Luxury Italy Tour: Lake Como, Tuscany, & Amalfi

Days 1-3: Lake Como

Fly into Milan, then continue to Lake Como by private helicopter if you choose to upgrade, or by private driver otherwise. You’ll stay at the Mandarin Oriental, a 19th-century villa converted into a five-star lakeside hotel, close enough to the water that most rooms look straight out over it.

Lake Como is a destination best enjoyed at its own pace. Spend your days exploring the villages and villas that line the shoreline, take to the water on a private boat journey, and discover the lake through the eyes of local experts who know its quieter corners. From long lunches overlooking the water to evenings spent at restaurants chosen around your tastes, the itinerary is shaped around how you want to experience Como.

Days 4-7: Tuscany

Helicopter or private driver continues the journey into Tuscany’s hills, where you’ll stay at Villa Ardore, a restored sixteenth-century villa with eight bedrooms set among the vineyards outside Chianti. A private chef runs the kitchen, the cellar is stocked with wine from producers within a short drive, and the heated pool and private spa give the villa its own rhythm separate from whatever the rest of the day has planned.

Day trips reach Siena and San Gimignano’s medieval centers and the vineyards scattered through Chianti’s hills, with a local guide who knows which cellar door is worth knocking on

Days 7-10: Rome

Nowhere else on this trip hits you the way Rome does the moment you step out of the car. Two thousand years of history stacked on top of each other, a Vespa cutting past a column that was already ancient when the Colosseum went up, laundry hanging over a street that Caesar’s army once marched down. Nothing here is staged for you. It’s just still standing, and you happen to be walking through it.

Mornings start at the Colosseum and the Roman Forum with a private guide, and then the afternoon opens up for whatever the city throws at you next: a fitting at a tailor who’s been dressing Roman families for generations, an espresso standing at a bar the way locals actually take it, or simply getting lost in Trastevere until dinner finds you. Evenings run toward Michelin-starred tables, and on the night it’s arranged, an after-hours walk through the Vatican once the crowds have gone and the whole place belongs to you.

You’ll be staying at Hotel Eden, perhaps the most glamorous hotel in town.

Days 10-14: Amalfi Coast

A private driver, or helicopter for anyone who’s upgraded, carries you from Rome to Ravello and Palazzo Avino, a twelfth-century villa turned five-star hotel set a thousand feet above the coastline, with a Michelin-starred restaurant and views over the fishing villages below.

From here, a private boat trip to Capri is the natural next step, or an extended stay on the island itself for anyone who wants more than a day of it. Either way, the coast’s actual pleasures are simple ones done well, limoncello made properly, fresh seafood, and a private boat to a cove nobody else has found that morning.