Whether you prefer a relaxed ride past olive groves, a scenic journey through medieval villages, or a challenging climb into the hills, these three curated itineraries offer something for every rider.

Architecture, art, cuisine, traditional brick and stone cityscapes, and rich local culture – Siena is a veritable time capsule of medieval Tuscany. Its historic center has remained mostly untouched through the centuries, making the city a must-visit for Tuscan travelers.

Truffle hunting is more than a quest for a rare delicacy; it is an extraordinary opportunity to immerse yourself in history, culture, and natural beauty while experiencing the thrill of unearthing your own gastronomic gem.

Now transformed into a peaceful countryside escape, Casali di Casole’s meticulously restored Tuscan farmhouses are a testament to the enduring magnetism of the region that has kept historians, tourists, artists, and locals alike enraptured through the centuries.

Embarking on a day trip to San Gimignano is akin to stepping into a time machine, where cobblestone streets lead to centuries-old towers, and every winding path reveals a story.

Staying at Casali di Casole allows for you to have a unique Italian experience where you see the true beauty of Tuscany. Traveling from the estate around this beautiful region is easy and allows for you to discover amazing cities and towns.

Timbers Resorts has perfected the fine art of Private Residence Clubs by creating authentic experiences for Owners and guests to feel right at home.