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Wonderfully old-fashioned, its huge rooms stuffed with a mix of antiques and classic 1950s and 60s furnishings. Run by a Welsh ex-pat.

Paolo is the friendliest hotelier in town, keeping his little jewel of an inn shipshape. All but two of the smallish but nicely furnished rooms are on the front, and if you lean out you can see the Romanesque façade of San Michele.

In a centre plagued by either overpriced or grotty hotels, tiny Etruria stands proud. Its immaculate rooms with contemporary decor are great value, and the only drawback is the 12:30am curfew. Book early; there are only 13 rooms.

Everything an island retreat should be. The terraces of most rooms enjoy expansive views over the owner’s vines and olives to the wooded headland of Sant’Andrea. You can walk these paths to the resort’s beach or to a secluded cove. Rooms are simply furnished, tile-floored and comfortable.

Tiny, much-requested hotel in Mauro and Nadia’s own home (Mauro may even entertain you with his accordion). Perched atop St Catharine’s convent, the whitewashed rooms are quiet, and two have views of the Duomo.

This converted farmhouse has kept a strong country air, with rustic antiques and bucolic vistas. Commodious rooms open off cosy lounges. There’s also a small pool.

Another great family-run place, tucked on a side street off the town’s main drag. Rooms are cosy, many with rural views and creaky antique furnishings. As an added attraction, a stretch of medieval town wall passes through the property.

The archetypal Florentine pensione of terracotta-floored rooms and wide halls cluttered with worn antiques and overstuffed easy chairs. The airy top-floor loggia looks out over Piazza Santo Spirito. A place for Romantics.

Labyrinthine old budget hotel in an 18th-century palazzo. The comforts are basic, but it’s well-maintained and friendly. The rooftop gardens have a gate with direct access to the city’s pretty public park.

Just a few steps off the main piazza, the Italia offers standard comforts and modern furnishings; a few rooms even come with views of the countryside, beyond Cortona’s rooftops.