September · October · November · Christmas

Italy's Most Delicious Season

Vendemmia, truffles, olive harvest and Christmas

Explore the Season Create a Private Journey

25 years of private journeys Local hosts across Italy Private drivers · 24h assistance Featured in National Geographic Traveller UK

There is a moment each September when Italy exhales. This is the season the Italians keep for themselves.

Autumn is when the country becomes intensely local again. The heat softens. Tables get longer. Wine cellars are alive, olive mills are working and small towns celebrate what they have grown, cooked and made for generations.

Journeys of the season

5 curated journeys · September - December 2026

I September – December · 8 days

Flavors of Fall in Tuscany

Olive Harvest • Truffles • Wine • Cooking

This is the season the estate was made for. You arrive as the olives come off the trees and the first oil of the year is pressed, still green and peppery. The week moves with the harvest: a morning truffle hunt with the dogs, garden-to-kitchen cooking, the wines of Montalcino, a day given over to chocolate, and an afternoon of wine therapy under the Tuscan sun in Cortona. Weekly departures, September through December.

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II October · 10 days

Northern Italy Food & Wine

Lake Garda • Verona • Valpolicella • Bologna • Venice

Autumn in the north is a different Italy altogether. Three nights on Lake Garda in Sirmione as the summer crowds drain away, Verona and the Valpolicella hills where grapes are drying for Amarone, then Bologna for hands-on cooking, Modena's balsamic cellars and Parmigiano straight from the farm. It ends in Venice with a boat day through Murano and Burano, and a farewell dinner in the lagoon light.

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III September – November · 10 days

A Taste of Tuscany & the Italian Riviera

Maremma • Wine Country • Tuscan Villages • Italian Riviera

Two Tuscanys in one journey, both at their best in autumn. It begins in the wild Maremma: Pitigliano and Sorano carved from the tufa, the thermal waters of Saturnia, the great reds of Bolgheri. Then the coast, Portofino and the Cinque Terre after the crowds have gone, before turning inland for the vendemmia heartland of Pienza, Montalcino and Montepulciano, where Brunello and Vino Nobile are made.

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IV September – November · 5 days

Calabria & the Cedri Riviera

Cooking • Local Hosts • Coast • Southern Italian Life

Built with our Calabrese hosts, Gaetano and Antonella, for September through November, when the sea is still warm and the coast belongs to the locals again. You stay in their family villa in Praia a Mare, cook together in the evenings, sail to Dino Island and the Arcomagno caves, and wander Diamante's painted murals and the mountain villages of Tortora and Aieta. Five days at a real Calabrese family table.

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V September – November · 9 days

Kingdom of the Sun

Puglia • Matera • Basilicata • Calabria

The Mezzogiorno keeps its summer long into autumn, and loses the crowds. Nine unhurried days from Polignano a Mare above the Adriatic to the trulli of Alberobello, baroque Lecce and the white lanes of Ostuni, the cave dwellings of Matera in soft October light, then down the coast to Maratea and Tropea. The south at its own pace, with the option to carry the story onward into Sicily.

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Follow the season

September

Vendemmia

The grape harvest sweeps the country: pickers in the rows of the Val d'Orcia, long evenings that still feel like summer, and the coast at its quiet best.

October

Harvest

Wine country at full tilt: grapes drying for Amarone above Verona, truffles arriving in the markets, food festivals everywhere and the best touring weather of the year.

November

Slow Italy

The olive harvest and the first taste of olio nuovo, truffle season at its peak, uncrowded museums and long fireside dinners: the Italy most visitors never meet.

December

Christmas

Rome, Florence and Venice dressed for the holidays, markets in the Dolomites, festive southern tables and a very beautiful way to end the year.

Why travel with IVS

Designed around the Italy you came to feel.

We don’t simply assemble hotels and transfers. We build the days around people, places and moments that make a trip feel personal: the winemaker who opens the cellar after lunch, the driver who knows the road nobody else takes, the cook who teaches you her family’s pasta.

Private itineraries built around you
Local hosts across Italy
Private drivers & door-to-door logistics
Handpicked hotels, villas & agriturismi
Food, wine & cultural experiences
24-hour in-country assistance

Create a Private Journey

“The best journeys through Italy are not always about seeing more. Sometimes they are about arriving at exactly the right moment.”

Italy Vacation Specialists · Est. 2001

Good to know

Questions, answered

When is the best time to visit Italy in the fall?

Each month has its own character. September still feels like summer and the grape harvest is everywhere. October brings truffles and the most beautiful light of the year. November is quiet, local and delicious, and December turns festive from Rome to the Dolomites.

Are these fixed group tours?

Both, by design. Most of the collection is private and starts on your dates, with the pace, hotels and experiences tailored around you. Flavors of Fall in Tuscany runs on weekly departures from the estate, and Kingdom of the Sun offers a genuine small-group way to travel the south, so there is a way in for every travel style.

What is the weather like in October and November?

Mild and often golden. Expect 15 to 22 degrees in October and 10 to 16 in November, cooler in the mountains. It is some of the best touring weather of the year, with a fraction of the summer crowds.

Can you arrange Christmas and New Year trips?

Yes, and they are among our favorites. Rome, Florence and Venice dressed for the holidays, Christmas markets in the Dolomites and long festive tables in the south. December dates book early, so we suggest planning by October.

Your Italy begins here

Tell us how you want Italy to feel.

Share your dates, interests and travel style. One of our Italy specialists will build the journey around you, from the first vineyard morning to the last espresso before the flight home.

Our travel specialists reply within one business day.

I Flavors of Fall in Tuscany
II Northern Italy Food & Wine
III A Taste of Tuscany & the Italian Riviera
IV Calabria & the Cedri Riviera
V Kingdom of the Sun

25 years of private journeys
Local hosts across Italy
Private drivers · 24h assistance
Featured in National Geographic Traveller UK

What interests you most?

The Table in Autumn

This is the season the Italian kitchen was made for. New olive oil on warm bread, white truffle shaved over fresh pasta, chestnuts on the fire and young wine straight from the cellar. Our journeys are built around those tables, from family trattorie to a winemaker’s own kitchen.

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A Note from Your Local Hosts

Autumn is when we take our own families to the countryside. The roads are quiet, the towns are themselves again and every week brings a festival somewhere. Come in this season and you will meet the Italy we grew up with.

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