La Dolce Vita
Venice to Amalfi: Art, Food & Endless Beauty
Italy doesn't just welcome visitors—it seduces them. From the impossible beauty of Venice's canals to the sun-drenched terraces of the Amalfi Coast, this journey is an immersion in la dolce vita: the sweet life. You'll hunt truffles in Tuscany, make pasta with a nonna, sip Barolo in ancient cellars, and discover why Italy has captivated travelers for centuries.
This itinerary is a starting point. Every element can be adjusted—add days, change hotels, swap experiences, alter the pace. We'll craft the final journey around your preferences, travel dates, and dreams.
Your Journey Unfolds
Arrival in Venice
Arrive at Marco Polo Airport and transfer by private water taxi through the lagoon. Your first glimpse of Venice from the water is unforgettable—a city that seems to float on dreams.
Venice was built on 118 small islands, connected by 400 bridges, with no roads—only canals. It shouldn't exist, and yet it has thrived for 1,500 years. Every stone here defies logic and gravity.
Stay: Aman Venice or Gritti Palace
Venice: Art & Secrets
Private guided tour of the Doge's Palace and St. Mark's Basilica before the crowds. Afternoon exploring hidden Venice—artisan workshops, cicchetti bars, and squares where tourists never venture.
Venice was once the world's richest city, ruling a maritime empire from the Adriatic to Constantinople. The Doge's Palace held secrets, prisons, and the machinations of power. Behind its beauty lies a history of cunning and conquest.
Stay: Aman Venice or Gritti Palace
Venice: Lagoon & Islands
A day on the lagoon. Visit Burano with its rainbow houses, Torcello with its ancient cathedral, and hidden islands where monks still make wine. Return to Venice for a Bellini at Harry's Bar.
Burano's houses are painted bright colors so fishermen could find their way home through the fog. Each color was assigned by the government—you couldn't just paint your house pink. Even beauty, in Venice, was regulated.
Stay: Aman Venice or Gritti Palace
Venice to Tuscany
Private transfer through the Veneto and into Tuscany. Stop in Bologna for the world's best tortellini in brodo, then continue to your villa in the Chianti hills.
Bologna is called "La Grassa" (The Fat One) for its legendary cuisine. Tortellini were supposedly modeled on Venus's navel—a local innkeeper glimpsed her through a keyhole. Whether the story is true, the pasta is divine.
Stay: Castello di Casole or Rosewood Castiglion del Bosco
Truffle Hunting in Tuscany
Morning truffle hunt with a local trufolao and his dogs. The forest floor holds buried treasure—white or black, depending on season. Lunch features your finds, prepared simply to let the truffle sing.
Truffle hunters guard their spots with fierce secrecy—some families have hunted the same woods for generations. The dogs (never pigs anymore, too greedy) are treated like royalty. A good truffle dog is worth more than a car.
Stay: Castello di Casole or Rosewood Castiglion del Bosco
Siena & San Gimignano
Visit Siena, frozen in medieval amber, and San Gimignano with its forest of towers. Taste Brunello di Montalcino in its birthplace. Return to your villa for dinner under the stars.
San Gimignano once had 72 towers—medieval skyscrapers built by rival families to show their power. Only 14 remain, but they still bristle against the sky like a stone forest. Tuscany's history is written in architecture.
Stay: Castello di Casole or Rosewood Castiglion del Bosco
Florence: Renaissance Glory
Drive to Florence for two nights of Renaissance immersion. Private after-hours tour of the Uffizi—Botticelli's Venus, Michelangelo's Tondo Doni—without the crowds.
The Medici family collected art like others collected coins. They funded Botticelli, Michelangelo, Leonardo. Without their patronage, the Renaissance might never have happened. Florence exists because one family believed beauty was worth everything.
Stay: Four Seasons Florence or Portrait Firenze
Florence: Artisans & Aperitivo
Morning visiting artisan workshops in the Oltrarno—leather craftsmen, paper marbling, goldsmithing. Afternoon: the Accademia to see Michelangelo's David. Evening: aperitivo overlooking the Ponte Vecchio.
Michelangelo carved David from a block of marble that two other sculptors had already rejected. They said the stone was flawed. Michelangelo saw a giant hiding inside, waiting to be freed. Genius sees what others miss.
Stay: Four Seasons Florence or Portrait Firenze
Florence to Rome
High-speed train to Rome—Italy's eternal city. Afternoon exploring Trastevere, the neighborhood that feels most like a village. Dinner at a trattoria where the menu hasn't changed in decades.
Rome wasn't built in a day, and you can't see it in a day either. Layers of history pile atop each other here: a Renaissance church built on a medieval house built on Roman ruins. Every corner holds 3,000 years.
Stay: Hotel de Russie or Rocco Forte House
Rome: Ancient & Baroque
Morning at the Colosseum and Roman Forum with an archaeologist guide. Afternoon: the Vatican Museums and Sistine Chapel. Evening: gelato and a stroll through Piazza Navona.
The Colosseum could hold 50,000 spectators—more than most modern stadiums. It had a retractable awning, numbered seats, and trap doors for wild animals. The Romans invented mass entertainment, for better and worse.
Stay: Hotel de Russie or Rocco Forte House
Rome to Amalfi Coast
Drive south through the Campanian countryside to the Amalfi Coast. As the road winds above sheer cliffs, the views become increasingly impossible. Arrive in Ravello, perched 1,000 feet above the sea.
Ravello has been called "closer to the sky than the sea." Wagner composed here, Greta Garbo hid here, Gore Vidal lived here for decades. It's a place where beauty reaches a pitch that demands creativity.
Stay: Belmond Hotel Caruso or Palazzo Avino
Amalfi & Positano
Explore the coast by private boat. Stop in Positano to wander candy-colored streets, in Amalfi to see the cathedral, at hidden coves for swimming. Return for sunset cocktails on your terrace.
Positano was a poor fishing village until writers and artists discovered it in the 1950s. John Steinbeck wrote: "Positano bites deep. It is a dream place that isn't quite real when you are there and becomes beckoningly real after you have gone."
Stay: Belmond Hotel Caruso or Palazzo Avino
Pompeii & Cooking Class
Morning excursion to Pompeii—a Roman city frozen in volcanic ash. Return for a cooking class at a family farm: making limoncello, hand-rolling gnocchi, learning secrets passed down for generations.
When Vesuvius erupted in 79 AD, it buried Pompeii in 20 feet of ash. When excavators uncovered it centuries later, they found bread still in ovens, wine still in cups. It's not ruins—it's a city paused mid-breath.
Stay: Belmond Hotel Caruso or Palazzo Avino
Departure
A leisurely morning before transfer to Naples airport. Perhaps a final espresso, a last glimpse of the sea. Italy doesn't say goodbye—it says "arrivederci": until we see each other again.
The Italians have a concept called "la bella figura"—making a beautiful impression. It's not just about appearance; it's about living beautifully, savoring every moment. After two weeks here, you understand: this isn't a vacation philosophy. It's a life philosophy.
Stay: Day use available
Ready to Begin?
This journey is waiting to be shaped around you. Tell us your dates, your preferences, your dreams—and we'll craft something extraordinary.