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9 Days Wine Tasting and Culinary Holiday in Italy

Italy Cooking Vacation

Experience Italian cooking and the Tuscan way of life. During the trip, you will spend time visiting with many locals food and wine and learn how small the world really is. The tour focuses on the Chianti region between Florence and Siena, Val d’Orcia, Montalcino and Pienza, and San Gimignano. With guides Linda Harmon and Chef Doug Mack, you will meet new friends and experience Tuscany like a local. It's going to be your once in a lifetime experience.

Meet the instructors

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  • Olive oil tasting
  • Prosciutto tasting
  • Wine tours and tastings
  • Hands-on Tuscan cooking classes
  • 8 nights accommodation
  • Guided city tours
  • Daily meals


8 days with instruction in English
Spoken languages: English
The maximum participants in the group is 6
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During the trip, you will stay at Tuscan agriturismo and small bed and breakfast around Tuscany, Italy.


The tour begins in the morning when you are greeted at the Florence airport and you are together with others heading south through the Chianti region along the Via Chiantigiana. You will stop along the way at picturesque villages for shopping and photo shoots and getting a feel for the rhythm of the country.

Daily schedule

Day 1

First stop is Greve, gateway to the Chianti region. After a morning cappuccino, you will go to Panzano to visit the bustling farmers market where you will pick up some treats for a light meal later in the afternoon. With lunch treats in hand, you will continue to Castellina in Chianti, a stroll through town and the first of many gelato stops.

Late afternoon, you arrive at your agriturismo accommodation just outside of Siena where you will spend your first two nights. Dinner in the evening is at a chef-owned slow food restaurant specialized in Sienese specialties.

Day 2

After breakfast at the agriturismo, you will head back into Siena for two-hour cultural and historical tour of the well-preserved medieval city of Siena, a UNESCO world heritage city, followed by lunch at slow food restaurant. Late afternoon, you will leave Siena and return to the agritourismo for a hands-on cooking class. After the cooking class, you will join a wine tour. Enjoy the wine tasting and finish with the class-prepared dinner paired with the famous Chianti wines.

Day 3 and 4

After breakfast, you will head south toward the Val d’Orcia, an area renowned for wine production and farming. The land is characterized by gentle hills and valleys dotted with picturesque towns and villages. One of these villages is Montalcino which welcomes you with its elegant, world renowned Brunello wine, and its younger Rosso di Montalcino.

Later in the day, you will arrive in Pienza where you will stay at for the next two days. This Renaissance gem is a beautiful little town rebuilt as an “ideal town” in the 15th century under the direction of Pope Pius II.

Day 5 and 6

After breakfast, you are off to visit a nearby organic agritourismo that raises sheep and goats to produce Pecorino. A farm tour, cheese tasting, and terrific vegetarian lunch while enjoying beautiful views of Val d’Orcia. Afterwards, you will visit Montepulciano, known for another renowned wine, Nobile di Montepulciano. There will be wine tasting, walking, and free time. Then you return to Pienza to visit Palazzo Piccolomini, family home of Pope Pius II.

Day 7 and 8

After breakfast, you are off to San Gimignano, one of the most photographed hill towns in Tuscany where you will be staying at for two nights.

Day 9

Before leaving the village, you will make another gelato stop, a little gelateria that Lonely Planet called as one of the top 10 places in the world not to miss in the food category.


Doug Mack
Doug Mack, together with his wife, Linda Harmon, is the owner of Mary's Restaurant at Baldwin Creek in Bristol, Vermont. Mary's is open all year round, closing for a week and a half in November and April. From May to October, they cater events such as weddings, rehearsal dinners, and anniversary parties. Working together in a different role, Mack is more of a man who stands at the back of the house, overseeing cooking, menu development, and maintenance. He likes being busy and likes the satisfaction of making people happy.


The culinary holiday will be held in several beautiful and interesting places in Tuscany, Italy including Chianti region between Florence and Siena, Val d’Orcia, Montalcino, Pienza, and San Gimignano.



  • Cooking classes
  • Cycling nearby
  • Golf course nearby
  • Hiking nearby
  • Horse riding / rental nearby
  • Massage
  • Mountain walking / trekking nearby
  • Outdoor swimming pool
  • Sauna
  • Shopping nearby
  • Spa
  • Swimming


  • Tour assistance


During the trip, you will be served three daily meals including wine.

The following meals are included:

  • Breakfast
  • Lunch
  • Dinner

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

Things to do (optional)

  • Cycling
  • Explore surrounding areas
  • Hiking
  • Join local festivals
  • Shopping
  • Trekking
  • Visit local markets
  • Visit museums
  • Wine tasting

What's included

  • 3 daily meals
  • 8 nights accommodation
  • Cheese and olive oil tastings
  • Daily cooking class
  • Wine tours and tastings
  • Guided village tours with local guides

What's not included

  • Airfares
  • Airport transfers
  • Optional activities

How to get there

Arrival by airplane

Please book your flight to arrive at Florence Airport (FLR). Transfer from and to the airport is available upon request.

Cancellation Policy

  • A reservation requires a deposit of 15% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 120 days before arrival.
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