moderate
3–5 hours per day
Moderately fit riders comfortable with uphill cycling and long days
Experience Tuscany’s rolling hills by bike while savoring wine tastings and cooking classes at a historic vineyard farmhouse. Discover why this cultural cycling retreat is a standout in outdoor travel.
October 18-25, 2025 • Activity Level 2 • Yoga, Cycle, Hike, Culinary
Experience the enchanting beauty of Tuscany on this immersive retreat. Explore medieval Siena and vibrant Florence while staying in a charming 15th-century farmhouse surrounded by vineyards. Enjoy cooking classes, wine tastings, daily yoga, and cycling through picturesque landscapes, creating unforgettable memories in this idyllic Italian setting.
During this retreat, we’ll embark on a journey through the lush rolling hill towns of Tuscany, immersing ourselves in the timeless beauty of the region. Our exploration will lead us to the medieval city of Siena and Tuscany’s vibrant capital, Florence. Throughout our stay, we’ll reside in a charming mid-15th-century farmhouse nestled within its own vineyard, just outside the picturesque medieval village of San Gimignano. The enchanting setting of this farmhouse, surrounded by vineyards and overlooking the Tuscan countryside, promises to be an experience you’ll forever cherish.
Carry plenty of water, especially on warmer days, as Tuscan hills can be deceptively demanding.
Smooth but sometimes uneven roads mean comfort is key for enjoying long rides through the countryside.
Popular classes fill quickly; book ahead to secure your spot and enjoy hands-on Tuscan cuisine preparation.
Tuscany’s sun can be strong during midday rides; protect skin and eyes to stay comfortable.
Tuscany’s vineyards trace back to Etruscan civilization, and Siena’s historic center is a UNESCO World Heritage site.
The retreat supports sustainable farming practices and encourages low-impact cycling to preserve the landscape.
Reliable bike suited for mixed paved and gravel roads typical of Tuscany.
spring specific
Enhances comfort during extended rides over varied terrain.
Spring showers are possible; stay dry without overheating.
spring specific
Keeps you hydrated throughout cycling and vineyard tours.