Retreats 2026

Massi and Jordana’s 2nd Annual Food and Wine Retreat in Tuscany

April 17 - 22, 2026

8-bedroom villa in the countryside of Siena

5 Essentials

1) Real Italian food: farm to table, and cooking classes with Chef Massi. Participation in cooking is welcome, and cooking classes will be organized for those interested.

2)Incredible Italian wine: Touch the soil where the grapes are grown and see how each family is unique in their wine-making approach and philosophy. Experience exclusive barrel tastings and discover the diversity of Italian terroir from the Chianti to Montalcino.

3)The joy of community: Forge new friendships and celebrate the spirit of togetherness. Dining together at a large table with Chef Massi’s cooking every night is definitely one of the big highlights. Enjoy group activities and excursions, creating memories that last a lifetime.

4)The peacefulness of slowing down: Embrace the Italian art of “La Dolce Vita” by taking time for yourself and your companions. Stroll arm in arm through medieval towns, soaking in centuries of history and charm. Unwind in the tranquil countryside, surrounded by olive groves and vineyards.

5)The boundless beauty of Tuscany: Immerse yourself in the natural splendor and timeless allure of the Tuscan landscape. Explore picturesque villages and hidden gems off the beaten path. Marvel at breathtaking sunsets over rolling hills and cypress-lined roads.

Where: Podere Antico Macchione. 8-bedroom villa in the countryside of Siena. We are 30 minutes north of Montalcino. 15 minutes south of the city of Siena. One hour away from Florence, and 2.5 hours away from Rome airport. Imagine Tuscan rolling hills, cypress and olive trees, sunset views from the outdoor dining patio, lavender fields, mythological animals (fox, porcupine, white owl, jackrabbit, and wild boar), and the vast night sky full of stars and the transforming phases of the moon.

Price: €9500 per couple/shared room. €6500 per single room. All rooms include a private bath. Early bird pricing until December 1st €8800 per shared room. €6000 per single room.

Itinerary and Highlights: We curate the specifics of the itinerary based on the final guests who join the trip to keep the schedule exciting, adventurous, and spectacular for everyone participating.

Friday, April 17th: Welcome aperitivo and dinner at the villa.

Saturday, April 18th: Morning yoga (optional). Massi’s amazing breakfast buffet. Chianti Day. Wine tasting and lunch at a historical and favorite winery. Visit Siena in the afternoon. Free time to go shopping and walk around. Aperitivo on the terrace of the villa. Special dinner at the communal table prepared by Chef Massi.

Sunday, April 19th: Morning yoga (optional). Breakfast Buffet. Late morning hike (optional). Sunday Italian lunch at the Villa. The Sunday lunch is one of our features. We will spend the whole day relaxing at the villa and enjoying a traditional Sunday Italian lunch. Of course ours will be a little more exciting. We will invite friends, winemakers, artisans, and local personalities to join us, about 30 people. Chef Massi will light up the BBQ, there will be lots of different wines to try, and never-ending food and laughter. When guests leave, we will start our own pizza party around 7pm on the outside terrace with the wood-burning pizza oven while watching the sunset and the oncoming moonlight and stars. You can make your own pizza with Massi and experience the joy of having nothing important to do other than just being in community.

Monday, April 20th: Morning yoga (optional). Breakfast buffet. Montalcino Day. Visit a favorite family-run winery in Montalcino and taste the famous Brunello di Montalcino. Lunch at a winery in Montalcino. Walking tour of Montalcino, followed by free time to explore. Dinner at the villa with a surprise blind tasting of top Italian producers.

Tuesday, April 21st: Morning yoga (optional). Breakfast buffet. Montalcino and Val d’Orcia. Winery in Montalcino. Lunch in the town on Montalcino. Visit a small historical town. Late afternoon cooking class with Massi at the villa (optional). Last night special wine dinner and surprise guests at the Villa.

Villa will be equipped with a classic cocktail bar (please let us know if you have any special requests). House wine will be a mix of our favorite Italian wines, including sparkling wine, rose, white, and red. All wines and cocktails are available as self-serve. You will not lack any wine.

Yoga will be available every morning with our favorite yoga teacher Cally Albrecht, who is also the owner of the villa. There is a professional yoga studio at the villa.