Sydney's Eastern Suburbs is a trendy region offering spectacular harbour views, a major dining and entertainment precinct and plenty of fine homes. Two main roads loop the harbour and ocean coastline meeting at Watsons Bay and this scenic route is a popular day trip for many holiday goers. The first road begins at Park Street and cuts through Hyde Park, Kings Cross, Rushcutters Bay, Edgecliff, Double Bay, Rose Bay and Vaucluse. The second road begins at Oxford Street and runs through Darlinghurst, Paddington, Woollahra, Syd Einfield Drive and Dover Heights before meeting with the first road in Watsons Bay.
Rushcutters Bay and Darling Point is home to up market houses and a playground to the wealthy with a club marina packed with some of the best yachts and ocean racers. It is also home to the Cruising Yacht Club of Australia which hosts the world renowned blue water classic Sydney to Hobart Yacht Race. If you're lucky enough to be holidaying in late December, the yachts jockeying for position on the harbour is quite a spectacle to behold.
Double Bay offers high fashion boutiques, art galleries and antique dealers - all high end retail shopping opportunities with no discount stores in sight. There are plenty of dining opportunities along the streetside bistro strip including the trendy Cosmopolitan Hotel. There are also a few casual eateries near the harbourside park and due to the large Jewish community, the area enjoys a distinctly European style.
Although a largely residential area, Point Piper and Rose Bay offer some of the most picturesque harbourside views and welcomes visitors. Home to the Royal Motor Yacht Club's city branch, it's no surprise that the homes in this suburb are extremely exclusive. There's plenty of waterfront dining and picnic spots as well as a scenic Foreshore Heritage Walk and Rose Bay also offers a flying boat service. These unique scenic flights operate to Sydney's extreme north on the Hawkesbury River. Aboard a high-wing aircraft, the scenic flight offers spectacular aerial views.
Named after the historic Vaucluse House, Vaucluse is a leafy old residential suburb enjoying sweeping harbour views and impressive cliffs overlooking the ocean. A scenic walking track stretches from Vaucluse, through South Head, The Gap and the headland finishing up at HMAS Watson in Watsons Bay, a natural reserve offering access to historic Camp Cove.
Watsons Bay is also home to a great range of seaside dining including the famous Doyle's on the Beach as well as more casual options along the wharf. Ferries run from Circular Quay to Double Bay, Rose Bay and Watsons Bay and are an alternative way to experience these stunning holiday destinations. The trip along the harbour is an experience in itself and offers some of Sydney's best water views.