Italy Luxury Travel: Custom Vacation Package

A 10 day trip to Italy 
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This is an Italy tour for those who love fine food, from southern Italian specialties to the seafood of the Adriatic. It’s a vacation for those who stay only in the best hotels, from a lakeside resort that was the home of royalty to a hotel that houses a Michelin-starred restaurant. It’s a trip for those who want to experience Italy at its best, and it’s sure to be a trip you remember forever.

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Most tours are customized for private travel.

General Information

The Roman Forum.
Detailed Itinerary

Places Visited 

Rome, Positano, Capri, Sorrento, Ravello, Pompeii, Milan, Villa d’Este, Bellagio, Venice, Verona

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Arriving in Italy

Land in Rome, the capital of Italy and one of the most famous cities on Earth, where a private driver will transfer you to your elegant hotel in the picturesque village of Positano, gracefully perched along the hills that lead down to the surf of the famed Amalfi Coast. You’ll stop for lunch at Le Sirenuse, a Michelin-starred restaurant that features fresh seafood and produce presented in a dashing and elegant way, before checking in at your hotel in Positano, where you’ll have the rest of the afternoon at your leisure. A stroll along the beach is always an enjoyable and festive one, and the church of Santa Maria Assunta offers a magnificent dome composed of majolica tiles; inside is a Byzantine icon of a black Madonna that dates from the 1200s.  Dinner this evening is at the sumptuous Ristorante Max, where the terrace beckons you with its perfect weather and one-of-a-kind dining experience.

What's Included: transfer, dinner, accommodation

Day 2: A Resort Town Fit for an Emperor

Head to the docks to meet the captain who will lead on your own private journey from the shores of the Sorrentine Peninsula to the famed island of Capri, a resort to emperors since the glory days of the Roman Empire and Senators when Rome was still a republic. You can explore the ancient ruins of the Imperial villas, or discover the enchanting and mystical beauty of the Blue Grotto, where the sunlight shines through the seawater to create a sapphire glow that fills the sea cave. You can get great views over the island at the Belvedere of Tragara, where the villas of some of the wealthiest residents can be found, or turn to the town of Capri to discover the ancient Marina Piccola – used by Emperors Augustus and Tiberius – and the elegant hotels that line the streets on the Marina Grande. The evening sees you back in Positano to enjoy a delicious and elegant dinner at one of the town’s best restaurants: Le Sirenuse.

What's Included: breakfast, transfer and private tour to Capri, dinner, accommodation

Day 3: A Day on the Coast, A Night of Elegance

Wind your way west through the Sorrentine Peninsula until you reach its namesake town of Sorrento, where visitors and locals alike are always afforded unbeatable views over the Bay of Naples and up to the rising heights of towering Mount Vesuvius. You can explore the bustling scene at the Piazza Tasso or make your way to the excellent shopping on Via San Cesareo before stopping for lunch at Il Buco to enjoy traditional southern Italian food done right. Be sure to enjoy a spot of limoncello, the local digestif made from sweetened lemon rinds, after the meal; not only is it a specialty of Sorrento, it’s a delicious, sweet end to a savory meal.

The afternoon sees you returning through the southern Italian countryside to your hotel in Positano, ready for an evening of high style as you set out to nearby Ravello, a village of breathtaking beauty and a vibrant cultural scene. You’ll enjoy a delicious dinner at Palazzo Sasso, an elegant establishment where the service is unparalleled and the views over Ravello will take your breath away. After dinner, you’ll take in a concert in the unmatched ambience of the Villa Rufolo, which inspired sections of Boccaccio’s Decameron and moved Richard Wagner so much that he never forgot it. The evening is back in Positano.

What's Included: breakfast, transfer, dinner, concert, accommodation

Day 4: The Remarkable Ruins of Famous Pompeii

Pompeii is a place so steeped in history and surrounded by intrigue that it needs no further description. It was once a bustling city center in the heart of southern Italy, set beneath the shadow of a massive but seemingly benevolent peak they called Vesuvius, but every one now knows its name because of the catastrophic events of 79 AD, when the city was covered by the explosions of mighty Vesuvius. 

Ignored for centuries, abandoned for millennia, it wasn’t until the middle of the 18th century that the buried remnants of Pompeii were rediscovered, perfectly preserved in the fiery furnace of ash and searing air. There are people in their homes, seemingly asleep, as if unaware of what was going on around them; there are the immaculately preserved mosaics that fill the homes of wealthier citizens and line the public spaces. You will see it all, and learn all about the history of this fascinating area, before returning to Positano for a sumptuous evening meal at Donna Rosa.

What's Included: breakfast, transfer, dinner, accommodation

Day 5: The Shores of Lake Como

This morning sees you leaving the stunning coasts of southern Italy and turning north, bound for the charms of the north and the scenic coast of famous Lake Como, home to some of the toniest towns in the country, villages whose names have become synonymous with elegance. After flying from Naples to Milan, a private driver will transfer you from the airport in Milan to your hotel at the unmatched Villa d’Este, one of the finest hotels in the world and the former residence of royalty and artists alike. 

After a delicious lunch at the Veranda Villa d’Este, you’ll have the afternoon to perambulate along the streets of famous Bellagio, the Pearl of Lake Como and the site of scenic views and charming houses and storefronts. There are also a number of architectural marvels waiting to be explored, from the Basilica di San Giacomo to the Chiesa di Santa Maria a Loppia. Fine shopping and a quick bite or espresso can be found on the Via Garibaldi, one of the main streets of the town. Your day ends with time spent relaxing along the shores of the lake at the Piazza Mazzini, before getting ready for dinner at the superlative Grill at Villa d’Este this evening.

What's Included: breakfast, flight from Naples to Milan, transfer, lunch, dinner, accommodation

Day 6: An Unforgettable Day on the Lake

Get ready to cruise the dazzling blue waters of Lake Como and visit some of the most darling towns on its shores, as you’ll spend the day on board an elegant boat that will take you to all of the best sights. Make your way past Villa d’Este and arrive in Bellagio, where you’ll be taken to a villa with a spectacular lakeside view, sumptuous wines and sensational hors d’oeuvres. Enjoy lunch in the delightful town of Loppia before setting out on a walking tour of breathtaking Bellagio and the famed English-inspired gardens at the Villa Melzi. The evening sees you back at Villa d’Este, anxious to enjoy another delicious dinner at La Veranda.

What's Included: breakfast, boat tour, walking tour, dinner, accommodation

Day 7: Discovering the Mecca of Italian Fashion

You turn south, heading for the heart of Italy and the pulse of the fashion world: magnificent Milan, home to such world-famous fashion houses as Prada, Versace, Armani and Dolce & Gabbana. You’ll be led through the renowned streets of designers beloved the world over by Simona Iulini, whose effortless sense of style and sharp eye for beautiful goods make her the ideal companion on this adventure in indulgence. 

The afternoon sees you taking in the artistic masterpieces of this unique city, often overlooked for its more famous neighbors, Florence and Venice. Don’t be surprised: You’ll find incredible art in Milan, perhaps even better than what you’ll find in other, more revered Italian cities. Begin by gazing upon the magnificent expanse of fresco known as The Last Supper, one of the crowning achievements of Leonardo da Vinci, recently restored to better reflect the artist’s brilliance. A short walk takes you to the gorgeous courtyards and awe-inspiring skyline of Sforzesco Castle, the current home of Michelangelo’s moving Rondanini Pieta, an inspiring work that is not to be missed. Make your way past the gigantic Gothic façade of the Milan Duomo – one of the largest churches in Europe – before ending your tour of Milan at the incomparable La Scala. Arguably the most famous opera house in the world, there you can learn all about the highest form of Italian musical achievement. The evening sees you back at Villa d’Este.

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

Day 8: Back for More in the Italian Countryside

Your final day by the shores of Lake Como is spent as you please, perhaps a lazy morning with a large and leisurely breakfast before setting out to explore the nearby town of Varenna, an ancient community dating back to the Roman era and formally founded by fisherman in the eighth century. You’ll enjoy a delightful stroll along the promenade that abuts Lake Como, offering sensational views and the fullest enjoyment of the marvelous weather, and you’ll marvel at the Basilica of Saint George, a 14th century structure that was lovingly restored in 1957. 

You can enjoy lunch at a local trattoria before heading to the Villa Monastero, a fascinating edifice that is now a research institution. Your excursion to Varenna ends with a visit to Castello di Vezio, where you’ll get a chance to see an Italian falconer practice his craft with his majestic and magnificent partner. Dinner tonight is at the superb Sant’Anna 1907, where the food is divine and the wine list extensive.

What's Included: breakfast, transfer, dinner, accommodation

Day 9: Venice and the Veneto

Make your way east along the ridge of the mighty Alps towards the welcoming shores of the Adriatic Sea, passing by some of Italy’s best landscapes and through some of her quaintest towns, bound for the canal-riddled metropolis of Venice. While on your way, you’ll stop in Verona, the fictional home of Shakespeare’s most famous lovers and the real-world site for one of the best-kept and oldest Roman amphitheaters in the world. Known as the Verona Arena, the complex is in such good condition, it is still used for performances by the Verona Opera Company. You’ll also want to visit Juliet’s House, the supposed inspiration for Shakespeare’s famous tragedy, the main square of the Piazza delle Erbe, and a viewpoint from which you can gaze upon the stolid Ponte Scaligero, which featured the largest span of any bridge in the known world at the time of its construction.

Continue east until you reach the lagoon and archipelago of romantic Venice, the Queen of the Adriatic and the Floating City, awash in the ochre glow of an Italian sun setting over the lagoon. A private water taxi will deliver you to the hotel while also offering you a first glimpse at this majestic metropolis. Once you reach the hotel, you can drop off your luggage and get ready for a delicious dinner of fresh caught seafood preceded by a freshly-made Bellini cocktail, a true Venetian specialty. From the splendid expanse of the Piazza San Marco to the floating edifice of the church of San Giorgio Maggiore, you’ll be sure to be enchanted by this arresting city.

What's Included: breakfast, transfers, dinner, accommodation

Day 10: Saying Goodbye

This morning, you’ll be taken by private water taxi to the train station, ready to board the train that will take you to the airport for your return flight home. Your head will be swimming with the memories of this amazing expedition, and your heart will be warmed by the thoughts of all the fun you’ve had and all the amazing people you’ve met.

What's Included: breakfast, transfer


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.