Full of green olive groves and manicured vineyards, the rolling hills of Tuscany are an unmistakable landscape. Perched atop one of these hills is Castello di Casole, a grand hotel housed in a 10th-century former castle. The best way to explore these famous views is on an equally famous ride — a Harley-Davidson motorcycle. Mount either an Electra Glide Ultra or a Road King and ride through the region’s winding roads, quaint villages and towns, including San Chimento, Monteriggioni and Croce Fiorentina (the specific route you take is up to you). For a totally immersive experience, choose to have an Italian opera soundtrack while you ride. Or, if you prefer, a co-driver can be added so you’re free to enjoy the ride.
Oliveto Suite from $1,500 per night, Harley-Davidson experience from $1,050 per person. Contact Federico Galligani, general manager, email@example.com, +39 0577 961 501, castellodicasole.com