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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.
Enchantment reigns at this tiny 13th-century countryside hamlet, part of the fiefdom of the aristocratic Florentine Guicciardini family and reinvented by the modern Count Roberto Guicciardini. A castle, church, and cobbled streets set the stage. Guest rooms vary in style; high wood-beam ceilings, terra-cotta floors, and modern bathrooms are the rule throughout. Apartments sleep as many as eight people and have as many as two baths.
Renaissance gardens, beautiful rooms with high ceilings and elegant furnishings, a panoramic pool, and expert staff are just a few of the things that make a stay at this 16th-century villa memorable. A short walk outside the small town of San Casciano Val di Pesa—with bus service to Florence—Il Poggiale sits on a ridge with spectacular views of the Chianti hills. An excellent breakfast is served on an outdoor terrace in fine weather, and the hotel's restaurant provides a buffet of antipasti along with a menu of Tuscan dishes for guests in the evening. The numerous public sitting rooms are intimate and cozy, and a small spa, with a sauna, massage room, and whirlpool tub complete the picture.
Stay in a fortified castle, which was built more than a millennium ago, was rebuilt during the Renaissance, and is now a charming inn and a prestigious wine estate where you can taste local vintages. Throughout the main building and two nearby farmhouses you'll find wonderful heavy wooden furniture.
Amid rolling vineyards and olive trees, this fattoria (farmhouse) produces fine wine and olive oil and accommodates guests in apartments (sleeping up to 6) and a separate house (sleeping up to 14). The main stone house retains its enormous stone fireplace and a 16th-century family chapel next door. Lodgings have traditional wooden furniture—some antique—and full kitchens; some units have fireplaces. Half-board is available.
Stroll around the wonderful gardens on this restored country estate dating from the 14th century, where guest rooms with arched windows and oak-beam ceilings are in two houses that look out on vineyards to the north and Siena to the south. The homey furnishings include antique wardrobes and ladder-back chairs. The dining room, open to guests only, has a prix-fixe menu. In summer, enjoy dinner by the pool surrounded by rolling green lawn.
Horseback trail rides through Tuscany's cowboy country are an integral part of the experience at this family-run country inn, where your hosts can arrange picnics, suggest itineraries, and organize weeklong tours. But nonriders don't have to mope at the bar—this agriturismo also has a pool and idyllic views. Rooms are plainly decorated with modern wooden wardrobes and desks; most are carpeted; some are enlivened by wood-beam ceilings.
Convenient to Rio Marina's charming town center and gravel beach, this comfortable hotel has pretty sea views, especially from one of the five rooms that have terraces facing the sea. Use of beach chairs and umbrellas is complimentary.
On a quiet street in the upper part of town, these unpretentious lodgings are given sparkle by the welcoming and friendly service of the owners, Roberto and Vittoria Giardinelli. Rooms are a bit kitschy and filled with family knickknacks, but each has a private, modern bathroom. Your lively hosts are on hand to serve breakfast in the morning and an honor bar is available to all guests. There's also a quiet garden terrace for lazy afternoons.
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.
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.
