Nestled down one of Florence's quieter streets, this intimate guesthouse channels the character of old Tuscany. A homely vibe is unmistakable throughout the six well-equipped guest rooms, thanks to silk curtains paired with striped sofas, walls painted in washed rose or pistachio, four-poster beds and antique chairs. After a long day of exploring Italy's finest art collections, it's an ideal place to finish with a wine-tasting class in the dining room. Enjoy a breakfast of homemade cakes and jams with your hosts and fellow guests who will be more than happy to share their travel tips.

Halfway between Florence and Siena, this ancient but recently renovated farmhouse stands among vineyards, olive groves, cypresses and pines in the Chianti hills. The walls are covered with rough stucco, while handmade Florentine terracotta floors, ceilings featuring old wooden beams and arches throughout the building compliment farmhouse furnishing - think four-poster beds, warm-coloured textiles, pinewood drawers and oil paintings. On top of the views, a spacious pool and an exercising area in the tree-dotted garden, alfresco dining is available throughout the day. If you're visiting Sovigliano for a romantic getaway, book into the west wing of the building for a more private stay.

Set on a hilltop overlooking Montemassi Castle, this elegant B&B set in a 11th-century monastery promises panoramic views outside, while a rustic interior invites you to get merry in front of roaring fires of perfumed olive wood inside. Marrying history and nature, the impressive estate - which has belonged to the same family since 1650 - more than lives up to its Tuscan heritage. The self-catering rooms are surrounded by an organic farm made up of olive trees (the owners produce their own oil) and a small vineyard which create an proper countryside atmosphere, while canopy beds, peeling columns and a lack of TV and wifi contribute to the Tuscan holiday dream.

With the house dating back 500 years, Antica Casa is one of the oldest holiday homes in the region. Expect rooms filled with family antiques and paintings alongside restored 200-year-old frescoes which bring the Sistine Chapel right to your bedside. The walled garden with lemon trees and jasmine flowers has a terracotta terrace which is perfect for an afternoon snack, while the restaurant offers plenty of organic options. If you intend to explore the surrounding area, the guesthouse is located in the ancient hilltop village of Colle di Buggiano, which has its own beautiful churches and is only a short drive from Lucca and its Romanesque buildings. For a truly Italian experience, head out onto the streets and chat to locals perched on shady benches playing cards. They’ll merrily compliment you on your language skills – even if they are limited to “ciao” and “grazie”.

Step straight off a cobbled street onto the marbled floors of Campo Regio Relais. This is a top choice for boutique-style lovers and a gem in the heart of Siena’s old town, within strolling distance to restaurants and bars. With hints of French interiors, the restored building is a slightly toned-down version of more traditional Tuscan interiors yet comes with fresco-walled bedrooms, antique furniture, silk curtains and pastel-coloured details. The terrace overlooking the River Duomo, churches and medieval rooftops screams out for an evening Aperol as the sun goes down. Alternatively, head down to the sweetly named “honey bar” for a candlelit nightcap and selection of local snacks.