Best things to do in Gaiole in Chianti

Tour the vineyards, grounds, and castle at Castello di Brolio. The castle passed into the hands of the Ricasoli family in 1141, and still shows damage from bullets and cannonballs. Admire the surrounding rolling hills and 230 hectares (568 acres) of vineyards from the ramparts of the castle. Sample the family vineyard’s own Chianti wine--the formula for Chianti was invented here in 1872--over a three-course meal in the terrace restaurant.

Take a tour of Castello di Verrazzano, a historic vineyard known for its Chianti. On the grounds of a hilltop castle, you can explore the cellars, walk through the gardens and woodlands, admire the views, learn about the history of the vineyard, and sample some wine. You also can enjoy some olive oil, balsamic vinegar, and almond cookies. Some tour packages include a full lunch or dinner.

A former Benedictine monastery with a Carolingian edifice, Abbazia di Sant'Antimo offers archaeological intrigue. While there is no proof Charlemagne founded the site, the early foundations date back to his era. The abbey's humble interior houses Carolingian-era carvings depicting animals and plants. You'll see the inspiration for these works of art right outside the chapel doors, where vineyards, mountains, and landscaped gardens invite you to explore.

Established as a World Heritage Site, Val d'Orcia has inspired both Renaissance paintings and modern-day photographs with its flat chalk plains and fortified settlements. The breathtaking agricultural valley is dotted with villages such as Pienza, as well as vineyards that produce prestigious Italian wines. You can experience the area by hiking or driving. Consider finding a tour that offers a sunset package.

Enjoy the beautiful and well-kept red-brick buildings of Abbazia di Monte Oliveto Maggiore, a Benedictine monastery atop a scenic Tuscan hill. In the great cloister, view the frescoes painted by Luca Signorelli and Il Sodoma detailing the life of St. Benedict. Visit the monastery’s pharmacy to buy natural and ancient medicines. Stop into the tasting room to sample the monastery’s wines, grappa, and olive oil. Attend a mass to hear the monks performing a Gregorian chant.