(CNN) -- The sun-soaked, beach-scattered metropolis of Sydney has a reputation as one of the world's most vibrant and livable cities.
Nicknamed the "harbor city," Sydney's seductive waterfronts bloom with sails, and never more so than on December 26, when Port Jackson, home of the dramatic Sydney Harbor, is the starting point for the Rolex Sydney to Hobart yacht race.
As the last remaining yachts cross the finish line, in what is widely regarded as one of the most difficult races in the world, we take a look at a more laid back and luxurious way of seeing Sydney by sailboat.
Where to sail
"Those interested in sailing Sydney should never miss cruising out of the main Sydney Harbor," says Shawn Low, Melbourne-based travel editor of the Lonely Planet guides.
According to Low, sightseeing by sailboat offers a unique perspective on Sydney's most famous landmarks. "As you head north, Sydney Opera House will loom on your right and the Sydney Harbor Bridge on your left," he said. "These are Sydney icons and simply shouldn't be missed."
From the main harbor take a cruise to the Sydney Heads -- the impressive headlands jutting out onto the Tasman Sea -- which act as signposts to Port Jackson, suggests Edward Penn, general manager of yacht chartering firm Sydney by Sail.
"First, stop off at the fish markets to stock up on fresh prawns, oysters and a bottle of bubbly," said Penn. "Along the way check out the 18th century penal site of Fort Denison, just past the Royal Botanical Gardens."
Ben Roberts, from Superyachts.com, recommends Darling Harbor, situated on the western outskirts of the Sydney central business district. "It's another gorgeous waterfront destination not to be missed," he said. "Near here you'll find the Sydney Aquarium, beautifully tendered parklands and some fabulously unique museums, including the Powerhouse, where creativity is the muse."
Where to swim
According to Roberts, no trip to Sydney would be complete without visiting the world-famous Bondi beach. The seven-kilometer sail east of Sydney Harbor is a must, says Roberts, adding: "One look at its perfectly golden sands melting into deep blue waves and there is no question as to why it is recognized as one of the best in the world."
But Penn notes that tourists need beware, the beach's south side has a famously powerful rip current, ominously known as the "Backpackers' Express" because of its adjacency to the local bus stop, and the reluctance of tourists to walk the length of the beach to safer swimming.
Further afield, Merewether Beach, in the neighboring metropolitan district of Newcastle, is the setting for Surfest. Held in March, this annual surfing competition is Australia's largest. Also around Newcastle is the 32 km-long Stockton Beach that Low says is one of the best places in the world to "rip across the dunes on a four-wheel drive, a dune buggy, or jump on a dune board."
Other particularly notable beaches around Sydney include the glamorous Tamarama, home to the world's first surf lifesaving club, and for soap-opera fans there's Palm Beach -- the site of popular Australian TV series "Home and Away."
Where to eat
"Top of the list would be Peter Gilmore's Quay Restaurant," says Low. "Quay has the advantage of a fine location across from the Sydney Opera House but diners might be too distracted by the seafood-focused food to enjoy the view."
So what's on the menu? "Think sea pearls and crab congee, slow-braised pig cheek with ginger milk custard, fresh palm heart, green-lipped abalone, Tasmanian wakame and chestnut mushroom consomme," he said.
While not exactly at the harbor, Low says that Tetsuya's is arguably Sydney's most renowned restaurant. "It's only a five-minute drive south of the harbor and you have to book early," he said. Visitors should also make sure to be in good company -- it's an 11-course degustation over four hours."
Roberts adds that the Victoria Room in Darlinghurst, an inner-city eastern suburb of Sydney, is full of colonial style and "serves up a combination of excellent drink, Mediterranean nibbles and of course, high tea."
Where to chill
Al-fresco dining, bike rides through the park and open-air music performances are all par for the course around the Rocks -- Sydney's historical harbor-side precinct.
According to Roberts, the region is "a maze of cobblestone streets and leafy courtyards lined with the city's oldest restaurants, pubs and cafes sitting alongside bustling markets selling local artworks and traditional Australian fare."
Emily Smith contributed to this report