A Midsummer Night's Dream Montepulciano™

Tuscan Food & Wine Trails Tour ~ 3 or 4 Day

Step along the cobblestone walkway in the Medieval walled city and step into a chic di luxe B&B dating back to the 14th century with 4 exclusive suites overlooking the Val D’Orcia in a cooking weekend of great Tuscan cuisine.

Our cooking program with Chef Massimo invites you into his kitchen for Tuscan cooking featuring the local food & wine of Montepulciano.

Tuscan Cooking

Step into our Tuscan kitchen and get ready for exquisite cooking with Chef Massimo. Learn about the history & method of cooking regional foods of Montepulciano and the surrounding Tuscany area.

Menus vary according to the season, with classics such as slow cooked Pici with ragù, hand-crafted ravioli stuffed with a walnut sauce, tagliatelle with Porcini mushrooms, bistecca di chianina,steak Florentine, artichokes & garden red tomatoes stuffed with delicate cheese & herbs, Chianti Etruscan sauce and beans all’uccelletta. There is always a sweet dessert and this time you will learn how to make classic cantuccini– biscotti always dipped in Vin Santo. Also on the dessert tray is Schiacciata con l’Uva, or Chianti wine biscotti. After class, lunch or dinner follows with the foods prepared in class.

Cooking classes start at 9:30am and last approximately two hours. After class, everyone eats the foods prepared in class together.  Local wine included.


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 was recently featured in the Twilight saga film ‘New Moon.’

Montepulciano Accommodations

Settle into your di luxe room, decorated with antique furnishings and breathtaking views of the two valleys and the lakes of Trasimeno, Chiusi and Montepulciano to set the mood. Each large private room has an en-suite bathroom stocked with linens and bath towels for your comfort. Luxurious furnishings adorn each of the 4 suites, just steps away from the Piazza Grande in the heart of Montepulciano.

Itinerary~ 3 Days, 2 Nights or 4 Days 3 Nights


Day 1: Arrival & Welcome Dinner & Wine Pairing

  • Arrival transfer to Montepulciano and check in.
  • In the evening, enjoy a welcome aperitivo at Massimo’s trattoria and your Chef’s Tasting Welcome Dinner paired with local wine included, additional wine/beverages at a surcharge.

Day 2: Cooking Class 1 & Montepulciano

  • Breakfast is served.
  • Meet in the kitchen for your 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 on the foods prepared in class.  Local wine included with each course, additional wine/beverages at a surcharge.
  • Afternoon free and on your own to stroll Montepulciano, stop for a glass of wine & tastings in a local shop, or ask about reserving a wine tasting at Cinzia’s family vineyard. Their prized Vino Nobile wines will delight any palate and Wine Spectator agrees, with a rating of 91 for their Vino Nobile di Montepulciano 2006.  You may also add on the Tuscan Cheese, Bread & Wine Tour

Day 3: Cooking Class 2 & Departure

  • Breakfast is served.
  • Meet in the kitchen for your Cooking Class 2 for a Traditional 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.
  • Check out & departure transfer after lunch.   Arrivederci!
  • Or Add On Another Day

Day 4:The Tuscan Food Trails Tour – Cheese, Wine & Landmarks

  • Breakfast is served.
  • Enjoy a delicious Food Trails Tour with English-speaking guide with private transportation included.
  • The half day Tuscan Food Trails tour takes you to the finest makers of artisan cheese or wine in the Montepulciano region with an English-speaking guide and private driver. Follow the winding roads with Serena, and discover the delicious foods of Tuscany, while taking in the beauty of rolling vineyards, green hills, and villages along the way.You will learn the process and how the artisan makers continue to create by hand beautiful cheese, wine and local products. Start off in the center of Montepulciano and make a quick stop at the temple of San Biagio, one of the town’s highlights. Then drive to Pienza where a guided walking tour of the village will treat you to wonderful views over the nearby Tuscan hills and take you along ancient streets lined with shops and artisan workshops. We stop off for a cheese tasting in a family-owned cheesemaker’s and marvel at the incredible array of cheeses on offer: pecorino matured in walnut leaves, chestnut leaves, or in grape must, and those matured in specially-created pits. Then, further on, stop off to sample local prosciutto, capocollo, lombo and finocchiona, a delicious Tuscan salami scented with fennel seeds. Visit the artisanal pottery atelier where you will meet a local artist and watch how she transforms clay into beautiful hand-painted ceramics. Cheese lovers will visit a farm to see how local pecorino cheese is made, and taste a variety of different types of pecorino made on the premises.  Or, if you’re a wine enthusiast, on the other hand, drive to a local winery and visit the cellar – tasting of Vino Nobile is included. (*When you reserve, please let us know if you prefer to visit the artisan cheese farm or the beautiful winery.)

Day 5: Ciao Until Next Time!!!

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

Program Includes:

  • 3 days, 2 nights accommodations, based on double occupancy in a private accommodation with ensuite private bath. Click to View!
  • Daily breakfast and maid service.
  • Chef’s Tasting Welcome Dinner with aperitivo and local wine included. Additional wine/beverages at a surcharge.
  • 2 hands-on cooking classes with lunch or dinner following on the foods prepared in class. Local wine included, additional wines/beverages at a surcharge.
  • Round trip transfers from Chiusi-Chianciano Train station to Montepulciano.
  • Or Add On an extra night and Food Trails Tour with English-speaking guide and driver.
Program Prices

Luxury B&B

$1,495 per person, based on 2 guests for the 2 night tour.
$1,695 per person, based on 2 guests for the 3 night tour with full day Tuscan Food Trails tour.

Luxury Apartment

$1,295 per person, based on 2 guests for the 2 night tour.
$1,495 per person, based on 2 guests for the 3 night tour with full day Tuscan Food Trails tour.  Breakfast not included.

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.

*An Italian visitor tax may apply in some cities and must be paid directly on site at check out.

Check Availability

2021 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.