20-Day Ultimate Italy Luxury Escapes & Epic Journey
Italy is a land where history, art, and the art of living well converge. This 20-day epic journey is designed for the discerning traveler who seeks more than just sightseeing; it is an invitation to immerse yourself in the 'Dolce Vita' through exclusive access, private transfers, and the finest culinary experiences the peninsula has to offer.
From the sun-drenched cliffs of the Amalfi Coast to the aristocratic villas of Lake Como, you will traverse the country using Italy's efficient high-speed rail in Executive Class and private luxury vehicles. This itinerary balances iconic landmarks with hidden gems, ensuring every moment is steeped in comfort and sophistication.
The Itinerary
Day 1: Rome, Italy - The Grand Arrival
Luxury Transfer to Hotel
Arrive at Leonardo da Vinci–Fiumicino Airport and meet your private chauffeur for a seamless transfer to your luxury hotel in the heart of Rome.
Lunch at Piazza Navona
Enjoy a refined welcome lunch overlooking the Fountain of the Four Rivers, sampling traditional Roman pasta dishes.
Private Pantheon Tour
Meet your historian guide for a private walkthrough of the Pantheon, the best-preserved monument of Imperial Rome.
Rooftop Dining
Savor a Michelin-starred dinner with panoramic views of the Eternal City's skyline at a premier rooftop venue.
Day 2: Rome, Italy - Imperial Grandeur
Early Access Colosseum
Beat the crowds with VIP early access to the Arena Floor of the Colosseum, followed by a private tour of the Roman Forum.
Trastevere Gourmet Walk
Explore the charming alleys of Trastevere with a local food expert, tasting artisanal cheeses and premium Roman wines.
Palazzo Doria Pamphilj
Visit this private gallery to see masterpieces by Caravaggio and Velázquez in a lavish, aristocratic setting.
Evening at the Opera
Experience a world-class performance at the Teatro dell'Opera di Roma, the city's premier venue for classical music.
Day 3: Rome, Italy - The Vatican & Beyond
Vatican Museums Private Key-Bearer Tour
Join the 'Clavigero' (Key Bearer) to open the doors of the Vatican Museums and Sistine Chapel before the public arrives.
St. Peter's Basilica VIP Entry
Explore the world's largest church with a private guide, including a visit to the dome for breathtaking views.
Borghese Gallery
Admire Bernini’s sculptures and Titian’s paintings in this exclusive gallery located within Rome’s most beautiful park.
Wine Tasting in a Secret Cellar
Descend into a historic cellar for a curated tasting of rare Italian vintages led by a master sommelier.
Day 4: Florence, Italy - To the Cradle of the Renaissance
Frecciarossa Executive Class to Florence
Travel from Rome Termini to Florence Santa Maria Novella in the ultra-luxury Executive Class carriage.
Arrival & Florentine Steak Lunch
Check into your hotel and enjoy a traditional Bistecca alla Fiorentina at a historic local trattoria.
Duomo Complex Tour
Visit the Cathedral of Santa Maria del Fiore and the Baptistery with exclusive access to the hidden terraces.
Oltrarno Artisan Workshops
Cross the Ponte Vecchio to visit private ateliers where masters practice leatherwork and gold-smithing.
Day 5: Florence, Italy - Artistic Masterpieces
The Uffizi Gallery Private Tour
Spend the morning with an art historian discovering the works of Botticelli, Michelangelo, and Leonardo da Vinci.
Gourmet Lunch at Mercato Centrale
Dine at the upper level of the historic market, featuring artisanal dishes from across Tuscany.
Accademia Gallery
View Michelangelo’s 'David' with a private guide who will explain the sculpture's profound historical significance.
Sunset at Piazzale Michelangelo
End the day with a private chauffeur-driven trip to the best viewpoint in Florence for a sunset aperitivo.
Day 6: Florence, Italy - Villas and Gardens
Boboli Gardens & Pitti Palace
Explore the vast Medici gardens and the Palatine Gallery, housing an impressive collection of Renaissance art.
Lunch in Fiesole
Drive to the hilltop town of Fiesole for lunch at a luxury villa overlooking the entire Arno Valley.
Luxury Leather Workshop
Participate in a private workshop at a prestigious leather school to create your own bespoke Italian accessory.
Chef's Table Experience
Enjoy an intimate 8-course tasting menu at a Michelin-starred restaurant in the heart of Florence.
Day 7: Tuscany, Italy - The Chianti Wine Route
Private Driver to Chianti Classico
Leave the city for a scenic drive through the rolling hills and cypress-lined roads of the Chianti region.
Castello di Ama Vineyard Tour
Visit this renowned estate for a private tour of their contemporary art collection and premium wine tasting.
Al Fresco Lunch in Greve
Dine on local specialties in the charming square of Greve in Chianti, accompanied by estate-grown olive oils.
San Gimignano Visit
Explore the 'Manhattan of the Middle Ages,' famous for its medieval towers and world-class gelato.
Day 8: Tuscany, Italy - Val d'Orcia Perfection
Siena Private Walking Tour
Discover the Piazza del Campo and the stunning Duomo di Siena with a guide who specializes in the Palio history.
Montalcino Brunello Experience
Enjoy a private tasting of Brunello di Montalcino, one of Italy’s most prestigious red wines, at a hilltop fortress.
Pienza Cheese Tasting
Visit the 'Ideal City' of Pienza to sample authentic Pecorino cheese directly from local producers.
Tuscan Farmhouse Dinner
Relax with a farm-to-table dinner featuring seasonal truffles and handmade pasta in a rustic luxury setting.
Day 9: Venice, Italy - The Floating City
Luxury Transfer to Venice
Travel by private car to Florence station and board the high-speed train to Venice Santa Lucia.
Private Water Taxi Arrival
Arrive in style as a private mahogany water taxi whisks you through the Grand Canal to your hotel's private dock.
St. Mark's Square & Basilica
Explore the golden mosaics of St. Mark's with a private guide, including access to the Pala d'Oro.
Cicchetti & Wine Tour
Join a local connoisseur for a tour of Venice's hidden 'Bacari' bars to enjoy traditional Venetian appetizers.
Day 10: Venice, Italy - Doges and Gondolas
Secret Itineraries of the Doge's Palace
Gain access to the restricted areas of the palace, including the torture chambers and the Bridge of Sighs.
Seafood Lunch at Rialto
Dine on fresh catches from the lagoon at a prestigious restaurant near the historic Rialto Market.
Private Luxury Gondola Ride
Experience the canals away from the tourist routes in a meticulously maintained, private gondola.
Dinner at Harry's Bar
Visit the legendary birthplace of the Bellini cocktail for a classic Venetian dinner steeped in history.
Day 11: Venice, Italy - Lagoon Islands
Private Bragozzo Boat Tour
Board a traditional Venetian wooden boat for a private excursion to the islands of Murano, Burano, and Torcello.
Murano Glass Masterclass
Watch a private glass-blowing demonstration by a master artisan and visit their exclusive showroom.
Lunch on Burano
Enjoy a leisurely lunch of 'Risotto di Gò' on the colorful island of Burano at a world-famous local trattoria.
Torcello Cathedral
Visit the oldest church in the lagoon to see the stunning Byzantine mosaics in a peaceful, rural setting.
Day 12: Lake Como, Italy - Alpine Elegance
First Class Train to Milan
Depart Venice for Milan, then continue by private luxury transfer to the shores of Lake Como.
Lakeside Lunch in Como Town
Dine at a premier restaurant overlooking the water before checking into your lakeside grand hotel.
Funicular to Brunate
Take the historic funicular up to the village of Brunate for spectacular views of the lake and the Alps.
Gala Dinner
Enjoy a sophisticated evening of fine dining within the frescoed halls of your historic villa hotel.
Day 13: Lake Como, Italy - Villas of the Stars
Private Riva Boat Tour
Spend the morning on a classic mahogany Riva boat, cruising past the glamorous villas of George Clooney and others.
Villa del Balbianello
Dock at the most beautiful villa on the lake for a private tour of its gardens and museum.
Lunch on Isola Comacina
Experience the legendary fixed-menu lunch at the only island on Lake Como, a favorite of celebrities for decades.
Lenno Waterfront Walk
Stroll through the picturesque village of Lenno and enjoy a premium gelato by the lake.
Day 14: Lake Como, Italy - Bellagio & Varenna
Exploring Bellagio
Wander through the 'Pearl of the Lake,' exploring boutique silk shops and the gardens of Villa Melzi.
Gourmet Picnic in Varenna
A private boat will take you to a secluded spot near Varenna for a luxury picnic prepared by a private chef.
Villa Monastero
Visit this former monastery in Varenna, renowned for its long botanical garden stretching along the lakefront.
Farewell Lake Dinner
Dine at a Michelin-recommended restaurant in Torno, featuring fresh lake fish and local white wines.
Day 15: Milan, Italy - High Fashion & History
Private Transfer to Milan
A luxury sedan will drive you from Lake Como to the fashion capital of Italy.
Duomo Rooftop VIP Access
Take the elevator to the terraces of the Milan Cathedral to walk among the spires and statues.
Quadrilatero della Moda Shopping
Enjoy a private shopping experience with a personal stylist in the world's most famous fashion district.
Teatro alla Scala
Attend an opera or ballet at La Scala, followed by a late-night dinner at the nearby Savini in the Galleria.
Day 16: Amalfi Coast, Italy - Southern Splendor
Flight to Naples & Private Transfer
Fly from Milan Linate to Naples, followed by a private chauffeur drive along the winding Amalfi Coast road.
Arrival in Positano
Check into your cliffside hotel and enjoy a lunch of Scialatielli pasta with fresh seafood overlooking the sea.
Positano Boutique Exploration
Walk through the vertical town, visiting high-end boutiques for bespoke linen clothing and handmade sandals.
Candlelit Dinner
Dine at a world-famous cliffside restaurant where the tables are perched directly over the Mediterranean.
Day 17: Amalfi Coast, Italy - The Isle of Capri
Private Yacht Charter to Capri
Spend the day on a private luxury yacht, circumnavigating the island of Capri and visiting the Faraglioni rocks.
Blue Grotto Private Access
Experience the ethereal blue light of the grotto from a small rowing boat before the main tourist boats arrive.
Lunch at La Fontelina
Dine at the most exclusive beach club on Capri, accessible only by boat or a steep coastal path.
Anacapri & Chairlift
Take the chairlift to the summit of Monte Solaro for the highest and best views of the entire Gulf of Naples.
Day 18: Amalfi Coast, Italy - Ravello Heights
Transfer to Ravello
Travel up the mountainside to the peaceful village of Ravello, known as the 'City of Music.'
Villa Cimbrone Gardens
Walk to the 'Terrace of Infinity' for a view so spectacular it was once described as the most beautiful in the world.
Cooking Class in a Lemon Grove
Participate in a private culinary lesson focusing on Amalfi lemons and traditional coastal recipes.
Ravello Festival Concert
If visiting in summer, enjoy an outdoor classical concert held on a stage suspended over the sea.
Day 19: Amalfi Coast, Italy - Pompeii & Vesuvius
Pompeii Archaeologist-Led Tour
Take a private transfer to Pompeii for an in-depth tour of the excavations led by a professional archaeologist.
Wine Tasting on Mt. Vesuvius
Visit a vineyard on the slopes of the volcano to taste 'Lacryma Christi' wine and enjoy a rustic Neapolitan lunch.
Herculaneum Visit
Explore the smaller, better-preserved neighbor of Pompeii, which offers an intimate look at Roman domestic life.
Final Amalfi Sunset Dinner
Celebrate your penultimate night with a grand seafood feast at a Michelin-starred restaurant in Amalfi town.
Day 20: Rome, Italy - The Final Farewell
High-Speed Train back to Rome
Transfer to Salerno or Naples and take the Frecciarossa back to Rome for your final day.
Last Minute Shopping at Via Condotti
Visit the flagship stores of Gucci, Prada, and Valentino for any final luxury acquisitions.
Tiber River Private Cruise
Enjoy a relaxing private boat ride on the Tiber, seeing the city from a different perspective with a glass of prosecco.
Final Michelin Dinner
Conclude your 20-day journey at La Pergola, Rome's only three-star Michelin restaurant, for a night to remember.
Best Time to Visit Italy
The ideal time to embark on this luxury journey is during the shoulder seasons of late spring (May to June) and early autumn (September to October). During these periods, the weather is pleasantly warm, the landscapes are lush or golden, and the extreme crowds of July and August are avoided. Spring is particularly beautiful for the gardens of Lake Como and Tuscany, while September offers the best sea temperatures for the Amalfi Coast and the vibrant harvest atmosphere in the vineyards.
Currency & Money
Italy uses the Euro (€). Credit cards are universally accepted in hotels, high-end restaurants, and luxury boutiques. However, it is advisable to carry some cash for smaller purchases in local markets or for tipping. Tipping is not mandatory but is highly appreciated for exceptional service in luxury establishments; usually, a 5-10% tip or rounding up the bill is appropriate. Contactless payment is standard across the country.
Getting Around Italy
For intercity travel, the Frecciarossa and Italo high-speed trains are the gold standard, offering Executive and Club classes with meal service and lounge access. For the Amalfi Coast and Lake Como, private chauffeur services are recommended due to the narrow, winding roads. Within cities like Venice, private water taxis are the most efficient and luxurious way to navigate. Domestic flights are useful for long distances, such as moving from the north (Milan/Venice) to the south (Naples/Sicily).
