Itinerary · Italy
Three weeks in Italy,
north to south
Lake Como to the Amalfi Coast in twenty nights: the lake, Venice, Florence, a medieval borgo in Tuscany, Rome, and six slow nights by the sea.
Three weeks is the Italy trip people talk about for years. It works because it runs one way, top to bottom, and ends by the sea.
Fly into Milan, home from Naples or Rome, and never double back. Every stop is at least two nights and most are three. The coast gets six, split between two hotels, because by the end of three weeks that’s exactly where you’ll want to be.
The moves are written in below exactly as I book them: helicopters where the road is the long way round, a private boat wherever there’s water, and the train only from Venice to Florence, with a meet-and-greet at both ends. Work with me and you get Fora perks at the hotels, typically a space-available upgrade, daily breakfast and a hotel credit, plus someone who knows these hotels personally. Same rate as booking direct.
At a glance
Into Milan, home from Naples. Twenty nights, twenty-one days.
- Lake Como · 3 nights
- Passalacqua, the honeymoon villa above Moltrasio, about an hour from Milan. All my Lake Como hotels.
- Venice · 3 nights
- Airelles Palladio, the most beautiful hotel I have seen in Italy. All my Venice hotels.
- Florence · 2 nights
- Hotel Lungarno, on the river in the Oltrarno, or the Four Seasons. All my Florence hotels.
- Tuscany · 3 nights
- Borgo San Felice, a restored medieval hamlet in the Chianti hills near Siena. Or Il Borro for a honeymoon, or Castello di Casole for a traditional castle. All my Tuscany hotels.
- Rome · 3 nights
- Hotel Eden, the romantic classic above the Spanish Steps, on a quiet street. All my Rome hotels.
- Amalfi Coast · 6 nights
- Hotel Santa Caterina, then Il San Pietro, slow days in Amalfi, then the cliffs outside Positano. Where to stay in Positano.
The twenty-one days
Land in Milan, lunch on the lake
A driver in the arrivals hall at Malpensa with your name on a sign, and about an hour later you’re at Passalacqua. Nothing else on the schedule.
The move: private Mercedes from Malpensa, bags handled from the carousel to your room.
Boats, villas and long lunches
A private boat for a day on the water, with lunch at Silvio, Crotto del Misto or Locanda La Tirlindana. Bellagio from the water, then home somewhere calmer.
The move: a private boat and captain, for as long as you want them.
Over the plain to the lagoon
The longest move of the trip, so it’s the one I’d fly. You land in time for lunch in the garden at Airelles Palladio on Giudecca.
The move: a helicopter to Venice, weather permitting, then a water taxi to the hotel dock. Otherwise a private Mercedes, about three and a half hours.
The city, then the islands
San Marco early with a private guide, before the day-trippers. A private boat out to Murano, Burano and Torcello. The hotel boat reaches St. Mark’s in about five minutes, so the evenings are easy.
The one train leg
The only train of the trip, because it’s faster than any car: a little over two hours, then two nights at Hotel Lungarno in the Oltrarno, two minutes from the Ponte Vecchio.
The move: water taxi to Santa Lucia, met with your name on a sign, porters take your bags to your seat in the top class. Met on the platform in Florence and driven to the hotel.
The Uffizi and the Oltrarno
The Uffizi and the Duomo with a private guide in the morning. A long lunch, then aperitivo on the Oltrarno side, where Florentines actually live.
Into the hills
To Borgo San Felice, a perfectly restored hamlet in the Chianti hills, close to Siena. One of my favorite stays: fantastic service and food, a spa, and it just feels like home. In summer, book dinner in the piazza, when the tables go out in front of the chapel with live music.
The move: a private driver, or a supercar delivered to the hotel in Florence if you’d like to drive yourselves into Chianti.
Wine, hill towns and the spa
One day for Chianti and Siena, one for the Val d’Orcia: Montalcino, Pienza and Montepulciano, with tastings along the way. The borgo’s spa is there to come home to.
The move: a private driver who knows every back road, so nobody chooses between the tasting and the drive home.
South through the Val d’Orcia
Into Rome by the afternoon, and three nights at Hotel Eden, above the Spanish Steps on a quiet street.
The move: a private Mercedes, about three hours, with a lunch stop in the hill towns if you’d like one.
Rome, with a guide and a driver
The Vatican with a private guide at the first entry of the day, the Colosseum and the Forum, and dinner on the rooftop at La Minerva, facing the Pantheon. A driver on call for both days.
Down to the sea
To Hotel Santa Caterina in Amalfi, opened in 1904 and still run by the founding family. The luxury here is quiet and lives in the details.
The move: a helicopter to Scala, close to Ravello, weather permitting. Otherwise a private car to Naples or Salerno and a private boat down the coast, which beats the coast road every time.
Slow days
The pool, the sea, long lunches, and a boat along the coast to Ravello or Capri when you want one thing on the schedule.
The move: private boats, arranged before you arrive.
Along the coast by boat
Three nights at Il San Pietro, on the cliffs just outside Positano: every room has a sea view, nobody can look down on you, and the beach club is on the sunset side.
The move: a private boat from Amalfi, dock to dock.
The sunset side
The beach club, a sunset cruise, dinner in town. The hotel’s own boats and car shuttles run into Positano, so you can be in the middle of it and back on your terrace in minutes.
Out through Naples or Rome
A last breakfast over the sea, then home.
The move: a private car to Naples airport, about an hour and a half, or a helicopter to Rome for a direct flight.
Other versions
- The mountains instead
- Swap Lake Como for the Dolomites. Fly into Venice, start with three nights in the mountains, then carry on south. The mountain hotels I’d pair.
- More Florence
- Three nights in the city instead of two, taken from the countryside. My Florence guide.
- The train as the trip
- La Dolce Vita Orient Express between Rome and Venice on selected departures. Rome, the train and Venice.
- Shorter
- Fourteen days. Rome, Florence, Venice and the lakes or the mountains.
Three weeks in Italy FAQ
Is three weeks too long for one Italy trip?
Not at this pace. No stop is shorter than two nights, most are three, and every move is private and door to door, so the trip never turns into packing and unpacking.
Why travel north to south?
It finishes on the coast, where you’ll want to slow down anyway, and it means one long-haul arrival into Milan and one departure from Naples or Rome, with no backtracking.
Can we swap Lake Como for the Dolomites?
Yes. Fly into Venice instead, spend three nights in the Dolomites first, then come down to Venice and carry on south. My fourteen-day route has the mountain hotels I’d pair.
How do we get from Rome to the Amalfi Coast?
By helicopter to Scala, close to Ravello, if the weather allows. Otherwise a private car to Naples or Salerno and a private boat down the coast to the hotel, which is far more pleasant than the coast road.
When is the best time for three weeks in Italy?
Late spring or early autumn, when the Amalfi Coast hotels are open, the lakes are warm and the cities are calmer than in July and August. Tell me your dates and I’ll tell you honestly how each stop will feel.
Where and when?
“Three weeks in Italy next September, north to south” is a complete answer. I’ll take it from there.