Before it opened its doors in 1993 as one of the finest boutique hotels in Sydney, it was once home to Dr Frederick Harrison Quaife, who was a founding father of the British Medical Association and son of philosopher Barzillai Quaife. Then it became a Masonic Hall and a Ladies College. There are 36 rooms and eight suites – including a few dog-friendly ones, and you can even stay in Dr Quaife’s former room, which overlooks Queen Street. Its black marble fireplaces, oak furniture, grand staircase and even more grandiose Victorian-era rooms are well suited to the affluent area of Woollahra, which has leafy streets packed with galleries, million-dollar estates and high-end boutiques. Expect eccentric types discussing Dostoevsky in the Reading Room, high tea with fluffy scones and traditional teas and even jazz nights, where a pianist will tinkle the ivories of the baby grand piano in the lounge. The hotel’s Quaifes Cafe and Restaurant serves a la carte dining, and there are plenty of top-notch restaurants and pubs situated along Queen Street and nearby Oxford Street.