Book in advance. Obvious, but it has to be said: Villas get booked out in advance, particularly in Tuscany in summer. Many agents have dozens of mouth-watering options on websites. Start your search at Cuendet, Invitation to Tuscany or Traditional Tuscany. Think spring and fall, not July or August. In summer peak season, availability is trickier and prices predictably higher. Still, you can find nice villas, often with pools, that sleep six from £2000 (US$3050) per week — or about US$70 per person per night. But! That same villa is often half price from mid-April to mid-May or October to mid-December. Book by the week, not by the day. You’ll look silly trying to get one for two days. Prices are set by the week.



If not Tuscany, Umbria? Slower-going than Tuscany, Umbria has fewer visitors and many villa rental choices too, and its hill towns make great back-up daytrip fodder, like at St Francis of Assissi’s birthplace with mile-long walks to sanctuaries between olive trees, or the cliff-side Orvieto and its wondrous 13th-century Romanesque cathedral (and one of our favorite Italian wines). If not Umbria, Le Marche? Jessica Spiegel of Italylogue.com tells me ‘Umbria’s becoming increasingly popular as people spill over from Tuscany — if you’re really trying to get away from that, keep going east to Le Marche‘. It’s a great area, with mountains and hill towns like the lively little Urbino, a World Heritage site. (There’s the Adriatic coastline too, though much of it is lined with unflattering high-rise hotels.) If not villa, agroturismo? Snatching a rural base on a working farm is a nice back-up to a villa — some are simple, rustic affairs, other more luxurious. Also information centers can help track down these last minute (I showed up room-less at 4pm in San Gimignano’s center once and they got me into a lovely nearby farm with a pool and an unforgettable outdoor dinner overlooking their vineyard). Lonely Planet’s Alex Leviton recently found a super one over in Le Marche, Urbino’s Locanda della Valle Nuova: a working organic farm with six rooms, home-grown truffles and horse rides. Count me in.