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A visit to Tuscany is a trip into the country. There are plenty of good hotels in the larger towns, but the classic experience is to stay in one of the rural accommodations—often converted private homes, sometimes working farms or vineyards (known as agriturismi).
Though it's tempting to think you can stumble upon a little out-of-the-way hotel at the end of the day, you're better off not testing your luck. Make reservations before you go. If you don't have a reservation, you may be able to get help finding a room from the local tourist office.
People come from all over the world to enjoy the quiet country life in this 16th-century farmhouse, where rooms are furnished with unadorned wooden furniture. Dinners, which are included in rates along with breakfast, are inventive. The friendly owner, who speaks English, enjoys serving local dishes and wine while sparking conversation at the dinner table.
In what was originally an olive oil mill, this boutique property has sweeping views of Montepulciano and Monte Amiata and rooms inspired by a traditional Tuscan aesthetic, with elements such as herringbone terra-cotta floors and patterned satin linens. The restaurant is headed by Tuscan chef and cookbook author Marco Leonelli, who prepares contemporary Italian and Mediterranean dishes using seasonal produce grown on-site or nearby.
A perfect retreat for families, this tranquil hilltop agriturismo (farm stay) offers simple, comfortably decorated accommodations on extensive grounds 5 km (3 miles) from the hubbub of San Gimignano. Directly on the Via Francigena, a medieval pilgrimage route, it's also ideal for those who like to walk; you can order a relaxing massage at the end of a day of trekking. A restaurant is on the premises, so you may choose to stay put in these pleasant surroundings for meals.
An elegant villa painted antique rose appears at the end of a tree-lined driveway perched on top of a hill off the main road just before Montemerano. It has expansive views and quintessential Tuscan charm. Tastefully decorated rooms—with curly ironwork or tapestries as bed headboards—are in both the main villa and a guesthouse. The farm that fans out around the villa produces fine wine and olive oil.
