A Midsummer Night's Dream Montepulciano™

Tuscan Food & Wine Trails Tour ~ 5 Days

view tuscany tour

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, a Medieval Renaissance town set on a hill is in the region of Siena. The name of Montepulciano, according to legend, was founded by the Etruscans. Rolling Tuscan hills dotted with ever growing olive trees and fields of sunflowers is Tuscany. As you stroll through its cobblestone streets stop for a local wine, Vino Nobile, shop for artisan terracotta ceramics, and stop to see the view. Montepulciano sits on a hill protected in an ancient Medieval wall creating some of Italy’s most applauded wine and cuisine.

Montepulciano Accommodations

Luxury 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.


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.

Itinerary~ 4 Nights and 5 Days


Day 1: Arrival, Welcome Dinner & Wine Pairing

  • Arrival transfer to Montepulciano and check in.
  • Relax.  Review your itinerary and welcome bag.
  • In the evening, your Welcome dinner is served featuring a Chef’s tasting dinner paired with local wine included.  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:The Tuscan Food Trails Tour – Cheese, Wine & Landmarks

  • Breakfast is served.
  • Meet your driver and English- speaking guide for a delicious full day Food Trails Tour in the countryside of Montepulciano.  Visit a precious artisan cheese maker and farm or vineyard and wine producer (select one option).  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, visit a cheese farm or vineyard and winery – both tours includes tastings.  Learn the art of making Pecorino cheese and taste a variety of types. Or, if you’re a wine enthusiast, visit the Tuscan winery and cellar with a tasting of Vino Nobile.  *When you reserve, please let us know your selection.
  • Return to 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 chef’s full course 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.
  • Full day Tuscan Food Trails tour with English-speaking guide and driver.  Experience the Tuscan countryside while visiting Pienza and tasting your way through artisan food shops.  Landmark visits and artisan ceramic shop visit included.  Select either a vineyard tour and tasting or cheese maker and farm visit.
  • Round trip transfers from Chiusi-Chianciano Train station to Montepulciano.
  • Cooking Vacations welcome bag with chef’s apron, Prosecco toast, and recipe booklet.
Program Prices

$2,295 per person, based on 2 guests at the Luxury B&B.

$2,395 per person, based on 2 guests at the Luxury B&B in a superior room.

$1,995 per person, based on 2 guests at the Garden Villa In Montepulciano.

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.

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.