7 Best Hotels in Southern Tuscany, Tuscany

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.

High above Sorano, this austere-looking 11th-century Orsini castle has spectacular views of the town and surrounding countryside. Wood-beam ceilings hang above white and pastel walls in most rooms, and windows have dark-wood shutters. A careful mix of antique and modern furniture—Rococo chairs and upholstered couches—makes for a pleasant and comfortable stay. The hotel closes for some time during the winter; the length and month of the closure vary annually.

Inspired by the beach resorts of the Greek isles, La Guardia is a minimalist retreat with sweeping sea views and plenty of wicker lamps, seagrass accents, and wooden furniture. Aperitivi on the terrace are a large part of this hotel's appeal, as is the Mediterranean menu conceived by chef Milena Andretto and prepared using only island-sourced ingredients.

The guest rooms at this 14th-century palace are named for signs of the zodiac, but the astrological reference stops at the painted symbol on the door, as each elegant room is unique—an antique sewing-machine table serves as a nightstand, a medieval-looking chandelier with a forged-iron ring and a globe hangs from a ceiling, elegant striped silk covers a wooden settee. Some rooms have ivory-color drapes hanging from baldachin beds—iron canopy beds with a painted medallion on the headpiece. A lovely garden opens behind the hotel. Five cheaper rooms, named for constellations, are available in an annex.

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. 

Designed by postmodernist Italian architect Paolo Portoghesi, this resort hotel has sweeping views of the Maremman countryside on all sides. The pool and gardens are magnificent, the rooms are tastefully decorated, and the staff is helpful and friendly. 

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.