Why pay top dollar for a luxury vacation when it’s possible to have it for less? A high-end trip without a premium price tag is possible anywhere in the world, but your approach needs to be tailored to your destination. Here, locals in five famously expensive cities — London, Paris, San Francisco, Singapore and Sydney — share luxury for less tips.

London

TIME IT RIGHT London has some particularly busy periods with sky-high hotel rates, according to Paula Fitzherbert, a lifelong Londoner and the head of communications for the five-star hotels Claridge’s, Connaught and Berkeley. They include June, during the Chelsea Flower Show, Ascot and Wimbledon, and the fashion weeks in February and September. These times asides, rates are least expensive on Sunday nights when occupancy is at its lowest. “A stay could be half the price, compared with another day of the week and you’re likely to get free amenities,” Ms. Fitzherbert said. The properties she represents try to offer Sunday night guests extras such as a bottle of Champagne, breakfast and a room upgrade.

James Manning, the global projects editor for Time Out London, encourages visiting either at the end of August or anytime in November. Flights and hotels are less expensive, and several noteworthy and free events take place. One of the largest street festivals in Europe, Notting Hill Carnival, is in August.

DINE AND DRINK SMARTLY Skip white tablecloth dining. Mr. Manning said that some of London’s casual and affordable restaurants, such as the Taiwanese spot Xu, outperform many expensive Michelin-recognized joints in atmosphere and flavor. To indulge in decadent cuisine for a bargain, head to a food hall in a luxury department store like Harrods or Selfridges, Ms. Fitzherbert said (she does, too). “You can buy small portions of rare cheeses and handmade chocolates, and the stores often give out free samples on weekends,” she said. She also suggested taking advantage of the widely available and attractively priced pre- and post-theater menus at otherwise expensive restaurants like The Ivy and Savoy Grill and enjoying an evening drink at an upscale bar like the Connaught Bar for less than $20 — an order usually comes with olives, nuts and other snacks.