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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.
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.
Abundant breakfasts and communal dinner parties on Tuesday and Friday at the guest-only restaurant are just some of the things that make a stay at Fontelunga feel like you're staying with family. In fact, its owners, Paolo Kastelec and Philip Robinson, have gone to great lengths to make every space in this boutique hotel feel cozy and warm from the overstuffed armchairs in the living room to the bright Tuscan prints on the bedspreads. Outside, olive groves and perfectly trimmed hedges frame sweeping views of the Tuscan countryside.
