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A turretted fortress from the Dark Ages anchors this wine and olive oil estate, where the eight apartments are spacious. There’s also a pool and mountain bikes for hire. No minimum stay.

A 12th-century castle and wine estate that rents six rooms (min 3 nights) and 2 apartments (weekly) in its complex of medieval buildings. Activities tend towards cantina visits and wine tastings, and the restaurant is good.

Fewer amenities but bags of style in this Renaissance villa. Six doubles and three triples (plus larger apartments available Apr–Sep). Three-night minimum in rooms; one week in apartments.

The four large, multi-level apartments, sleeping 4–6, are country-styled. Pretty gardens.

A rustic experience at long wooden tables – good, simple food in abundance. The family-run wine estate also has a shop where you can buy its farm products and wines.

Popular, hands-on grand duke who founded hospitals, gave poor girls dowries, promoted agriculture and hosted grand parties. He married Christine of Lorraine, whose family would inherit the grand ducal title.

Flagship store (and museum) for the firm that made cobbling an art form during Hollywood’s golden age.

Not wishing to miss out on the latest fashion, Florence has its very own Irish pubs; this one is the best.

This hilltop Etruscan settlement is a short ride from Florence on a No. 7 bus. The 11th-century cathedral was assembled using ancient Roman columns, and houses Renaissance sculptures by Giovanni della Robbia and Mino da Fiesole. The remains of a Roman theatre and baths are still used for summer concerts. The steep road up to San Francesco church, with its quiet cloisters and quirky missionary museum, passes a popular park, shaded by ilex and peppered with water-colourists reproducing its famous view of Florence.

Fiesole was the hilltop town that Roman Fiorentina was built to compete with. The town has a Roman theatre, small museums of art and archaeology, cool summertime breezes and views across to Florence.