“I’m so excited to be immersed in the beautiful countryside of Tuscany with my guests as we experience new flavor pairings together and experiment candidly with every dish! Guests can expect hands-on classes that start from the source - estate-grown produce, meats, dairy; local fish, honey, wine - and develop into theory and technique driven classes that will enable everyone to replicate these foods at home without following a recipe. We’ll be covering everything from miso cavatelli to smoked bone marrow ice cream, with plenty of cocktail classes in-between - come join us!”
— Jenny Dorsey
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Wednesdays in Tuscany with Chef Jenny Dorsey

OCTOBER 13-20, 2018



At this pop-up cooking school, Jenny will lead a group of curious travelers on a journey to discover the best local ingredients, and then head back to the kitchen to teach students how to best use these ingredients to make the most delicious meals, exploring together the different ways to highlight their most unique qualities.  Jenny will challenge students to think outside the box, and to be inspired by their environment and creative instincts when working in the kitchen. Cooking classes will be complimented by mixology lessons, incorporating local liquors into tasty cocktails that pair beautifully with meals, as well as adventurous day trips exploring the best of Tuscany.

Jenny Dorsey is a professional chef and artist based in New York City, who makes food to express
the full range of human emotions, and believes the dinner table is a powerful medium for
storytelling and creates a place for genuine interaction. She is a chef who wants to change the
world with her art, one honest conversation at a time.  Jenny is the founder of Wednesdays, a popular experimental popup dinner series combining fine dining with engaging conversation. Wednesdays has been named as one of the best NYC and SF dining experiences by Business Insider, 7x7 and UrbanDaddy and featured in publications such as Epoch Times, The Huffington Post, Village Voice, Eater, Thrillist, and more.  Jenny is also co-host of the Why Food? podcast on Heritage Radio Network.

The setting for the retreat will be the 1000 year old exclusive estate, Villa Montecastello, a working organic farm and olive orchard that has been immaculately renovated to offer its visitors an authentic and understated luxury experience in Tuscany.  Located one hour south of Florence, the Villa is surrounded by olive groves, with vineyards and nature reserves at its base.   Villa Montecastello is a full size working organic farm, producing award winning extra virgin olive oil, as well as a unique and vast assortment of garden produce which will be used in your meals and cooking classes throughout the week.  The villa is home to an array of farm animals including the local breed of Cinta Senesi pig, donkeys, chicken and guinea fowl.  Your week spent in this storybook setting will be complemented by clean farm to table eating, magical day trips to ancient local towns and hamlets, and visits to boutique vineyards of Tuscany led by a private guide and wine expert.


  • Saturday: Arrival to Villa Montecastello.  Light lunch and time to relax and freshen up.  Tour the grounds, vegetable gardens and meet the farm animals. Sunset aperitifs + welcome dinner at Villa Montecastello.
  • Sunday: Breakfast. Visit to the local  our mill + the chicken coop at Villa Montecastello. Learn to make a few varieties of fresh pasta then enjoy them for lunch.  Afternoon cheese tour + tasting.  Dinner together at local trattoria.
  • Monday: Breakfast. Morning trip to Montalcino for a winery tour + Brunello tasting. Lunch at a restaurant in Montalcino. Back to the villa for a late afternoon class: Wood  red goodness! Pizza and roast chicken in the 1000 year old outdoor oven, followed by dinner at Villa Montecastello.
  • Tuesday: Breakfast. Olive tour + harvesting + tasting.  Mixology class: why Italian amaros are a mixologist’s secret ingredient. Plus how to pair  seasonal cocktails with Italian cheeses. Light lunch with cocktails. Free time. Fish dinner at Villa Montecastello.
  • Wednesday: Breakfast. All day trip to Florence! Lunch and dinner out on your own.
  • Thursday: Breakfast. Market visit + market mystery basket cooking class. Lunch of everyone’s own creation. Afternoon departure for Chianti for a tour + tasting at a boutique winery.  Dinner out in Chianti. 
  • Friday: Breakfast. Honey tour + tasting. Pastry class: Cakes and ice cream with honey.  Light lunch and free time.  Afternoon mixology class: Advanced mixology techniques, simplified. Dinner is grill night with a whole suckling pig!
  • Saturday: Breakfast. Depart for airport.

all inclusive accommodations

The week includes all overnight accommodations at Villa Montecastello, 7 breakfasts, 6 lunches, 6 dinners, welcome prosecco reception, house curated wine selection with lunch and dinner, private class instruction and all tools needed to participate in cooking classes, excursions, all local transportation as described in the itinerary, airport pickup and drop off at Florence airport only.  Daily breakfast buffet includes locally baked goods and produce, coffee, tea and juice.  Special breakfast items available upon request.   

Not Included in Pricing: Airfare, extra beverages outside of meals, transportation or activities outside of itinerary.  On site massage available for booking.

Each room is uniquely furnished with the utmost attention to detail.  All rooms offer luxury hand ironed linens,  hand made olive oil soap and shampoo, fresh cut flowers and air conditioning.  Villa Montecastello offers 8 room options of varying sizes and pricing, each is filled with beautiful antiques,  warmth and charm.  The Villa Montecastello has many shared sitting areas both inside and out, a library filled with books about Italy, food and wine, as well as a professional chef’s kitchen where your cooking classes will take place.


  • Leccino Luxury Suite: $6200 per person for double occupancy - The largest apartment offering the most comfort and space with one bedroom with Queen bed, a private living room with pull out sofa bed,  replace, living room area, kitchen and large ensuite bathroom
  • Frantoio Suite: $5800 per person for double occupancy - Our most romantic room, beautifully appointed with a King size canopy bed and ensuite bathroom with claw foot tub
  • Pendolino Studio: $5500 per person for double occupancy, $6000 per person for single occupancy - A charming studio with Queen bed, private ensuite bathroom and kitchenette
  • Foresteria Bedroom: $5500 per person for double occupancy, $6000 per person for single occupancy - A beautiful large bedroom with King bed or two Twin beds and private ensuite bathroom
  • Moraiolo Bedrooms #1 & #2: $5200 per person for double occupancy, $5700 per person for single occupancy - Cozy and lovely rooms with private bathrooms across the hallway, just a few steps outside the room.  Bedroom #1 has the option for a King bed or two Twin beds.  Bedroom #2 has a Queen bed.
  • Frantoio Bedrooms #1 & #2: $4900 per person for double occupancy, $5400 per person for single occupancy  - Well appointed and roomy bedrooms share an extra-large bathroom with separate room for shower and toilet for additional privacy.  Bedroom #1 has a Queen Bed and Bedroom #2 offers the option of King or two Twin beds.

Click for more about Jenny Dorsey.

*Note for online bookings a booking fee of 3% is included in the pricing.
For questions or to book direct email us or call 973.327.2336