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Cooking Among the Olive Trees in the Spectacular Southern Tuscany A true garden to kitchen cooking experience in Tuscany

Private · Cortona

Flavors of Fall in Tuscany: Cooking, Truffle Hunting, Chocolate, Olive Oil and Wine Therapy on private 100% Tuscan owned organic estate with weekly departures

7 Days Tuscany · Umbria · Tuscany

The Overview

Overview

This is an exclusive experience for food and wine lovers that we offer during the olive harvest and truffle festivals, which take place all over Tuscany during November. During this time, the flavors of fall in Tuscany are at their finest. Experience daily cooking and wine tastings and incredible in-depth knowledge about the best ways to use the local ingredients here in Italy or at home.

For those interested in hands-on cooking, getting into the olive orchards, hunting truffles, and learning about the traditions of  Tuscan cuisine, this is truly a great opportunity to stay with a local Tuscan family, pick local vegetables directly from the garden, which will be used in a variety of dishes, and experience a stay-in-luxury-villa in Tuscany.  

Our package includes the following unbeatable features:

  • Seven nights stay ( with exclusive use of the villa - min. four pax) with arrival on Saturdays or Sundays
  • Each room has en-suite bathroom 
  • Daily Cleaning at the villa 
  • Exciting half-a-day harvest on the Estate (special rake and gloves provided) 
  • Picnic Lunch among the olive trees with a breathtaking view of the valley (beverage included)
  • Visit of the Olive mill
  • Truffle Hunting 
  • Various Wine Tastings 
  • Truffle hunt and local festival

Tasting menu: 

  • Bruschetta with new olive oil and garlic mousse
  • Octopus salad with olives
  • Stuffed Ravioli with Olive oil and black cabbage with a Burrata soup
  • Breast-lacquered duck with green olives
  • Tartelet with olive oil and custard

Weekly prices per person based on four pax: 1450 Euro 

Weekly price per person based on six pax: 1200 Euro 

Weekly price per person based on eight pax: 950 Euro

This package offers excellent value for money and provides those interested in Tuscan cuisine the opportunity to learn about the production of olive oil.  

Duration

7 days

6 nights

Starting From

EUR 4,650

Per person for two travelers

Tailored to your departure and group.

This is an exclusive package we offer during the olive harvest and truffle festivals, which take place all over Tuscany during the month of November when the flavors of fall are at their finest. Experience daily cooking, wine tastings, and incredible in-depth knowledge about the best ways to use the local ingredients here in Italy or at home.

Regions
Tuscany · Umbria · Tuscany
Tour Style
Private
Departs From
Cortona
Meeting Point
Villa
Included Meals
Daily breakfast · 5 dinners · 5 lunches · 5 wine tastings · 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 1–4

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

Independent Arrival in Tuscany at the Estate - Welcome Dinner & Orientation of the Week Ahead

  • Dinner
Independent Arrival in Tuscany at the Estate - Welcome Dinner & Orientation of the Week Ahead — photo 1 Independent Arrival in Tuscany at the Estate - Welcome Dinner & Orientation of the Week Ahead — photo 2 Independent Arrival in Tuscany at the Estate - Welcome Dinner & Orientation of the Week Ahead — photo 3 Independent Arrival in Tuscany at the Estate - Welcome Dinner & Orientation of the Week Ahead — photo 4 Independent Arrival in Tuscany at the Estate - Welcome Dinner & Orientation of the Week Ahead — photo 5

The vineyard and olive groves lie in the center of the narrow Chio Valley, with our independent villas dotting the surrounding hillsides.  Renting a car to come here will ensure the most significant amount of freedom and flexibility, though we can happily arrange private transfers if you prefer.

In the afternoon, we will be waiting to welcome you at the reception, where you will meet our team, who will show you around the property, let you know what to expect over the week, and introduce you to the other participants.

Once you have settled in, we will gather at the former olive mill for a warm Tuscan welcome dinner. The dinner will include a variety of local delicacies like wild boar, ribollita, pappa al pomodoro, lardo di colonnata, and, of course, the local wine made right here on the estate.

Overnight at the estate. 

Where we meet Villa
Day 2

Tuscany, Castiglion Fiorentino

True Garden to Kitchen Cooking with 100% Organic Veggies

  • Breakfast
  • Lunch
  • Dinner
  • Wine Tasting
  • Cooking Class
True Garden to Kitchen Cooking with 100% Organic Veggies — photo 1 True Garden to Kitchen Cooking with 100% Organic Veggies — photo 2 True Garden to Kitchen Cooking with 100% Organic Veggies — photo 3 True Garden to Kitchen Cooking with 100% Organic Veggies — photo 4 True Garden to Kitchen Cooking with 100% Organic Veggies — photo 5

After breakfast at the villa this morning, we will start the day learning about the farm itself, why the Medici family from Florence invested so much in this territory, and why the land is considered some of the most fertile and prosperous in Italy today.

Next, we will walk through the estate's organic vegetable garden, picking fresh, seasonal vegetables that will form the basis of today's lesson.

After carefully choosing your vegetables for the dishes ahead, step into the kitchen with your master chef to begin preparing our dishes of the day, accompanied by local wines!  These are hands-on lessons where everyone has their cooking station, not cooking demonstrations where you watch the chef having fun!

You will have the rest of the day at leisure.  You can either go into Castiglion Fiorentino for dinner, take some more veggies back to the villa, or prepare dinner in the kitchen as night falls in the peace and seclusion of the beautiful Tuscan hills.

Day 3

Tuscany, Castiglion Fiorentino

Into the olive groves

  • Breakfast
  • Lunch
  • Wine Tasting
Into the olive groves — photo 1 Into the olive groves — photo 2 Into the olive groves — photo 3 Into the olive groves — photo 4 Into the olive groves — photo 5

Today will be spent learning about the olives, the process of producing oil and how to pick a good oil.

This morning will be spent out in the fields with the olive growers, where you will be helping harvest the fruit.  Fun, but hard work, you'll be ready to relax and enjoy a hearty lunch in the shade of the olive trees (weather permitting).

In the afternoon, you'll look at the finished product and learn about the characteristics of the olive oil produced here and those produced in other parts of the country.  Olives are grown the length and breadth of Italy, in all its diverse terrains and climates, in fact, Italy has over 350 varieties of olives, amounting to 25% of the olives grown worldwide and every Italian will tell you their regional oil is the best!  By the end of the afternoon, you will be able to judge for yourself whether you prefer the fruity Tuscan or the milder Ligurian oil.

Day 4

Tuscany, Montalcino

Morning Truffle Hunt followed by the Wines of Montalcino

  • Breakfast
  • Lunch
  • Dinner
  • Wine Tasting
  • Cooking Class
Morning Truffle Hunt followed by the Wines of Montalcino — photo 1 Morning Truffle Hunt followed by the Wines of Montalcino — photo 2 Morning Truffle Hunt followed by the Wines of Montalcino — photo 3 Morning Truffle Hunt followed by the Wines of Montalcino — photo 4 Morning Truffle Hunt followed by the Wines of Montalcino — photo 5

Today our day starts early as we will take you into the woods with the truffle hunters and their dogs to search out the mysterious tartufo.  At this time of year, the hunt is for the more expensive white truffles.

Afterwards, we'll be heading into the kitchen to learn how to make some local truffle-based dishes using the larger black truffles, including some homemade pasta.  After the class, all the chefs will sit down for lunch with a few glasses of local wine.

In the afternoon we head into the beautful Orcia valley where we will visit a number of different local wine producers and incredible towns like Montalcino, Montepulciano, Pienza, Montichiello and others.

Here, you will have the opportunity to sample the wines of many local wine producers. 

Return in the evening to the estate for light dinner and overnight. 

Umbria

Chapter 2 · Days 5–5

Welcome to Umbria

Umbria is one of the most beautiful regions in central Italy. South from Florence, north from Rome, it is often referred to as 'Italy's green heart', for it is the geographic center of the county.   it's lovely countryside and rolling sea of valleys and rolling hills are totally land-locked between the regions of Tuscany, Lazio and Marche .  Italy's capital…

Explore Umbria
Day 5

Umbria, Perugia

Cooking with Chocolate in the City of Chocolate!

  • Breakfast
  • Lunch
  • Dinner
  • Wine Tasting
Cooking with Chocolate in the City of Chocolate! — photo 1 Cooking with Chocolate in the City of Chocolate! — photo 2 Cooking with Chocolate in the City of Chocolate! — photo 3 Cooking with Chocolate in the City of Chocolate! — photo 4 Cooking with Chocolate in the City of Chocolate! — photo 5

After breakfast at the villa, we will visit the nearby hilltop city of Perugia, in the neighboring region of Umbria.   You will have some free time to explore the city, indulge in some shopping and have lunch at your leisure.

Throughout Italy, the city of Perugia is famous for its Perugina chocolate and the annual chocolate festival held here each autumn.  This afternoon, we will take a visit to the Perugina Chocolate Factory for a tour of the museum and a chance to taste the chocolates produced here.

Tuscany

Chapter 3 · Days 6–7

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 6

Tuscany, Cortona

Under the Tuscan Sun Cortona & Wine Therapy at an Incredible Spa

  • Breakfast
  • Lunch
  • Dinner
  • Wine Tasting
Under the Tuscan Sun Cortona & Wine Therapy at an Incredible Spa — photo 1 Under the Tuscan Sun Cortona & Wine Therapy at an Incredible Spa — photo 2 Under the Tuscan Sun Cortona & Wine Therapy at an Incredible Spa — photo 3 Under the Tuscan Sun Cortona & Wine Therapy at an Incredible Spa — photo 4 Under the Tuscan Sun Cortona & Wine Therapy at an Incredible Spa — photo 5

Today we will visit the nearby town of Cortona, home to the Baracchi family wine estate.  Here, the day will start with a cooking lesson with Michelin-star chef, Silvia Baracchi.  In the warmth of her kitchen, you will examine the way that you look at food and learn to make delicious local recipes that you can easily reproduce and adapt in your own kitchen.

At the end of the lesson, all the chefs will sit down together to enjoy lunch and a few glasses of the wine from the Baracchi's vineyards.

The afternoon will be have a more relaxing pace, as we try out the wine therapy offered here.  Once the wine has been made, plenty still remains from the vines and the grapes which have both been found to have wonderful antioxidant, rejuvenating properties and are used to create moisturizing creams and relaxing baths.  Lie back in a 'wine bath' and let your cares drift away.

Return to the villa for an evening at leisure.

Day 7

Tuscany

Time to Say Goodbye!

  • Breakfast
Time to Say Goodbye! — photo 1 Time to Say Goodbye! — photo 2 Time to Say Goodbye! — photo 3 Time to Say Goodbye! — photo 4 Time to Say Goodbye! — photo 5

After breakfast this morning it will be time to say goodbye and conclude our services. 

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

7 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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Wine Estates, Culture and Fun in Tuscany and the Cinque Terre!
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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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