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September · October · November · Christmas

Italy's Most Delicious Season

Vendemmia, truffles, olive harvest and Christmas

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

4 curated journeys · September - December 2026
Flavors of Fall in Tuscany: Olive Harvest, Truffles, Wine & Cooking
I September · 8 days

Flavors of Fall in Tuscany: Olive Harvest, Truffles, Wine & Cooking

Experience Tuscany during its most delicious season, when the countryside comes alive with the annual harvest. From the grape harvest of September to the olive groves and truffle season of October and November, spend a w...

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The Vendemmia: Tuscany Wine Harvest
II September · 8 days

The Vendemmia: Tuscany Wine Harvest

Cooking with the Stars & Other Ingredients Unique to Tuscany: An in-depth, hands-on cooking 7-day cooking program in Tuscany. In the heart of the Chio valley in Tuscany, come and join us for an intensive program of Itali...

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Tuscany & Umbria in Harvest
III October · 7 days

Tuscany & Umbria in Harvest

This deluxe small group (or private tour ) through Tuscany and Umbria in central Italy offers our guests the possibility to experience two of Italy's most beautiful wine regions as well as Florence. There are many highli...

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Rome & the Amalfi Coast including Vatican City, Island of Capri, Pompeii and the Wineries of Mt. Vesuvius
IV October - November · 7 days

Rome & the Amalfi Coast including Vatican City, Island of Capri, Pompeii and the Wineries of Mt. Vesuvius

Let us help you experience the most beautiful places in Rome and southern Italy which are difficult to reach without a car. Our local English speaking drivers and guides will show you the best of Rome and the Amalfi Coas...

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Follow the season

September

Vendemmia

Grape harvests, late-summer Sicily, Tuscany, Puglia and long evenings that still feel like summer.

October

Harvest

Wine country, truffles, autumn landscapes, food festivals and some of the best touring weather of the year.

November

Slow Italy

Olive oil, kitchens, art cities, uncrowded museums, fireplaces and an Italy most visitors never meet.

December

Christmas

Rome, the Dolomites, southern traditions, markets, festive cooking 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?

No. Every journey in this collection is private and starts on your dates. We tailor the pace, the hotels and the experiences around you, and two of the journeys can also be combined into one longer trip.

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.

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

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.

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.