Nine days, three Italys. Begin in Rome, where the city exhales after summer and its palazzi glow in the low light. Drive south through the Val d’Orcia as the Brunello harvest begins, then finish on the Amalfi Coast while the sea is still warm and the crowds have gone home. This is our favourite way to see Italy in September: slow, private and entirely your own.
Journey of the Month · September 2026
Italy La Dolce Vita Beyond the Ordinary
Italy in September reveals its most elegant side: golden vineyards, fewer crowds, exceptional gastronomy and perfect weather for private journeys.
Plan this journeySeptember 2026
Why this destination now?
Italy in September reveals its most elegant side: golden vineyards, fewer crowds, exceptional gastronomy and perfect weather for private journeys.
The heat of August has softened, the sea is at its warmest and the countryside is busy with the vendemmia, the grape harvest. Restaurants that were impossible to book in July have tables again, and the light, low and gold, makes every view look like a painting.
- Weather
- 24–29°C, long sunny days
- Sea
- Around 24°C on the Amalfi Coast
- Season
- Grape harvest & first truffles
- Ideal length
- 9 to 12 nights
The route
Your journey, stage by stage
Our suggested route moves at an unhurried pace, with private transfers throughout. Every stage can be lengthened, shortened or swapped.
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Days 1–3
Rome, after hours
Arrive by private transfer to a suite above the Spanish Steps. Explore the Vatican Museums after the doors have closed to the public, wander Trastevere with a food historian and end each evening on a rooftop as the domes turn pink.
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Days 4–6
Val d’Orcia & Montalcino
Drive north through the cypress-lined roads of southern Tuscany. Join the harvest at a Brunello estate, hunt for truffles with a local tartufaio and taste in cellars that are rarely opened to visitors. Evenings belong to long dinners under the vines.
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Days 7–9
The Amalfi Coast
Continue south to Positano by private car. Spend a day at sea aboard a classic wooden boat to Capri, swim in coves that can only be reached by water and toast your last night on a candlelit terrace above the Tyrrhenian Sea.
Places we love
Where to stay
Hotel
Hotel de la Ville
Rome
Rocco Forte’s palazzo at the top of the Spanish Steps, with a rooftop bar that looks across the whole of the Eternal City.
Estate
Rosewood Castiglion del Bosco
Montalcino, Tuscany
A medieval estate of vineyards and villas in the heart of Brunello country: perfect timing for the harvest.
Villa
A private villa in the Val d’Orcia
Southern Tuscany
For families and friends: a restored farmhouse with pool, private chef and nothing but cypress trees on the horizon.
Hotel
Il San Pietro di Positano
Positano, Amalfi Coast
Carved into the cliff with a lift down to its own beach. Few hotels in Italy feel this personal.
At the table
Dining & gastronomy
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La Pergola
Three Michelin starsRome
Heinz Beck’s celebrated dining room, with a view over the whole of Rome. Book the window table, and the wine cellar tour.
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Roscioli Salumeria con Cucina
Roman institutionRome
The carbonara every Roman argues about. Ask us to reserve the cellar room for a private tasting.
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Dopolavoro La Foce
Estate diningVal d’Orcia, Tuscany
Simple, perfect Tuscan cooking in a former workers’ club, looking out over the famous zig-zag road of cypresses.
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La Sponda at Le Sirenuse
Michelin-starredPositano
Dinner by the light of hundreds of candles, with the village falling away to the sea below.
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Da Adolfo
Arrive by boatPositano
Look for the red fish on the boat’s mast. Grilled mozzarella on lemon leaves and white wine with peaches, toes in the sand.
Only with us
Exclusive experiences
The Sistine Chapel, after hours
A private visit to the Vatican Museums once the crowds have gone, ending in near-silence beneath Michelangelo’s ceiling.
Harvest day at a Brunello estate
Pick grapes with the winemaker, then lunch among the vines and taste vintages straight from the barrel.
A classic boat to Capri
A day at sea aboard a wooden Riva-style boat: the Faraglioni, hidden grottoes and lunch at a beach club only reachable by water.
From our specialists
Insider tips
- Reserve after-hours Vatican access at least six weeks ahead. Private slots in September are limited and sell out first.
- The harvest usually starts in mid to late September. We confirm the exact dates with the estate a few weeks before you travel.
- On the Amalfi Coast, travel by boat rather than road whenever you can. It is faster, cooler and far more beautiful.
- Pack a light layer for the evenings in Tuscany: hill towns cool down quickly after sunset, even in early autumn.
- Churches in Rome require covered shoulders and knees. A silk scarf in your bag solves it in seconds.
Make this journey yours
Every element can be shaped around you: dates, pace, hotels and the moments that matter most.
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