This isn’t a typical cycling holiday. Tuscany 400 is a small-group, performance-minded ride designed for people who want more than just sightseeing. Over five days you’ll cover about 400 km and 5,568 m of climbing on three very different loop routes—Pantani’s training climb and the tufa-stone hill towns, the high passes above Montalcino, and the coastal roads of Monte Argentario. We stay in one hill-top farmhouse hotel near Scansano, so there’s no daily packing: ride out each morning, roll back each afternoon to your own serviced apartment, fresh kit from the laundry, and a recovery massage. With support vans, a pro mechanic, chef-prepared meals, and only 10 riders, the trip blends effort and comfort in equal measure. Whether you’re chasing a new benchmark or just want a memorable challenge in rural Tuscany, this is your ride.