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Flavors of Fall in Tuscany: Olive Harvest, Truffles, Wine & Cooking Umbria, Italy. Escorted Tours with Italy Vacation Specialists Harvest Time in Tuscany & Umbria

Private · Cortona

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

8 Days Tuscany

This Season September – December A chapter of Italy's Most Delicious Season Featured Journey See the full season
The Overview

Overview

There is a brief and beautiful period each autumn when Tuscany changes.  The vineyards turn gold and red, truffle hunters head into the woods with their dogs, olives are gathered from the trees and the local mills begin producing the intensely green, peppery new olive oil known as 'olio nuovo' and this journey was created around that moment.

THE HARVEST CHANGES WITH THE SEASON

SEPTEMBER — LA VENDEMMIA 

September belongs to the vineyards.

This is grape-harvest season in Tuscany, when the estates are busy bringing in the year's fruit and the cantinas begin the work of transforming grapes into wine.

September departures place greater emphasis on the vineyards, wine production, seasonal gardens and the foods of late summer and early autumn.

Where conditions and the estate permit, guests may have an opportunity to participate in or observe elements of the grape harvest.

OCTOBER — WINE, OLIVES & TRUFFLES

October is perhaps the most varied moment of the season.

The vendemmia may still be finishing on some estates as the olive harvest begins elsewhere. Truffle season is underway, the countryside starts turning gold and the kitchens shift toward autumn.

Depending upon the year, October departures can offer an extraordinary crossover between wine, olives, truffles and the autumn table.

NOVEMBER & EARLY DECEMBER — OLIO NUOVO & THE AUTUMN KITCHEN

Now the olive groves take center stage.

Olives are gathered and brought to the frantoio, where the season's intensely green new olive oil — olio nuovo — emerges.

This is also a wonderful time for truffles and the deeper flavors of the Tuscan kitchen.

November and early December departures focus more strongly on olive oil, truffles, autumn cooking and the wines that have defined this landscape for generations.

Harvest activities vary according to weather, agricultural conditions and the natural timing of each year's crop. We adapt each week's experiences to what is actually happening in Tuscany during your stay.


WHAT MAKES THIS JOURNEY DIFFERENT

This is not simply a food and wine tour through Tuscany. For seven nights, you will make your home on a family-owned wine and olive estate and experience the harvest from the inside — meeting the people who grow, produce and cook with the ingredients that define this region.  The journey changes as the season changes. One week may find us among the vines during the vendemmia; another among the olive trees as the year's new oil is pressed.

Rather than asking Tuscany to follow our itinerary, we allow our itinerary to follow Tuscany.

Duration

8 days

7 nights

Starting From

EUR 5,650

Per person, based on a minimum of 2 travelers

Tailored to your departure and group.

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 week on a family-owned wine and olive estate cooking, tasting, exploring and experiencing the traditions of rural Tuscany as they unfold around you.

Regions
Tuscany
Tour Style
Private
Departs From
Cortona
Meeting Point
Villa
Included Meals
Daily breakfast · 5 lunches · 5 wine tastings · 4 dinners · 2 cooking classes
Day by day

Itinerary

Follow the route as you read. The map traces each day of the journey, moving with you from place to place.

Tuscany

Chapter 1 · Days 1–8

Welcome to Tuscany

Tuscany is among the most beautiful regions of Italy. The gentle curves and slopes of the land will enchant you. Tuscany is as famous for its wine and cuisine as it is for its landscapes. Wine production focuses on red wines like Chianti, San Giovese, Rosso di Montalcino, Rosso di Montepulciano, Bolgheri, and others. Food is prepared with seasonal…

Explore Tuscany
Day 1

Tuscany, Castiglion Fiorentino

Welcome to the Tuscan Countryside:

  • Dinner
Welcome to the Tuscan Countryside: — photo 1 Welcome to the Tuscan Countryside: — photo 2 Welcome to the Tuscan Countryside: — photo 3 Welcome to the Tuscan Countryside: — photo 4 Welcome to the Tuscan Countryside: — photo 5

Welcome to Tuscany and the beginning of a week dedicated to one of the most exciting times of the year in the Italian countryside — harvest season.

Upon arrival, you will be welcomed to your home for the week, a beautiful family-owned estate surrounded by vineyards, olive groves and the rolling landscapes of Tuscany just north of Cortona.  

You will have time to settle into your accommodation and enjoy some time at leisure after your journey. Should the weather be warm enough, take a dip at the villa's spectacular pool or take a walk through the grounds, enjoy the views or simply relax and begin to settle into the slower rhythm of the countryside.

This evening, we come together for a welcome aperitivo followed by dinner featuring the flavors and wines of the region. Over dinner, we will introduce the week ahead and share a little about what is happening locally during this particular stage of the harvest.

From the vineyards of September to the olive groves and truffle season of later autumn, every week brings something different — and tomorrow we begin discovering it.

Meals Included: Welcome Dinner

Where we meet Villa
Day 2

Tuscany

From the Garden to the Tuscan Table

  • Breakfast
  • Lunch
  • Dinner
  • Wine Tasting
  • Cooking Class
From the Garden to the Tuscan Table — photo 1 From the Garden to the Tuscan Table — photo 2 From the Garden to the Tuscan Table — photo 3 From the Garden to the Tuscan Table — photo 4 From the Garden to the Tuscan Table — photo 5

Our first full day begins where Tuscan cooking itself begins: with the ingredients.

After breakfast, discover the estate and learn about its vineyards, olive groves and agricultural traditions before heading into the garden to see what the season has given us.

Tomatoes and zucchini may still be abundant during the earliest September departures. Later in the season, the kitchen changes toward squash, cavolo nero, beans, mushrooms, chestnuts and the ingredients of autumn.

Together with our cook, we select ingredients and take them into the kitchen for our first hands-on cooking experience.

This is not a cooking demonstration.

Roll up your sleeves, prepare the dishes and learn the techniques behind the deceptively simple food Tuscany does so well.

Then comes the best part: sitting down together to eat what we have made, accompanied by wines from the estate.

The afternoon is deliberately left at leisure.

Relax at the estate, walk among the vines and olive trees, or venture into nearby Castiglion Fiorentino for a coffee and a wander through its historic streets.

Day 3

Tuscany, Castiglion Fiorentino

The Harvest

  • Breakfast
  • Lunch
  • Wine Tasting
The Harvest — photo 1 The Harvest — photo 2 The Harvest — photo 3 The Harvest — photo 4 The Harvest — photo 5

Today takes us into the heart of the reason we have come to Tuscany at this particular time of year.

But what we harvest depends upon when you arrive.

During September, the focus is likely to be the vineyards and the vendemmia. We learn how the grapes are harvested, what happens when they reach the cantina and how the year's wine begins its life.

As the season moves into October and November, our attention increasingly turns toward the olive groves.

Join the growers among the trees and learn how Tuscany's olives are gathered. Where possible, participate in the harvest before sitting down for a rustic lunch inspired by the season.

During active olive pressing, we follow the journey from tree to frantoio and see how the fruit becomes extra-virgin olive oil.

There is something extraordinary about tasting genuinely fresh olive oil for the first time.

Intensely green, grassy and peppery, olio nuovo bears little resemblance to the bottles that have spent months traveling around the world.

Drizzled generously over toasted Tuscan bread, it needs very little else.

This is Tuscany at harvest time.

Day 4

Tuscany, Montalcino

Into the Woods: Truffles & Tuscan Cooking

  • Breakfast
  • Lunch
  • Wine Tasting
  • Cooking Class
Into the Woods: Truffles & Tuscan Cooking — photo 1 Into the Woods: Truffles & Tuscan Cooking — photo 2 Into the Woods: Truffles & Tuscan Cooking — photo 3 Into the Woods: Truffles & Tuscan Cooking — photo 4 Into the Woods: Truffles & Tuscan Cooking — photo 5

This morning we leave the vineyards and olive groves behind and head into the woods.

Accompanied by a local truffle hunter and his trained dogs, we learn about one of Tuscany's most mysterious ingredients.

Truffles cannot simply be planted and harvested on command. Finding them requires knowledge of the forest, the trees, the soil, the season — and a very good dog.

After our hunt, we return to the kitchen.

Today's cooking experience is inspired by the flavors of the forest and may include handmade pasta and traditional dishes designed around the truffles and seasonal ingredients available at the time.

Then we sit down for a long lunch accompanied, naturally, by local wine.

The remainder of the afternoon is yours.

Meals Included: Breakfast, Truffle Lunch

. 

Day 5

Umbria, Perugia

Pienza, Montalcino & the Wines of the Val d'Orcia

  • Breakfast
  • Lunch
  • Dinner
  • Wine Tasting
Pienza, Montalcino & the Wines of the Val d'Orcia — photo 1 Pienza, Montalcino & the Wines of the Val d'Orcia — photo 2 Pienza, Montalcino & the Wines of the Val d'Orcia — photo 3 Pienza, Montalcino & the Wines of the Val d'Orcia — photo 4 Pienza, Montalcino & the Wines of the Val d'Orcia — photo 5

Today we venture deeper into southern Tuscany.

Our route takes us through the extraordinary landscapes of the Val d'Orcia — rolling hills, cypress-lined roads, stone farmhouses and medieval towns that have come to define the world's image of Tuscany.

We begin in Pienza, the Renaissance hill town overlooking the valley and home of Tuscany's famous pecorino cheese.

There will be time to explore before continuing toward Montalcino.

This is Brunello country.

Rather than racing from winery to winery, we visit a carefully selected producer where we can understand the territory, meet the people behind the wines and enjoy a proper tasting.

There will be time for lunch and for enjoying the countryside before returning to our estate in the late afternoon.

Meals Included: Breakfast, Wine Tasting

Day 6

Tuscany, Cortona

Cortona & the Val di Chiana

  • Breakfast
  • Lunch
  • Dinner
  • Wine Tasting
Cortona & the Val di Chiana — photo 1 Cortona & the Val di Chiana — photo 2 Cortona & the Val di Chiana — photo 3 Cortona & the Val di Chiana — photo 4 Cortona & the Val di Chiana — photo 5

Today we stay closer to home and explore Cortona.

Perched high above the Val di Chiana, Cortona is one of Tuscany's great hill towns — beautiful, ancient and still very much alive beyond the visitors who come to see it.

Spend the morning discovering its stone streets, piazzas, shops and viewpoints with time to explore independently.

The remainder of the day brings us back to the food and wine culture surrounding Cortona.

Depending upon the final seasonal program, today's experience may include a special cooking experience, winery visit, estate lunch or another encounter with one of the area's producers.

The emphasis remains the same throughout the week: meeting the people behind what we eat and drink rather than simply consuming the finished product.

Day 7

Tuscany

A Final Taste of Tuscany

  • Breakfast
A Final Taste of Tuscany — photo 1 A Final Taste of Tuscany — photo 2 A Final Taste of Tuscany — photo 3 A Final Taste of Tuscany — photo 4 A Final Taste of Tuscany — photo 5

Our final full day is deliberately kept more relaxed.

By now, Tuscany should feel a little less like somewhere you are visiting and a little more like somewhere you have been living.

Today gives us room to incorporate something particularly special from the season.

It might mean returning to the olive groves during an active harvest, visiting a small producer, discovering a local market, tasting cheeses with the people who make them, or enjoying another experience connected to what is happening in the countryside that week.

There will also be time to relax at the estate, pack, take a final walk through the vineyards or simply sit outside with a glass of wine.

Tonight we gather one last time for our farewell dinner.

A week ago, most of us arrived as strangers.

Tonight we sit down around one Tuscan table.

Meals Included: Breakfast, Farewell Dinner

Day 8

Arrivederci Toscana

  • Breakfast

Enjoy breakfast at the estate before checking out this morning.

Private transfers can be arranged onward to the railway station, Florence, Rome or your next destination in Italy.

And if you are traveling during olio nuovo season, we suspect there may be a bottle or two of Tuscan olive oil making the journey home with you.

Meals Included: Breakfast

The details

Inclusions & Exclusions

What's Included

  • Cooking class
  • Pic-Nic in the Olive Groves
  • Specialized and Personal Service
  • Stay in Luxury Villa in Tuscany
  • Tasting Menu
  • Tastings of local products
  • Wine and Olive Oil Tastings

What's Not Included

  • Gratuities of any type
  • International fights
  • Meals not mentioned in the program
  • Optional excursions during your tour
  • Travel Insurance
In their words

Traveler Reviews

Emily and David Davison Travelled with us

My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She planned the perfect trip with excellent private guides at all of our sites, professional drivers and lovely hotels. We arrived in Italy with all of our train and ferry reservations made by Ele, with tickets in hand. She was in touch with us daily throughout our trip to make sure that things were going smoothly. She was able to make a few changes to our itinerary as needed. We look forward to working with Ele again on our next trip and have put her in touch with another family member to help plan their trip as well.

Ron and Deb Crosby Travelled with us

Dear Guiseppe and Jesse,

We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future.

Hotels

1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were part of their family. I would recommend it to anyone and would specifically ask for it if we were to make a return visit.

2. Hotel La Baia in Monterosso was nice and it's location was very good especially for us older folks humping luggage from/to the train station.

3. Hotel Lucchesi in Florence- what can I say expect FANTASTIC. The rooftop view at sunset is well worth it. Again very friendly and helpful staff. Would recommend it to everyone.

Wine Tour

Money well spent. We had a great time overall. The driver Mario was OUTSTANDING. He had lots of local knowledge as well as about winemaking. USE HIM AGAIN!!!

The various wineries we visited on tour:

Altesino- fantastic and they were not cheap on their pouring. Great experience.

Azienda Agricola Patrizia Cencion Sloaria- Again a great tour by one of the owner's daughters. We felt like we were the only thing on their mind although there were other customers there. A great way to complete the day.

Again we had a fantastic time and are very appreciative of everything you booked for us. We wish you continued success and if our travels should bring us back to Italy, we know who to call.

Leon and Michele Travelled with us

The trip was great we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.

Bob & Sandy Travelled with us

Jesse & Giuseppe,

Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.

Where you are

Location

Italy Cortona

Cortona and beyond

8 days through Italy, with every stop chosen by the people who live here.

Where we meet

Villa

Where it starts

Cortona

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Highlights of Tuscany: Gourmet Food and Wine Package
Highlights of Tuscany: Gourmet Food and Wine Package
A Taste of Tuscany & Cinque Terre: Food, Wine & the Italian Riviera
A Taste of Tuscany & Cinque Terre: Food, Wine & the Italian Riviera
Saints and Sinners: A Sacred Journey Through Rome and Beyond
Saints and Sinners: A Sacred Journey Through Rome and Beyond
Good to know

Frequently Asked Questions

Is this a private tour, or will we join a group?

Private. You travel with your own guide and driver, and the only people on the itinerary are the ones you bring with you. Nothing is shared with strangers, and the pace of each day is yours to set.

Can the itinerary be changed to suit us?

Yes. What you see here is a starting point, not a fixed departure. Tell us how long you have, what you love and what you would rather skip, and we will reshape it around you. A slower morning, an extra night somewhere you fell for, a different region entirely.

How do we start planning?

Send us a note using the form on this page, or call us on 1-866-779-2565. A travel specialist replies within one business day, usually with a few questions of their own. There is no cost and no obligation in asking.

When should we book?

The earlier the better, particularly for travel between May and September, when the best small hotels and the guides worth having are taken first. That said, we have put together beautiful trips at short notice, so ask and we will tell you honestly what is still possible for your dates.

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