GRAND ITALIAN ODYSSEY

ITALY

Rome has been absorbing visitors for two thousand years and has yet to run out of things to show them. This journey starts there, moves through Tuscany's vineyard-covered hills and medieval hill towns, and ends on the Amalfi Coast, where the road winds above cliffs that drop straight to the water. Fourteen nights. Italy at full length, with enough time in each place to actually arrive.

Note that everything you see here is an example of what your trip could look like. Your adventure will be tailored specifically to you.

WHEN TO GO

DURATION

APR - OCT

14 NIGHTS

LANGUAGE

ITALIAN

CURRENCY

EURO

ESTIMATED COST

$22,800

per person, excl. int'l flights

(based on two adults sharing)

Why this adventure

Italy rewards people who resist the urge to cover everything. The traveler who spends three days in a single Roman neighborhood learns more than the one who hits eight cities in two weeks, and comes back with better stories. This journey is built around that premise: private access to artistic treasures that most visitors queue for hours to glimpse, meals that begin with what's growing within walking distance, and lodges in Tuscany where the view from the window hasn't changed much in five centuries. Each chapter, Rome, Tuscany, the Amalfi Coast, has its own rhythm and its own particular way of getting under your skin. We designed the itinerary to give each one the time it deserves.

Journey flow

Rome opens the journey with the weight of two millennia behind it. The Forum, the Pantheon, the Vatican, and the neighborhoods that most tourists walk through without stopping long enough to understand any of them. Tuscany follows: the road south into rolling hills and cypress lines, the slower rhythms of wine country, and the medieval towns that sit on their ridges as though they've been there forever, which they more or less have. The Amalfi Coast closes the journey with cliffs, sea, and the particular Italian genius for making a landscape look like it was arranged specifically for the pleasure of people sitting on terraces with a glass of something cold.

Take it farther

An after-hours visit to the Vatican Museums or the Borghese Gallery, arranged through the right connections, changes what those spaces feel like entirely. The truffle season in Tuscany peaks in autumn, and a morning in the woods with a local tartufaio and his dogs, followed by lunch at the estate, is one of those experiences that doesn't translate well into a photograph but travels home with you anyway. Capri is an hour by boat from the Amalfi Coast and worth at least a day, preferably more.

Customize this itinerary

Every trip we design is built around you: your pace, your curiosity, your definition of a good day. No set departures, no group tours, no one-size-fits-all anything. If this itinerary sparks something in you, let's talk about what that could look like for you specifically.

START YOUR JOURNEY

Adventure highlights

CULINARY ITALY

Rome's historic trattorias, Tuscan estate kitchens, and Amalfi Coast seafood: the food changes completely with each region, and the thread connecting them is the Italian conviction that eating well is not an indulgence but a form of basic dignity. Private cooking experiences and market visits with local chefs make this explicit.

AMALFI COAST BY BOAT

The Amalfi Coast's most interesting geography is below the road. Private boat excursions cover the sea caves, hidden grottos, and cliffside villages that the winding SS163 can't reach. The Grotta dello Smeraldo, where the water turns an improbable green from light refracting through underwater openings, is worth the detour.

TUSCAN ESTATE LIVING

A working organic estate in the Val di Merse where the food comes from the same ground you're walking on, the wine comes from the vines outside the window, and the medieval hill towns of Siena, San Gimignano, and the Crete Senesi are close enough for a morning drive.

ROME: THE PRIVATE VERSION

The Colosseum at dawn before the crowds arrive, the Vatican Museums with a guide who knows which rooms to skip and which to spend an hour in, and the neighborhoods that don't appear on most itineraries but stay with you longer than the monuments do.

How it unfolds

DAYS 1-5

ROME

Five days in Rome is barely enough and considerably more than most people give it. The Colosseum, the Forum, the Palatine Hill, the Vatican Museums, the Sistine Chapel: the standard circuit earns its reputation and a private guide makes it considerably less exhausting. But the better Rome is the one between the monuments: the Trastevere neighborhood in the early morning before it fills up, the Campo de' Fiori market, the aperitivo hour that begins around six and doesn't rush.

DAYS 6-9

TUSCANY

The road north from Rome arrives in Tuscany with a change in pace that is almost physical. The Val di Merse sits 40 minutes south of Siena in the quieter, less-visited part of the region, and the days here take on the rhythm of the land: vineyard walks, wine tastings, and farm-to-table dinners at estates where the ingredients came from the same ground you walked on that morning. Day trips reach Siena, San Gimignano, and the roofless nave of the Abbey of San Galgano, where the sky takes the place of the ceiling and the effect is more affecting than most intact cathedrals.

DAYS 10-14

AMALFI COAST

The coast delivers exactly what it promises and then some. Private boat excursions reach the sea caves and hidden coves that the coastal road misses. Positano from the water looks like a film set. Ravello, 365 meters above the sea, looks like it was placed there specifically to make everything below it look small. Five nights is enough to cover the coast's range without turning it into a tour.

Where you could stay

HOTEL DE RUSSIE

Built in 1818 on Via del Babuino between Piazza del Popolo and the Spanish Steps, with a discreet façade that conceals a 0.7-acre garden designed by Giuseppe Valadier, full of palm trees, citrus plants, climbing roses, and the occasional glimpse of ancient ruins. Two Michelin Keys, 122 rooms, and a cocktail bar, the Stravinskij, where the list of former regulars includes Picasso, Stravinsky, and Fellini. Le Jardin de Russie serves under the garden's canopy when the weather cooperates, which in Rome between May and September is most of the time. The kind of hotel that has been doing this long enough to make it look effortless.

BORGO SANTO PIETRO

A 300-acre organically cultivated estate in the Val di Merse region of Tuscany, 40 minutes south of Siena, where medieval pilgrims once stopped to heal and rest. Twenty-two individually styled rooms and suites in a 13th-century villa, a Michelin-starred restaurant, holistic spa, organic skincare range Seed to Skin, and a working farm whose output appears on the table each evening. A Michelin-starred treehouse restaurant built around a magnificent oak, and a spa team that takes biodynamic cultivation as seriously as the kitchen does. The kind of Tuscan property that makes leaving feel like a minor tragedy.

HOTEL CARUSO

An 11th-century palazzo perched 365 meters above Ravello, with 50 rooms, frescoed salons, terraced gardens, and an infinity pool at the cliff's edge that the hotel describes as suspended between sea and sky, which for once is not an exaggeration. The Belvedere Restaurant serves Campanian cuisine with views that make concentration difficult. The hotel's traditional wooden boat, Ercole, runs a complimentary daily tour along the coast for guests, which is a reasonable argument for spending at least one afternoon on the water. Jackie Kennedy stayed here. The view hasn't changed.

Ready to start planning?

All Peregrine trips include:

Every trip we design starts from scratch, built around how you travel and what you're actually after. No fixed routes, no shared departures, no compromises. If something on this page resonated, that's a good place to start a conversation.