I’ve long been obsessed with Italy — as a little girl my grandmother would share picture diaries of her travels, and Italy’s entice always felt the most romantic and sophisticated of all the European gems. Any Italy-obsessed traveler will tell you there’s plenty of ways this small country lives up to, and surpasses, the hype. And if there’s one city to continually flirt with, it’s Tuscany. I’ve been fortunate enough to walk the property of the Casali di Casole pre-development, before 32 individual homes graced its undulating hills, olive groves, and gorgeous terraced vineyards. Even then there was something majestic about the land. Today, as the largest privately held property in Italy, it consistently tops nearly every award list and property ranking. Why? The reasons are manifold — and there’s no better time to make the trip. Here are the Top 5 reasons to go — and now!
This was, hands down, my most memorable Italian affair. And you don’t need to leave the estate for this bucket-list adventure. During the fall — or truffle hunting season — your Concierge can arrange for a day of exploring the private reserves with an expert guide and truffle hunting dogs from the Lagotto Romagnolo breed. Afterward, visit local osterias for a celebratory truffle-infused meal or enjoy lunch at your Club villa prepared with your bounty and paired with local Tuscan wines.
Whether you bike or drive through Tuscany’s famous vineyards be prepared for storybook wow factor. Oenophiles continually return to this wine region for good reason: small vineyards, approachable winemakers, and oh-so-tasty vino. Any trip to Tuscany calls for a day (or two or three) of wine tasting. Chianti, Brunello di Montalcino, and Fruili? Yes, please! Plus, Casali di Casole is surrounded by more than 100 acres of vineyards. Your concierge team can arrange in-residence private wine tastings, expertly paired dinners with a sommelier, and winery tours.
Get Your Adventure On
Whether a biker, horseback rider, or golfer, Casali di Casole can host all three. Mountain bikers can tackle trails through enchanting terrain right on the estate or visit the nearby biking hub of Monteriggioni. If you’re more inclined to adventure by horse, a top-notch equestrian center is located just 35 minutes from Casali di Casole, offering both trail rides and horseback tours. And if tee time is calling, golfers can access three quintessentially Italian (less manicured, rolling terrain) courses, all located a short drive away.
Explore Neighboring Villages
Casali di Casole is ideally located close to charming Tuscan destinations. Siena is just 50 minutes east; Florence 1 hour and 15 minutes north. The coast is only a scenic 1.5-hour drive. Volterra (known for medieval frescos and statues) and Montalcino (situated in the amazing Val d'Orcia Natural Park) are short day trips, too. And don’t miss the walled fortress of Monteriggioni — best explored via an unforgettable day of cycling. The estate’s closest neighbors? The hilltop towns of Mensano, Radicondoli, and Casole d’Elsa (the property’s namesake). You’ll also be able to spy the iconic 13-century towers of San Gimignano from the property.
Witness the Leaning Tower of Pisa
A must-see. Yes, it’s tourist-y. But there’s reason to make the short day trip from your Club headquarters to marvel at this construction. Started in 1773, the Leaning Tower of Pisa took nearly 200 years to complete. Though the incline of the famous bell tower wasn’t intentional, it became the building’s calling card. A historical landmark, the tower has been used by a famous cast, from Galileo Galilei to the Nazis — as an observation post during WWII.
Where You Will Stay
Tuscany is our Members' #1 bucket list destination with a close proximity to local wine and freshly made pasta, the art of nearby Florence (think Michelangelo's David), and medieval towns like San Gimignano. After a day of exploration, catch the sunset over the countryside's rolling hills. Our four-bedroom luxury villas offer serenity on a remote estate set among acres of olive groves and vineyards. The five residences at Casali di Casole, feature a classic Italian kitchen and a traditional forno for baking pizza.