CoolVINES in Italy // A WINE & Food exploration

November 2-9, 2019

explore / sip / cook / harvest / learn

CoolVines is a wine shop and gourmet market that inspires us every time we walk into one of their locations. This is because they source the very best food and wine made by real people, and they aim to personally connect themselves to the artisans whose food and wine they sell - and it shows. In the spirit of this approach, we are thrilled to collaborate with CoolVines to curate an immersive food and wine adventure as we explore the Tuscan countryside, meeting wine makers, food purveyors, farmers and artisans. Together, we'll wander ancient cities and small hamlets. We'll learn to make pasta and to cook with olive oil. We'll make our own pizza in a 1000 year old restored outdoor oven. We'll visit ancient thermal baths and have some time for yoga, and we'll immerse ourselves fully in the Tuscan experience.

Fall is one of the most exciting times of year to travel to Italy, when the olive harvest is underway and the air is buzzing with excitement. During our week together in Italy, we’ll harvest olives on an organic farm, then press them on site to make the highest quality extra virgin olive oil, and you'll learn that there's nothing quite like dipping bread in some freshly pressed olio!

The setting for this week will be the immaculately restored 11th century luxury agriturismo, Villa Montecastello, a working organic farm and olive grove, perched high atop a hillside with 360 degree views of the countryside. The villa has been immaculately renovated to offer its visitors an understated luxury experience in Tuscany centered around food and wine.

Located one hour south of Florence, the Villa is surrounded by olive groves, with vineyards and nature reserves at its base. With extensive vegetable and herb gardens, in-house raised animals and olive oil made on site, much of the produce that will be used in the meals and cooking classes throughout the week will come right from the farm, making for a truly unique and authentic farm to table cooking experience.

We invite you to join us and our friends from CoolVines this fall in Tuscany, in building deeper connections to ourselves and each-other, the wines that we drink and the food that we eat.


For more on CoolVines click here.


  • Saturday // Arrival to Villa Montecastello, light lunch upon arrival. Time to relax and unpack. Tour the grounds and explore the locations rich history, visit the vegetable gardens and meet the animals that live on-site. Sunset prosecco followed by a farm fresh welcome dinner at Villa Montecastello.

  • Sunday // Breakfast. Olive harvest! Harvest and press fresh olive oil - there is nothing quite like it! Lunch at Villa Montecastello. Afternoon olive oil focused cooking class, followed by a dinner of our own creation at Villa Montecastello.

  • Monday // Breakfast. Morning yoga class. All day trip to Florence to explore this amazing city on your own. Lunch and dinner out on your own. We'll provide transportation both ways, maps and advice on the best spots to eat, drink shop and explore.

  • Tuesday // Breakfast. Travel the rolling Tuscan hills to picturesque Montalcino to visit a boutique Brunello maker. After an intimate tour through the cellar we'll taste the wines made here. After we will travel to the nearby town of Bagno Vignoni, for lunch and time at the local thermal baths to experience the healing power of these ancient waters. Head back home for a casual evening and dinner at Villa Montecastello.

  • Wednesday // Breakfast. Morning trip to a local organic dairy outside of San Gimignano. We'll tour and have a cheese tasting. Quick stop for a stroll through the walled in town of San Gimignano before heading back to the villa. Evening dinner out on your own in old Colle Val d'Elsa, where you'll be dropped off and picked up after dinner.

  • Thursday // Breakfast. Morning yoga. Pasta class! Learn to make fresh pasta, then enjoy a lunch of your own creation. In the afternoon, we will travel to Siena to spend a few hours exploring on your own. Return to Villa Montecastello for grill night!

  • Friday // Breakfast. Morning trip to Chianti Classico town of Gaioli for a winery tour and tasting. Lunch together in the charming hamlet of Gaioli in Chianti. Head back to the villa. Farewell Dinner - Pizza Party night at Villa Montecastello with local artisanal beers - make your own pizza in our 1000-year-old outdoor oven with a local pizzaiolo!

  • Saturday // Breakfast and departure for airport.

The Details

Villa Montecastello will be your private Tuscan oasis during this week long retreat. We invite you to immerse yourself in the sights and sounds of nature, eat to your heart's content, and to sit by the fire with a glass of wine in hand.

This adventure will immerse you in the joys of Italian culture, and introduce you to new perspectives on food and wine, inspiring you for years to come. The experts from CoolVines will guide you during this hands-on week, sharing their own extensive knowledge on wine, and leading you through the simply amazing and flavorful experience of living a week in Tuscany to the fullest.

The week includes 7 overnight accommodations at Villa Montecastello, 7 breakfasts, 6 lunches, 5 dinners, all local transportation as described in the itinerary including airport pickup and drop off at Florence airport. Daily breakfast buffet includes locally baked goods and produce, fruit, coffee, tea and juice. Also included are all of the materials for cooking classes, wine tours and tastings. Unlimited bottled water (sparkling and flat) at the villa. House wine with lunch and dinners from our expertly curated house selection, plus all fine wines for tastings and winery tours. Gift bag of gourmet olive oil and vinegars curated by Villa Montecastello.

Not included in pricing: Airfare, all extra beverages, additional transportation outside of itinerary.

Each room at Villa Montecastello 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 and heat. 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, and a library filled with books about Italy, food and wine. It is the perfect home base for our trip.

For more on Villa Montecastello visit


  • Leccino Apartment // $6200 per person for double occupancy: Our largest most private accommodation, this one bedroom apartment has a large bedroom with king bed, living room with sleeper sofa, a beautiful kitchen and dining room, and an oversized bathroom, plus a private entrance and exclusive back patio. A true home away from home.

  • Frantoio Suite // $5900 per person for double occupancy, $6400 per person single occupancy: Our most romantic room, beautifully appointed with a King size canopy bed and en suite bathroom with claw foot tub.

  • Pendolino Studio // $5600 per person for double occupancy, $6100 per person for single occupancy: A charming studio with Queen bed, private en suite bathroom and kitchenette.

  • Foresteria Bedroom // $5600 per person for double occupancy, $6100 per person for single occupancy: A beautiful large bedroom with King bed or two Twin beds and private en suite bathroom.

  • Moraiolo Bedrooms #1 & #2 // $5300 per person for double occupancy, $5800 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 // $5000 per person for double occupancy, $5500 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.

    BOOKING TERMS: Booking directly with Villa Montecastello US office - 973.327.2336. 50% non-refundable deposit due to secure booking, 50% balance due 4 weeks before departure. Online bookings require full upfront payment, plus an additional 3% charge will be added for booking online. Payment can be made by credit card or check. 6 guest minimum required to run the trip.

For questions or to book direct email us or call 973.327.2336