Tuscany is wonderfully multifaceted. One moment, you’re immersed in the peace of rolling hills and vineyards; the next, you’re strolling through museums or vibrant piazzas (city squares). Add in pristine coastlines and charming hilltop towns, and you’ve got a region bursting with variety. With so much to see and experience, we want to share with you a spot that puts it all within reach. Meet Casole d’Elsa, a charming town situated in the heart of the Val d’Elsa region: it’s a place where you can bounce from vibrant city adventures to relaxing Italian countryside without missing a beat. Enjoy the best of both worlds, all in one.

Casole d’Elsa: Your Perfect Base in Val d’Elsa

Rolling hills of lined cypress trees, perfectly landscaped vineyards, and lush olive groves—the commune of Casole d’Elsa embodies the quintessential Tuscan experience. Far less crowded than more famed corners of Italy, this part of the Val d’Elsa region offers a tranquil alternative, without sacrificing the scenic beauty that defines Tuscany.

Ancient Roots

The area around Casole d’Elsa has roots that stretch back to the Etruscans, one of Italy’s pre-Roman civilizations. Archaeological discoveries have revealed tombs and artifacts, indicating that the town’s history long predates the medieval era that shaped much of its current landscape. Its historic center, perched on a hill and capped by a fortress, surely makes you feel like a time traveler. Wander through quiet, cobblestone streets where family-run trattorias serve recipes passed down through generations. Be bewitched by intricate frescoes in tiny chapels and linger in sunny piazzas to sip a glass of locally produced wine. Here, history isn’t confined to just museums, it’s lived in every season, harvest, and daily tradition.

The Ultimate Base for Exploring Tuscany

One of Casole d’Elsa’s greatest charms is its exceptional location. Perfectly situated between Florence and Siena, you can easily fill your days with art, history, and gastronomy.

Florence and Siena

In under an hour’s drive, you can find yourself in Florence, a cultural treasure trove. Marvel at Renaissance masterpieces in the Uffizi Gallery, climb Brunelleschi’s dome for sweeping city views, or browse leather goods and artisanal crafts at Mercato Centrale. Maybe you can finally visit the Vasari Corridor, set to reopen by the end of 2024 after almost a decade-long renovation. (Be sure to check out our post about touring Florence.)

Equally close, and only about 35 minutes away, lies Siena, a UNESCO World Heritage Site. Many of its iconic landmarks, including the Romanesque Gothic Duomo and the historic Piazza del Campo, date back to the 12th century, and today the city still captivates with renowned artworks by Donatello, Bernini, and Michelangelo, as well as the fierce Palio horse race each summer.

Tucked within easy reach of Casole d’Elsa lie a trio of enchanting hilltowns, each with its own story to tell. Whether you’re drawn to ancient Etruscan lore, vampire folklore, or medieval intrigue, these nearby gems promise delightful excursions near your base.

Charming Towns in the Immediate Vicinity

• San Gimignano: Known as the “Manhattan of the Middle Ages,” its distinctive skyline of soaring towers once proclaimed the wealth and power of the families who built them. As you are strolling through the streets, don’t forget to have a gelato at the two-time world gelato champion, Gelateria Dondoli, in the central piazza.
• Volterra: Before the Romans arrived, and long before Stephanie Meyer’s “Twilight” series placed it on the vampire map, Volterra flourished under the sophisticated influence of the Etruscans. Today, while history buffs explore the Guarnacci Etruscan Museum and the town’s alabaster workshops, fans of the supernatural can revel in the lore of the Volturi—an ancient vampire coven rumored to call this storied town home.
• Monteriggioni: If you are traveling with children, they might be pleasantly excited to visit this town. Monteriggioni served as a setting in the popular action-adventure video games Assassin’s Creed II and Assassin’s Creed Brotherhood. Surrounded by perfectly preserved fortress walls, this town transports you directly into the past. Climb the ramparts for sweeping countryside views, and wander through the quiet streets to feel the hustle and bustle this town once captured along medieval trade routes.

Coast

Not in the mood for city life? Go westward and meet the Tuscan coast. Within an hour’s drive from Casole d’Elsa, you can find golden beaches, fresh seafood, and coastal towns like Cecina and Castiglione della Pescaia. While Cecina’s family-friendly shores offer an array of beach clubs and casual eateries perfect for a laid-back afternoon, Castiglione della Pescaia blends medieval charm with coastal allure, its historic fortress perched above a picturesque harbor, fortified castles, villas, and impressive churches built by noble families over the centuries.

Montagnola Senese: A Haven for Active Tourism

If you’re into active tourism, to the east of Casole d’Elsa lies the Montagnola Senese, a hilly and richly forested region that is perfect for outdoor adventures and authentic Tuscan traditions. It will feel like stepping into a wilder side of Tuscany. Here, dense woodlands and hidden groves form ideal terrain for truffle hunting. The landscape of the Montagnola Senese, crisscrossed by trails, is perfect for hiking, mountain biking, horseback riding, and scenic walks shaded by towering chestnut and oak trees.

The landscape’s spectacular beauty also made it a coveted hideaway for aristocracy and nobles over the centuries, who built some of Tuscany’s most impressive villas. Among them is Villa Cetinale, a backdrop for numerous recent publicized weddings and also an addition to our Tuscandream collection.

Where to Stay in Casole d’Elsa

Have you fallen in love with Casole d’Elsa’s location yet? Within the exclusive grounds of the historic Casali di Casole estate, we want to introduce three meticulously restored villas—Le Macie, Campo al Doccio, and Casale Gabbro. These former farmhouses have been masterfully renovated to capture the quintessential Tuscan architecture. Terracotta roofs, rustic stone facades, and vine-draped pergolas echoes the region’s allure. Inside, guests are greeted with contemporary comforts: gourmet kitchens, spa-like bathrooms, and elegantly designed living spaces that offer panoramic views of the Val d’Elsa landscape. Each villa is a harmonious blend of old-world Tuscan charm and modern luxury, providing an unparalleled retreat for families.

Set within 4,200 acres of private land, it feels like your own little oasis. You can stroll through the verdant land in complete privacy, lounge by a private pool, or dine al fresco in the gardens—all without a hint of interruption. And when you’re ready to explore, you’ll find a variety of excursions for every interest just a short distance away.

When you reserve one of our villas, you gain access to local experts from our team who can tailor your stay to your exact interests—be it arranging a private pasta-making class, securing a truffle hunting guide in Montagnola Senese, or helping you skip the line at the Vasari Corridor (when it finally opens its doors again!). We are here to ensure that your time in Casole d’Elsa, and the larger Val d’Elsa region, is authentic, hassle-free, and unforgettable.