Discover Montalcino and More in Tuscany

Arrive in Montalcino. This would be a great day to explore the property you’re staying at, stroll the town, grab gelato at Gelateria Artigianale Why Not? Get familiar with the area. Additionally, there are many locally owned, artisanal shops to visit. If you arrive in time, grab a seat outside and enjoy the sunset and aperitivo from Caffe’ La Fortezza.

For dinner, enjoy traditional tuscan fare at Taverna del Grappolo Blu. Included in the Michelin guide. I stop here each time I return to Montalcino, and to this day, think about my first meal here eight years ago.

Want to immerse yourself in the rolling tuscan hills? Biking through this region is a bucket list item for many. A bike tour can be arranged to explore a UNESCO World Heritage Site, Val d’Orcia, and more medieval villages. I recommend starting in Montalcino and head to Castiglione d’Orcia, make way through Bagno Vignoni (known for its thermal hot springs) and end in the charming town of Pienza.

Explore the town of Pienza and enjoy dinner at an osteria.

Explore a few of the 250 wineries producing Brunello di Montalcino in the region. From biodynamic wineries to more traditional methods, there is something for everyone. The wine tour will begin mid-morning with pick up at your hotel. From there, grab lunch at Il Pozzo in Sant'Angelo in Colle. After lunch, visit one or two more wineries during the afternoon. If you’re interested in olive oil tastings, several of the wineries also produce olive oil and can be included with you tour. If time permits, I recommend visiting the Abbey of Sant’Antimo and catch a vesper service performed each day by the monks.

After working with many local tour operators, I have several contacts that deliver an exceptional experience. I’ve also visited over 20 vineyards in the area, and am happy to share my favorites.

Enjoy innovative Tuscan cuisine at Locanda e Drogheria Franci, a restaurant inspired by flavors near and far. The menu changes frequently.

Enjoy an organic farm-to-table cooking class Interested in learning how to cooking traditional tuscan dishes? Visit Locanda Demetra where you will learn to make a multi-course lunch. This establishment was created by five entrepreneurs in the Montalcino area, where an abandoned farm house was given new life. They will start the cooking class with a tour of their garden and walk you through the ingredients you’ll be using. Each class will include starters, home made fresh pasta, a main course paired with a side dish and a dessert. Sound intimidating? Alessandro and his team make this experience fun, educational, and easy. After preparing the menu, all participants get to enjoy each dish, family style, in an al fresco setting.

No interest in cooking? You can still eat at Locanda Demetra as their farmhouse operates as an intimate restaurant, with about 10 tables. Reservations are necessary. 
Celebrate your last night spent in this beautiful part of the world at Boccon DiVino. Modern, tuscan cuisine served alongside views of Tuscan countryside. Another local establishment featured in the Michelin guide.