Villa On A Tuscan Hill™

Food & Wine In The Land Of Siena ~ 7 Day

Join Signora Stefania in our Food & Wine In The Land Of Siena program set in an 18th century Villa on the hills of Montepulciano.  Once home to a noble family of Siena, the Villa is nestled between tall cypress trees, green gardens and an endless view overlooking the gentle hills of Val d’Orcia.

Delicious Tuscan food, wine and culture are featured in this Tuscany food and wine tour that takes you through the countryside of Val d’Orcia, Pienza, Montalcino, San Gimignano, and the ancient village of Montepulciano for a food and wine vacations.  Discover hearty cuisine in our hands-on cooking classes, sip and swirl prized Tuscan and Brunello wine while visiting vineyards and landmarks in beautiful Montepulciano.

The Food & Wine In The Land Of Siena program immerses you into the local lifestyle while you soak up the traditions of great Tuscan cuisine.  The entire Villa and gardens have been fully restored with every modern comfort while keeping its Old World charm.

Signora Stefania welcomes each guest to her home and kitchen where she shares a little bit of history, cooking technique and conversation in this one-of-a-kind authentic tour.  Cook, tour and make new friends in dreamy Tuscany.  Her soft words for each guest are, “this villa is but a home that we wish to share with guests, where life is simple, the silence magical, and the daily pattern of one’s days follows the rhythms of nature.”  Step into magical Tuscany and let the cooking begin!

Tuscan Cooking Classes

Hands-on cooking classes focus on all ingredients being local – with vegetables and fruits from the garden property and Tuscan products from the finest purveyors including artisan cheese makers, butchers, bakers and wine makers.  In each cooking class you will learn how to prepare antipasti, fresh pasta and sauce, a main course and dessert.

Tuscan antipasti include: torta salata, a savoury flan; traditional crostini toscani, bruschetta toasted breads made with fresh tomatoes and herbs, olives; and fegatini, Tuscan chicken liver, along with regional capocollo, and artisan cheese.

Signora Stefania and Chef Massimo will guide you in the kitchen preparing fresh pasta and sauce such as pici all’aglione – Tuscan pasta and a special sweet garlic sauce Pasta recipes include ravioli nudi amd tagliolini alla frantoiana, pasta with olive oil and herbs, to name a few.

You’ll learn the secret recipe for ribollita Toscana, a slow-stewed soup made with a variety of fresh vegetables and toasted bread.  Ribollita, translates to re-boiled, and Tuscan cooks and chefs traditionally add vegetables and meat to the soup day after day.  Pappa al pomodoro, bread and tomato soup is another classic recipe that everyone loves to make.

Tuscan main courses include, bistecca fiorentina, a unique Tuscan cut of meat from the white cow called a chianina.  This breed of cows live in Val di Chiana, Tuscany. Another famous recipe includes cinghiale, wild boar, piccione, pigeon, and anatra, duck. There is also scottiglia, a traditional main course featuring an assortment of rabbit, chicken, veal, pork, pigeon, lamb and turkey.  Wild chicken served with local olives of Grosetto (olives that are cured in brine and marinated with grated orange zest, fennel and a little garlic) prepared with herbs is another typical Tuscan recipe.  Beans such as cici, all’uccelleto and pizelli novelli, and faro, are also a staple in the Tuscan diet and make delicious Vegetarian meals.

You’ll learn how to make lovely desserts including bongo, Tuscan chocolate profiteroles;  bomboloni, a Tuscan doughnut and cantucci, twice baked cookies, traditionally dipped in Vin Santo.  Tuscan desserts are endless: stracciata alla fiorentina, a sweet pizza, and pannello con l’uva, a brioche bread made with grapes and usually served during the time of the harvest, totra di mele, an apple flan and pinocchiati, pine nut crips to name a few. These are a small sample of Tuscan recipes that you will prepare – each recipe can easily be recreated in your home kitchen.

The Luxury Villa

Set on a crest above gentle rolling Tuscan hills, the Villa is a property of splendour.  Signora Stefania and her family renovated the 18th century property taking much care to keep every element of its Old World charm.  Spacious gardens spanning 15 acres, cypress trees peppering the property and green gardens filled with antique vases and marble fountains make the Villa a magical place.  An elegant breakfast room offers fresh cakes, biscotti, tarts and flans each morning.  Pecorino cheeses, Tuscan cured meats, eggs, farm bread, caffe, tea and fruit juices are also served.

The Villa’s rooms, ensuite with complete private baths, are bright, oversized and spilling with natural sunlight.  Rich tapestries, drapes, bed comforters – each made by hand for each room – will have you slipping back and relaxing.  Modern comforts including satellite TV, a safety strongbox, mini-bar, internet and telephone, are included in each room suite.

Guests are invited to stroll the gardens and swim in the magnificent marble swimming pool decorated with Florentine statues and water fountains (weather permitting).

Conveniently located in the heart of Montepulciano, the Luxury Villa or the Garden Villa are a short distance to Siena, Florence, Perugia and Assisi, as well as Pienza, Monticchiello, Montalcino and Cortona making it the perfect location.  Guests who visit in autumn can try their hand at truffle hunting on the 15 acres of property.


The Garden Villa

Check into the luxurious Garden Villa In Montepulciano – set in a beautiful Tuscan garden in the heart of Montepulciano.  Signora Niccolo and his family welcome you to the property – just a short 10 minutes walk from Montepulciano’s historic centre.  Beautifully decorated large rooms have every comfort – lots of light, privacy and ensuite baths.  The property boasts 18th-century charm from its historic past, while offering modern amenities and complimentary wi-fi.

Tuscany is known for many things, but most of all for its Chianti Classico, the Vino Nobile di Montepulciano, the Brunello di Montalcino and the Vernaccia di San Gimignano. During your stay enjoy a wine tasting at the property with some of the finest vintages that the wine cellar has to offer.  Sip and swirl Barolo – Porta Rossa, Chianti Classico – Borgo Pretale, Pinot Grigio – Gaierhof, Prosecco – Banear, Amarone – Corte Vecchia Verdicchio dei Castelli di Jesi – Bonci and Vernaccia di San Gimignano – Signano to name a few.  


Tuscany has been the cradle of the arts and banking throughout time from the Etruscans to  the Medici Family.  Discover the landscapes and history of this region as you visit and tour the nearby town of Montepulciano, called “Jewel of the Renaissance.”

Visit Pienza, a small town known for its artisan cheese, quaint caffes and small shops with handmade crafts. There’s also Chiusi, which offers its history, open-air museum with tombs.  Montalcino, also an interesting town to visit,  is known for its great Fortress.  A must see town is Montalcino, known for its famous Brunello di Montalcino.  During your Tuscany cooking classes, we encourage you to visit the nearby towns of Arezzo, Cortona, Siena and San Gimignano.

Itinerary: 7 days, 6 nights

Day 1: Arrival & Tuscan Welcome Dinner

  • Pick up at the Chiusi-Chianciano train station.
  • Arrival to the Villa, check-in, relax.
  • Welcome Prosecco on the terrace overlooking the rolling hills of Val d’Orcia.
  • A Chef’s Welcome Dinner featuring Tuscan cuisine with a toast of local red or white wine, included.

Day 2:  Montepulciano & Cooking Class 1

  • Breakfast is served.
  • Transfer to Montepulciano with your driver.  Take a stroll through the beautiful cobblestone streets before staring your cooking class.
  • Cooking Class 1, tie on your aprons and get cooking preparing your Tuscan menu.
  • Lunch follows and includes the foods that were prepared in the cooking class 2.  Local red or white wine included.
  • After your cooking class, take time out to visit Montepulciano.   Later, return to the Villa with your driver.
  • Relax at the Villa.  Later in the evening, enjoy artisan cheese, salumi, Tuscan bites and bottle of Tuscan wine, included.

 Day 3: Food Lover’s Landmark Tour of Montepulciano

  • Breakfast is served.
  • In the morning, meet your English-speaking guide for your Food Lover’s Landmark Tour of walking through Montepulciano. Learn about the food, culture and landmarks of your host city, all with tastings included along the way.
  • Return to the Villa.  Relax.
  • Dinner is on your own.  Suggestions are provided.

Day 4:  Cooking Class 2 & Food Lover’s Walking Tour of Pienza

  • Breakfast is served.
  • In the morning, Cooking Class 2.  Tie on your aprons and get cooking.  You will prepare a complete Tuscan menu.
  • Lunch follows and includes the foods that were prepared in the cooking class.  Local red or white wine included.
  •  After your cooking class, your private driver and guide takes you to Pienza.  Pienza is a quaint charming town, the birthplace of Pope Pius the II, and home to artisan cheese makers and artists. Enjoy a Food Lover’s Walking Tour of Pienza, with tastings included along the way. 
  • Following Pienza, your driver continues through Tuscan roads and returns to the Villa.
  • Relax at the Villa.
  • Later in the evening, enjoy artisan cheese, salumi, Tuscan bites and bottle of Tuscan wine, included.

Day 5:  Cooking Class 3

  • Cooking Class 3.  Tie on your aprons and get cooking preparing your Tuscan menu.
  • Lunch follows and includes the foods that were prepared in the cooking class.  Local red or white wine included.
  • Afternoon is free to relax by the pool, walk in the gardens or sit back and enjoy the landscape overlooking the Val d’Orcia valley.
  • Dinner is on your own.  Suggestions are provided.

Day 6: Tour to Cortona, Wine Tour Tasting & Lunch

  • Breakfast is served.
  • Following breakfast, your driver takes you to Cortona, the small town made famous by Frances Mayes in her book, “Under The Tuscan Sun.” Visit the town, take in artisan shopping, stop in a wine bar for a glass of red or white or a cappuccino and sweet.
  • Following Cortona, your driver continues  a prized Tuscan winery where the wine makers are known for wine, art and nature set on a beautiful Tuscan vineyard.  Lunch and tastings included.
  • Dinner is on your own.  Suggestions are provided.

Day 7: Departure

  • Breakfast.
  • Check-out and transfer to Chiusi train station.

Add on a day or two and explore Luca or Siena with our private driver, extending your stay in beautiful Montepulicano. Please inquire and we’ll be happy to assist.

*This schedule may vary due to weather, feast days, market days, openings and closings of vineyards, etc.  If you happen to have a specific private activity in mind, please let us know so we can check your final itinerary.

Program Includes:
  • 7 days, 6 nights accommodations, based on 2 guests. Click To View!
  • Daily breakfast and maid service.
  • Round trip transfers to and from the Chiusi-Chianciano train station to the Villa.
  • Welcome dinner including a Chef’s Tasting menu with a toast of wine included.
  • 2 light Tuscan dinners including salumi and artisan cheese, salad and a bottle of wine.
  • 3 cooking classes followed by lunch or dinner with wine included.
  • Montepulciano Food Lover’s Landmark Tour with guide and tasting included.
  • Visit to Pienza with English- speaking driver and guide for a Food Lover’s Tour with tastings included.
  • Visit of the beautiful town of Cortona with driver, made famous by the movie “Under the Tuscan Sun.”  Winery tour and lunch included.
  • Cooking Vacations welcome bag with chef’s apron and recipes.
Program Prices

The Luxury Villa

$3,895 per person, based on 2 guests in the Petite room at the Luxury Villa.

$4,295 per person, based on 2 guests in a Classic Garden room at the Luxury Villa.

$4,395 per person, based on 2 guests in a Superior room at the Luxury Villa.

$4,595 per person, based on 2 guests in a Suite at the Luxury Villa.

$4,795 per person, based on 2 guests in a Super Luxe Suite room at the Luxury Villa.

The Garden Villa 

$3,895 per person, based on 2 guests in a Superior room at the Garden Villa.

From the Garden Villa guests walk to the welcome dinner and cooking classes.

For Single Guests: If you are traveling on your own, please call us for the best group price. We are happy to welcome you into an already scheduled group.

Check Availability

2024 Dates: This program is available throughout the year.  Rates are subject to change based on currency exchange. Call for updated rates. Airfare not included. Group transfers for any cooking tour or tours that include transfers, are for the group and are not private. Transfers before, after or to another destination outside of your cooking tour are not included in the program price. If you would like to add on a private transfer or transfers, let us know and we will send you pricing.