Perched on a cypress-striped hill overlooking the little town of Montelupo, Cantagallo (rooster in Italian), has a clutch of self-contained apartments painted rusty red and complete with fridge, cooker and bathroom. Private courtyards, market umbrellas and a pool view provide the perfect spot to indulge in Cantagallo's homemade pecorino cheese, olive oil, wine and jars of caper tapenade and artichokes. The charming "osteria" run by the family nonna who speaks a little English is seasonal and hearty: linguini with hare ragu and fennel flan. A train from Montelupo puts you in central Florence in 22 minutes. From $125 per night for two.
See tenutacantagallo.it/en/
RENELLO
Renello's extra virgin olive oil was the official oil at this year's Milan expo, a tribute to the skills of keen agronomist Giacomo. He and wife Rosella own this characteristic old farmhouse set amid rolling woodlands and olive groves near the town of Traquanda, in an oasis of Tuscan serenity. Renovated wings and outhouses have been converted to rooms with a provincial Italian feel – fresh flowers, throw cushions, decorative plates and other nods to nostalgia. Dinner is served communally on a huge table with Rosella sending authentic Tuscan dishes from the kitchen, while Giacomo pours vino and enlightens guests about local truffle hunting, olive oil tasting and hilltop towns including Montepulciano and Montalcino. There's a pool too. From $175 per night for two.
See renello.it/
IL CIPRESSO
Il Cipresso's seven suites are lovingly integrated into the shuttered three-storey villa, mingling the grandness of a high-end hotel (air-con, a writing desk, complimentary wine, a pool) with the warmth of a guesthouse. Charming host Alberto, whose great grandfather purchased the property in 1918, has turned it into a boutique organic farm, with olive trees, vineyards and gardens that in turn contribute olive oil, organic vinsanto wine, honey and jams to the farm offerings. An old stone barn has been converted into a sweet little trabaccaia, where Alberto serves authentic dishes inspired by local produce and his own wine. The Etruscan town of Cortona, which featured in the novel Under a Tuscan Sun, is a short drive away. From $155 per night for two.
See ilcipresso.com/
LOCANDA ROVICCIANO
Geese strut around this 17th century stone building like they own the place, but the kudos should go direct to delightful owner Andrea Leonelli who has made culinary magic in one of the quietest corners of Umbria. Al fresco tables set with white tablecloths, glittering cutlery and chinking glassware, are perfect for sunny days. Indoors, stone walls and low-slung ceilings create a moody ambience suited to the hearty homemade pasta dishes and free-flowing red wine. There are three renovated apartments available, with price packages that include a la carte meals. Leonelli conducts cooking classes that can run to four blissful days. Local hilltop towns include Montefalco and Foligno. From $85 per night for two.
See locandarovicciano.it/
BARTOLI
A narrow winding road climbs more than 1000 metres to Bartoli, a stone villa in the hilltop village of Patrico on the slopes of Monti Fionchi. Opened in 1988, Umbria's first agriturismo has guestrooms that accurately reflect the simplicity of rural Italian life. Guests can go truffle hunting with patriarch Luca and his dogs, or horse riding in countryside that has views to the Appenines. Matriarch Marcella's lunch is served at a convivial communal table in the main dining room. Here you're more likely to dine with farmhands and family than tourists on unfussy dishes that are gusty and delicious – truffle ravioli, wild boar salami, pecorino cheese and lamb sweetbreads. The local drop is Sagrantino di Montefalco. From $110 per night for two.
See agriturismospoleto.net
GALIZIA
Bounded by green woods and sidled up to the Ticino River, it's hard to believe Milan International Airport is only 20 minutes away. This working farm, producing berry fruits, vegetables and beef, has spic 'n' span contemporary rooms (more like a hotel than guesthouse) built into its recently restored Tuscan yellow farmhouse buildings. Guests can dine in on Galizia produce such as a salted meats charcuterie plate, beef ragout, or sample Milanese specialties such as "elephant ear" with crunchy potatoes. An airy and light-filled farm shop operates like a café where visitors can buy Galizia's homemade berry ice creams, honey and jams plus locally sourced bread and craft beer. From $140 per night for two.