the beryl glow of the famed Blue Grotto.

This evening sees you bidding farewell to Italy and your fellow guests as you enjoy one last go at authentic Italian cuisine at Rossellini’s, an Amalfi establishment that is sure to leave your stomach and heart equally satisfied.

Day 16: Returning Home

Today, a private driver will take you to the airport in Naples, where you’ll board the plane that will see you back to your home country. As you reminisce upon the past two weeks, these 16 incredible days that saw you traverse this amazing nation, you’ll find yourself smiling at the fun of the past and planning for the fun of the future. 


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.
Customers Who View This Tour Also Viewed
  • a bridge and buildings with their lights on with a river at dusk
    5 out of 5 stars
    1 reviews

Historic Cities to Treasured Coastline of Italy Tour: Rome, Naples & Sorrento

  • 5
    5 out of 5 stars
    1 reviews

    8 Day Luxury Tour of Sicily Highlights: Taormina, Syracuse, Agrigento, Palermo

  • 4.85603
    4.86 out of 5 stars
    771 reviews

    Escorted Art, Food, and Culture Tour of Italy

  • 4.96183
    4.96 out of 5 stars
    131 reviews

    A Complete Italian Experience: Florence, Tuscany, Cinque Terre & Rome Tour