A Midsummer Night's Dream Montepulciano™

Tuscan Food & Wine Trails Tour ~ 5 Days

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Stroll along the cobblestone walkway and into the Medieval town of Montepulciano!  Tie on your apron for a week of hands-on cooking classes, pasta making and enjoying Tuscan wine including Brunello and Sangiovese.  Learn how to prepare delicious Tuscan recipes with our award-winning Chef in small groups.  Set on a beautiful hilltop, Montepulciano overlooks the Val D’Orcia and is surrounded by endless fields of sunflowers and silvery green vineyards.

Tuscan Cooking

Step into our Tuscan kitchen and get ready for hands-on cooking classes, pasta making and wine tasting – think Brunello and Sangiovese!  Learn about Tuscan’s food history, while rolling out fresh pasta and making seasonal sauces, main courses and delicious desserts.  Menus follow the rhythms of season using farm-to-table vegetables and produce.  Learn how to prere Pici with ragù, hand-made ravioli stuffed with a ricotta and walnuts or tagliatelle with Porcini mushrooms.  Learn how to prepare bistecca di chianina, Florentine steak along with Chianti sauce and beans all’uccelletta.  Desserts are delicious – and you will learn how to make classic cantuccini– biscotti dipped in Vin Santo, schiacciata con l’Uva, and Chianti wine biscotti.  Following each cooking class, enjoy the food that was prepared in the cooking class with selected Tuscan wine included.  Cooking classes start at 9:30am and last approximately two hours.


Montepulciano is a Medieval Renaissance town on a hill in the Siena region. The name of Montepulciano, according to legend, was founded by the Etruscans.  Rolling Tuscan hills, endless vineyards, silvery green olive trees, and fields of sunflowers surround the village.  From its viewpoints, you can forever see the Val d’Orcia and tall cypress in shades of green.  The Torre di Pulcinella, a clock tower with Pulcinella (the Neapolitan character from the Commedia dell’Art of the 17th century), stands guard over the village.  The town is filled with enotecas, restaurants, artisan food halls, and leather and linen shops.  A resident cellist plays Melodrama in the piazza.  The small hamlet is home to the Palazzo Comunale and the Palazzo Tarugi, along with the ancient churches of Santa Lucia, Santa Maria Assunta, and Santa Maria delle Grazie, decorated with Renaissance art.  The Museo Civico di Montepulciano showcases a collection of archeologic items, paintings, and terracotta by the Della Robbia family.  The Madonna di San Biagio church, an iconic 16th-century landmark, is on the road outside the city.  Montepulciano is known for its Super Tuscan wine, excellent farm-to-table cuisine, ancient history, and passionate locals who welcome guests with open arms.  

Montepulciano Accommodations

Garden Villa In Montepulciano

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.

In both properties, a traditional Tuscan breakfast is served with fresh baked breakfast pastries, fruit, cereals, coffee, tea and jams.

Deluxe B&B

Settle into your deluxe room set in the center of Montepulciano.  Each room is offers antique furnishings and breathtaking views of the two valleys and the lakes of Trasimeno, Chiusi and Montepulciano.  Large private rooms have en-suite bathrooms adorned with linens and bath towels for your comfort. Luxurious furnishings adorn each of the suites.  Check in, unpack and enjoy your stay – just steps away from the Piazza Grande in the heart of Montepulciano.

Luxury B&B

Nestled in the iconic historical center in the village of Montepulciano, this enchanting boutique villa property offers the perfect mix of historic charm and modern luxury, all within a magnificently restored Renaissance palazzo. Each suite is adorned with comfortable hypoallergenic bedding dressed in Italian linens surrounded in luxury overlooking a local neighborhood.

The dreamy accommodation boasts al frescos with exquisite furnishings and bespoke decorations that create an atmosphere of sophistication and refinement. Every room offers a private ensuite bath, air conditioning, internet TV, fast Wi-Fi and soundproof and insulated windows guaranteeing a tranquil and undisturbed night’s sleep. Each morning, guests are greeted with a complimentary gourmet breakfast including Tuscan bread and cakes, fresh fruit, cappuccino, tea, marmalades and jams.


Itinerary~ 4 Nights and 5 Days


Day 1: Arrival, Chef’s Tuscan Welcome Dinner

  • Arrival transfer to Montepulciano and check in.
  • Relax.  Review your itinerary and welcome bag.
  • In the evening, your Chef’s Tuscan Welcome dinner isa full course dinner.  Additional wine and beverages are available at a surcharge.

Day 2: Cooking Class 1 & Montepulciano

  • Breakfast is served.
  • Tie on your apron for Cooking Class 1 for a Fresh Pasta Menu. This hands-on cooking class focuses on the preparation of fresh pasta and sauces (2 pastas and 2 sauces are prepared).
  • Lunch follows and everyone enjoys the food that was prepared in the cooking class.  Local wine included with each course, additional wine and beverages are available at a surcharge.
  • Afternoon free and on your own to stroll Montepulciano, stop for a glass of wine and tastings in our favorite enoteca, wine shop, or add on a wine tasting at Cinzia’s family vineyard in the countryside.  The family produces Vino Nobile wine.  Learn about the growing methods, harvest, pressing and bottling with tastings to follow.  If you would like to add on a wine tour, please let us know and we will send pricing for your group.

Day 3: Cooking Class 2 & San Biagio

  • Breakfast is served.
  • Tie on your apron for cooking class 2 for a Traditional Tuscan Menu. This hands-on cooking class includes the preparation of a full Tuscan Menu from appetiser to dessert.
  • Lunch follows on the foods prepared in class with local wine included, additional wine/beverages at a surcharge.
  • In the afternoon, stroll through Montepulciano and visit the Chiesa di San Biago.
  • Return to property, dinner on your own.

Day 4: Food Lover’s Walking Tour of Pienza

  • Breakfast is served.
  • Meet your driver and English- speaking guide for a half-day Food Lover’s Walking Tour of Pienza. The day includes a drive along winding country roads taking in the beauty of rolling vineyards, sunflower fields, and sleepy villages, until you arrive at Pienza.  
  • In Pienza, your English-speaking guide leads you through this charming town known for its artisan cheese with a visit to a family-owned cheese shop producing prized Pecorino aged in walnut leaves and grape must with tastings along the way. The tour continues to a butcher who produces traditional prosciutto, capocollo, lombo and finocchiona, a delicious Tuscan salami scented with fennel seeds.  We also visit an artisanal pottery atelier where you will see a local artist create beautiful hand-painted ceramics. While in Pienza, soak up the views over green fields that surrounds the town, shop at any of the quaint shops or sit in the piazza and enjoy a creamy gelato. 
  • Following your tour in Pienza, your driver will return you to the property.
  • Dinner on your own.

Day 5: Ciao Until Next Time!!!

  • Breakfast is served.
  • Check out & departure transfer.   Arrivederci!

Program Includes:

  • 5 days, 4 nights accommodations, based on 2 guests. Click to View!
  • Daily breakfast and maid service.
  • Welcome Dinner featuring a full course Chef’s Tasting Menu including an aperitivo – antipasto, pasta, main course and dessert with with a toast of local wine included. Additional wine and beverages available at a surcharge.
  • 2 hands-on cooking classes with lunch or dinner following including the food that was prepared in class. Local wine included, additional wines and beverages at a surcharge.
  • Half-day Pienza tour with English-speaking guide and driver.  Experience the Tuscan countryside while visiting Pienza and tasting your way through artisan food shops.  Tastings included.
  • Round trip transfers from Chiusi-Chianciano Train Station to Montepulciano.
  • Cooking Vacations welcome bag with chef’s apron, Prosecco toast, and recipe booklet.
  • A copy of Lauren’s cookbook, “It’s A Dream Place – Stories of Food, Love and the Amalfi Coast.”
Program Prices

$2,195 per person, based on 2 guests at the Garden Villa In Montepulciano.

$2,195 per person, based on 2 guests at the Deluxe B&B.

$2,595  per person, based on 2 guests at the Luxury B&B.

Arrival and Departure Transfers from/to Florence and other cities to Montepulciano can be added on at an additional fee.  Please call us for pricing.

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.

*Prices may vary in August.

Check Availability

2024 Dates: This program is available throughout the year. Check in and start your cooking program on any day of the week. Rates 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.