Chester, United Kingdom

Ancient city walls, black-and-white mediaeval buildings, a racecourse dating back to the 16th century; there’s plenty here to titillate history buffs. But peek past the cobblestoned alleys and mock-Tudor architecture, and you’ll find that modernity has crept through the fortification’s cracks (Chester’s policy on shooting Welshmen entering after the 9pm curfew has been relaxed since the days of border feuds, thankfully), and a well-heeled one, too; the remnants of the famed Chester Rows walkways now front Jo Malone and Jaeger, Ladies Day at the racecourse attracts a moneyed country set and there are many sleek watering holes where you can kick back with a shake and stir; all the trappings for the perfect pint-sized getaway.

When to go

May is the time to rock up in your finest millinery: there’s a month-long festival of all things fast and horsy at Chester racecourse; but be sure to save your most camera-worthy headgear for Ladies Day (www.chester-races.co.uk/may-festival/ladies-day). The city tunes up for the MBNA Chester Music Festival (www.chestermusicfestival.co.uk) in June and the elegant programme of ensemble pieces kicks off with, erm, spear-wielding centurions at the Roman Weekend (the first weekend in June).

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