Overview Tuscany is widely celebrated for its vast vineyards and wineries, but the region offers a variety of experiences that go beyond wine-tasting. For those who aren’t as interested in visiting wineries, there’s an abundance of castles, charming towns, and villages to explore as you drive through breathtaking landscapes and scenic countryside. This area is renowned for being the backdrop of many iconic films, such as “Under the Tuscan Sun.” Embark on this journey, and you’ll feel as if you’re blending in with the locals while visiting some of the most intriguing places in Tuscany. Our two suggested routes are perfect for families. One route takes you through the beautiful Chianti Valley, including a visit to Val D’ Elsa, which is close to San Gimignano. The other explores Val D’ Orcia, home to Pienza and Montepulciano. Regardless of your choice, you’ll find yourself surrounded by awe-inspiring nature, including endless olive groves and vineyards that create the classic Tuscan hilltop scenery. These scenic routes combine main roads and winding hilltop lanes, allowing you to enjoy Tuscany’s countryside to the fullest. Suggested Routes and Villages:

#1: Exploring Chianti and Val D’ Elsa
If you wish to explore the picturesque villages located to the north of Siena, San Gimignano, a UNESCO World Heritage site, should be on top of your list. Take the Via Francigena, the ancient pilgrimage road connecting to Rome. This route will take you from Porta San Giovanni to Porta San Matteo, which are two ancient gates of the town. As you wander through San Gimignano, you’ll pass through the impressive Piazza della Cisterna, a grand square encircled by the Palace of the Podestà and the Salvucci Towers, as well as the Duomo Square. One of the town’s highlights is its famous gelaterias, which are known to serve some of the best gelato in the world. For those interested in history, be sure to visit the San Gimignano 1300 Museum, a family-friendly space that brings the medieval city to life.

Close to San Gimignano, you’ll find the Archeodromo in Poggibonsi, an archaeological excavation site that spans three historical periods. This site also features a lovely park area that’s perfect for a picnic. While you can explore the park and the excavation sites at any time, the living museum is open on Sundays.

For a more adventurous family activity, visit the Rocca di Staggia, a medieval fortress offering a fun, fantasy-inspired experience. After exploring the castle, take a stroll through the quaint and peaceful town of Sense Staggia, where you’ll find shops and restaurants that remain open daily from 10 AM to 7 PM.

Another stop along the route is the medieval fortress of Monteriggioni. This well-preserved town is perched atop a hill, with intact castle walls surrounding it. It’s a great place to enjoy panoramic views, have a coffee, and wander through the charming porticos and piazzas before continuing your journey toward the Chianti Valley.

#2: Exploring Montepulciano and Villages
If you’d prefer to head south from Siena, start your adventure in Montalcino. From here, take the slightly longer S2 route, which spans 27 miles (43 kilometers) and includes the famous Sant’ Antimo Abbey in Val d’Orcia National Park. This historic Benedictine abbey, nestled in a peaceful, picturesque setting, is often overlooked by tourists but is one of Tuscany’s hidden treasures. Nearby, you can explore the Giardino di Daniel Spoerri in Seggiano, a wonderful spot for a leisurely picnic.

Pienza is a cozy, charming town known for its production of Pecorino cheese. Once you arrive, take a walk into the village center and visit the stunning Piazza Duomo, where you’ll find the impressive Piccolomini Palace. Don’t miss the opportunity to stroll along Corso Rossellino, the main street named after the Florentine architect who designed many of Pienza’s most notable buildings. Pienza is also a great place to slow down and savor the rural lifestyle with a cup of coffee at a local cafe, where you’ll often find Pecorino cheese and extra virgin olive oil featured prominently on the menu.

For a fun and educational experience, head to the renowned cheese-making region near Pienza, Cugusi. You can visit Cugusi Dairy to stock up on locally-produced Pecorino cheese while learning about the cheese-making process, including a chance to meet the animals involved. If you’d like to enjoy a slower-paced afternoon, visit Podere Il Casale, a local farm where you can relax, enjoy a picnic, and observe the farm animals in a tranquil setting.

A visit to the gardens of La Foce is another excellent way to spend an afternoon. After your tour of the gardens, head to Dopolavoro La Foce for a relaxed dinner. This full-service restaurant offers an inviting beer garden with hammocks, ping pong tables, and plenty of open space for a casual evening outdoors.

Montepulciano, renowned for its wine, is the perfect destination for wine enthusiasts. Take a walk through the charming streets, and don’t miss the opportunity to enjoy a delicious lunch paired with Vino Nobile di Montepulciano. Family-friendly wineries in the area, such as Palazzo Vecchio and Il Loggio in Cortona, are perfect for a fun and educational visit.

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