Luxury Custom Italy Vacations
Time, space and the right people around you. Custom Italy vacations designed from a blank page by Italian-born planners, with drivers, guides and boats reserved for your party alone.
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Quiet Confidence, Arranged in Advance
The Vatican Museums before the crowds. A table on a Ravello terrace held for the hour the light changes. A winemaker in the Langhe who pours the Barolo he made himself. Luxury in Italy is rarely a thing you can point at. It is the absence of waiting, the right person at the door, and the sense that someone thought of it first.
Every luxury Italy vacation we design starts from a conversation about how you like to travel. Then we choose the hotel style for each stop, reserve the drivers, guides and boats for your party alone, and arrange the days in the order that makes sense. Before you leave, a briefing call and a printed trip book. While you are there, a line in Italy answers day and night.
Begin with a conversation, not a catalog.
Tell us how you like to travel. A planner calls within one business day.
Designed from what you tell us. No catalog, no fixed departures.
Private drivers, guides and boats. Nobody joins.
The style first, then the property, held once we know your dates.
A line in Italy from the arrivals hall to the flight home.
Villas and Estates in Tuscany and Umbria
A countryside estate above the Val d’Orcia, with a pool, olive groves and Montalcino on the next ridge. Private tastings of Brunello di Montalcino and Vino Nobile di Montepulciano in family cellars. A cooking class with what came from the market that morning.
From there, Florence is an easy drive for the Uffizi, and Umbria’s hill towns, Assisi, Todi and Orvieto, are a day away. Best for travelers who want to unpack once and stay a week.
The Amalfi Coast and Capri by Private Boat
The coast road is beautiful and famously slow, so we move you by water. A full day on a private boat from Positano to Amalfi, a swim in a cove below the cliffs, lunch on Capri and the Gardens of Augustus in the afternoon light.
Evenings belong to Ravello, high above the Gulf of Salerno, when the day visitors have gone home. Best for couples and families who want the sea at the center of the trip.
Lake Como and the Villas of the North
A private boat linking Bellagio, Varenna and the villa gardens along the shore. Isola Bella’s terraced Baroque garden on Lake Maggiore. In Rome and Florence, Villa Lante’s water theater, Villa Farnese at Caprarola and Villa Gamberaia above the Arno Valley.
Best for travelers who measure a trip in gardens, frescoes and the view from a loggia.
Piedmont, Chianti and the Great Tables
In the Langhe, the person who made the Barolo usually pours it, and lunch arrives with tajarin and the estate’s own Dolcetto. Come in October and the white truffle market in Alba is open on Saturday morning. In Chianti, the castle road links fortified estates and family cellars.
We reserve the tastings and the tables, and arrange a driver so nobody has to think about the drive home.
Sample Luxury Adventures to Start From
Open one and choose the five-star or villa hotel style at each stop. Then send it to a planner.
Best for travelers who seek rare garden access and Renaissance villas
The Vatican Gardens, Villa Lante’s water theater, Villa Farnese and Villa Gamberaia above Florence.
Best for ancient ruins, coastal scenery and island escape
Pompeii with a private guide, the Raphael Rooms, Positano and the Gardens of Augustus.
Best for wine lovers and hill town explorers seeking quiet Umbria and rural Tuscany
Umbria’s quiet hill towns from a base near Bettona, then the Siena countryside, with wine at every turn.
Best for wine lovers seeking Barolo and white truffle country
Barolo Castle, Alba in truffle season, Monforte and Serralunga d’Alba and the Pollenzo wine bank.
Best for families seeking culture, history and artisan traditions beyond Venice
Udine’s arcades, San Daniele prosciutto, Habsburg Trieste, Miramare and Murano glass.
Best for wine lovers seeking Tuscany’s great estates and medieval hill towns
Chianti Classico, Brunello and Vino Nobile tastings, Siena’s Campo and a villa cooking class.
Open an Adventure. Make It Yours.
Every sample adventure on this site is a working plan, not a brochure. Open one and shape it the way you would with a planner across the desk. Nothing is booked and nothing is charged. When you send it, an Italian-born planner calls to talk it through.
Change the nights
Add a night in Florence, take one from Venice. Every stop has its own plus and minus.
Choose the hotel style
A five-star in the historic center, a countryside estate, or an apartment for three generations. We name the property once we know your dates.
Add what you love
Food tours, a private boat day, a cooking class, the Vatican before the crowds. Interests are matched to each city.
Save it, then send it
Save the adventure to My Adventures, come back to it later, and send it to a planner when it feels right.
How a Luxury Trip Comes Together
A conversation first
How you like to travel, what you have seen, what the trip is for. The trip designer takes three minutes, or call us.
A first draft
Route, nights, hotel style and the days we arrange, usually within a day or two.
Refined with you
We adjust until it reads like your trip. Then we name the hotels and hold the rooms.
Looked after throughout
Briefing call, printed trip book, private transfers and a line in Italy, day and night.
Start With a Conversation
Three quick answers and your details. An Italian-born planner calls you within one business day to listen first, then sketch the trip. Prefer the phone? We are in Houston, on Central time.
Custom adventures begin at $8,500 per person, land only.
Talk to a Trip Planner
Three quick answers and your details.
Luxury Italy Vacation Questions
Luxury here is time, space and the right people around you. Every trip is custom, designed from what you tell us rather than chosen from a catalog. Drivers, guides and boats are reserved for your party alone. Hotels are selected for how you travel, from a five-star in the historic center to a countryside estate. A planner who grew up in Italy designs it, and a line in Italy answers day and night while you travel.
We choose the hotel style with you first: a grand hotel near the Spanish Steps, a palazzo on the Grand Canal, a villa in the Chianti hills, a lake house with a garden. Once we know your dates and preferences, your planner names the properties that fit and holds the rooms. Availability in high season moves quickly, which is one reason to start early.
Yes, and they are the backbone of most trips we plan. A private driver between cities, so nobody manages luggage on a train. A guide for your party alone at the Vatican, the Uffizi or Pompeii. A private boat for a full day on the Amalfi Coast or Lake Como. Each is reserved for your group and nobody else joins.
Yes. Open any sample adventure in the adventure builder, choose the five-star or villa hotel style at each stop, add the interests you want, and send it to a planner. We take it from there and refine the details with you.
For the Amalfi Coast, Lake Como, Venice and Tuscany between May and September, six to nine months gives the best choice of rooms and the best times for timed entries. Spring and autumn trips can be planned four to six months out. We also arrange shorter-notice trips whenever the right rooms are available.
Yes, all twenty regions. Most luxury travelers start with Rome, Florence, Venice, the Amalfi Coast or Lake Como, and many return for Piedmont in truffle season, Puglia, Sicily, the Dolomites or Friuli Venezia Giulia.
Your Italy, arranged in advance.
No obligation. Italian-born planners, since 2003.