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Sydney : Itineraries

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  • Morning

    Catch a ferry from Circular Quay to the quaint Darling Street Wharf. Enter Illoura Reserve and walk south beneath she-oaks and other native trees to Peacock Point ’s views across to Darling Harbour (see Darling Harbour & Chinatown). Johnston Street has great views of Anzac Bridge . Head back to Darling Street and admire some of Balmain’s finest residences. Turn into Killeen Street and wander down through Ewenton Park. Around the corner is grand Hampton Villa overlooking the docklands, home of Sir Henry Parkes. Back at Darling Street, get a drink at the pleasant London Hotel. Then, window-shop all the way to the Town Hall. Finally, backtrack to Go Bungai at 333 Darling Street for the best Japanese lunch in town.

    Afternoon

    After lunch, continue back down Darling Street to Mort Street and turn left. At the end is Mort Bay Park, site of the former Mort’s Dock shipyards, named for Thomas Mort (see St Andrew’s Cathedral), which is now open harbourside parkland. Follow the shoreline around to the steps leading up to Wharf Road via Ronald Street. This lovely street leads to Snails Bay and the historic Birchgrove Park. A path traces the shoreline to Louisa Road, which has some seriously expensive real estate. Turn right and head towards Yurulbin Park for some spectacular harbour views before catching the ferry back to Circular Quay.

  • Morning

    Pack the bare essentials and catch the ferry to Manly Wharf. Cross The Esplanade and follow The Corso down to Manly Beach . After paying homage to William Gocher (see Manly Beach), head south and follow the path around to Cabbage Tree Bay, where you’ll find the delightful Fairy Bower rockpool and Shelly Beach (see Manly), both of which are perfect for children. Then extract your credit card and enjoy lunch at the classy Le Kiosk , voted the most romantic restaurant on the East Coast by the New York Times.

    Afternoon

    Leave the beach via Bower Street and follow this around to College Street, past the million-dollar mansions overlooking Manly Beach. Turn right into Reddall Street, left into Addison Road, and left again into Darley Road. Head uphill and take a peek over the stone walls at the Former St Patrick’s Seminary . Continue past the hospital and take the right fork leading into Sydney Harbour National Park . Pass beneath the sandstone arch and take Collins Beach Road on your right. This wends down through a lovely shaded gully to the Police College. A small path on your right leads to the secluded Collins Beach , one of Sydney’s hidden secrets. A path at the end of the beach leads to Stuart Street, which takes you back to Manly.

  • From the Darlinghurst Court House (see Darlinghurst Court House & Old Darlinghurst Gaol) follow Oxford Street as far as the imposing sandstone walls of Victoria Barracks. Turn left into Glenmore Road, which has a cluster of small but classy boutiques. Gipps Street leads to Liverpool Street, which is a winding road of elegant double-storey terraces reminiscent of some of London’s wealthier Victorian districts. Hogarth Galleries , is down Walker Lane. Rejoin Glenmore Road and follow this winding and busy thoroughfare to Five Ways, a quaint little intersection with several good cafés, including Gusto.

    After coffee and a snack, head up Broughton Street to the narrow laneway and steps on your left. At the bottom of the lane turn right and walk down to steep Cascade Street. Turn right and walk uphill past Windsor Street’s incredibly narrow terraces to Paddington Street. Follow this elegant fig tree-lined avenue up to Jersey Road, passing Tim Olsen Gallery and several of Sydney’s premier addresses en route. Turn right into Jersey Road, then into narrow Caledonia Street, which leads back to McGarvie Street where several eccentric balconies overhang the narrow pavement. Turn into Underwood Street and you’ll find the Grand National Hotel and the London Tavern, both happy to serve you a well-earned drink. The latter is on William Street, which also has several boutiques.

  • Morning

    Head north across the Harbour Bridge and follow the signs to Windsor . After a pit stop at the 1815 Macquarie Arms Hotel on George Street, backtrack to Pitt Town Road and follow this northwards. It becomes Cattai Road and then the Wisemans Ferry Road, passing through farmland and bush before dropping down to Wisemans Ferry on the Hawkesbury River . Take the southern ferry across the Hawkes-bury and follow the incredibly scenic road that tracks the Macdonald River as far as St Albans , where you can enjoy lunch at the 1848 Settlers Arms Inn.

    Afternoon

    Head back towards Wisemans Ferry along the other side of the Macdonald River until it meets the Hawkesbury River. Follow the river beneath its sandstone escarpments and through the isolated riverside townships of Gunderman and Spencer before climbing up through the forest to Central Mangrove. Drop down to Calga via Peats Ridge and take the Old Pacific Highway south to the Hawkesbury again. Cross the river and take the turnoff to the small fishing and boating township of Brooklyn. Enjoy an ale at the Anglers Rest Hotel or take a 5-minute ferry trip across to Dangar Island’s idyllic Island Shop for a coffee or light meal overlooking the water.

  • Morning

    From Circular Quay follow Loftus Street to Macquarie Park, exhibiting the anchor from the First Fleet HMS Sirius. Across the road is the 1876 Lands Department Building, seat of early European land ownership. Its façade features statues of explorers, including Ludwig Leichhardt and Major Thomas Mitchell. Head to Martin Place via George Street and check out the GPO ’s Pitt Street colonnade with characters representing trades, professions and industries, then sneak a peek through the windows of Martin Place’s grand banks. Turn right into Macquarie Street (see Macqurie Street Precinct), taking care not to bump into one of the city’s “wigs”, for this is Sydney’s legal district. At Hyde Park , note the lovely Art Deco Archibald Fountain and wander down the glorious avenue of fig trees to Park Street. Turn right and take a seat outside the classy Bambini Trust Café at 185 Elizabeth Street. Sample an antipasto while you peruse the Specials menu and the passers-by.

    Afternoon

    Head to Market Street and turn left: Sydney Tower is one block down on your right and the Pitt Street Mall (see Pitt Street Mall) two blocks down. Turn into the mall and left into the Strand Arcade and it’s time for a caffeine fix at Luxe Espresso. Exit at George Street and turn left. On the next corner is the QVB where you can spend the rest of the afternoon happily splurging.

  • Begin at the El Alamein Fountain. Walk down Macleay Street and you’ll pass the Rex Hotel, site of Sydney’s first gay bar in the 1940s, the Bottoms Up. Turn into Greenknowe Avenue and walk down the hill and left into leafy Ithaca Road, where you’ll catch glimpses of the harbour. Beare Park is tucked between the high-rise apartments. From the wharf there’s a good view of Boomerang, the Spanish Mission mansion. Walk up Billyard Avenue to Elizabeth Bay House, passing the Del Rio, another Californian Spanish Mission building. Steps on Onslow Avenue will bring you back up the hill to Macleay Street.

    Turning right, stroll down to Yellow Bistro . Have a coffee and a sweet treat on the porch.

    Refreshed, walk down Challis Avenue into Embarkation Park for great views of the Naval Base at Woolloomooloo. Continue up Victoria Street, past the terrace houses to Hughes Street. Turn left into the Tusculum Street, and then Manning Street. Next door to Tusculum Villa, the Werrington and the Wychbury are some of the best Art Deco buildings in the Cross.

    On your way back up Macleay Street, pop into Orwell Street to see the old Metro Theatre, where a nightclub roared in the 1930s. Finish up your afternoon tour with a drink at the Bourbon, a very stylishly revamped Kings Cross dive bar.

  • Morning

    Catch the Bondi Explorer or a 325 bus from Circular Quay and get off at Nielsen Park. It’s a short walk downhill to Greycliffe House and Shark Beach. When you’re ready, walk back to Vaucluse Road, which becomes Wentworth Road. The entrance to Vaucluse House is further down on the right. Continue along Wentworth and take the first right into Chapel Road. WC Went-worth’s gloomy mausoleum is just up the hill on your left. Steps lead from behind the mausoleum to Fitzwilliam Street. Turn right and walk downhill to the lane on your left, which takes you across the Parsley Bay suspension footbridge. Take the steps on your left leading up to The Crescent and follow this around until you reach Palmerston Street, which leads to Watsons Bay Pilot Station. Follow Marine Parade north to the ferry wharf and lunch at Doyle’s (see Doyle’s On The Beach).

    Afternoon

    After lunch, walk to Short Street at the end of the beach, turn immediately left into Cove Street, and then left again into Pacific Street. This leads up to Green Point overlooking Camp Cove. After enjoying a swim here, or at Lady Bay Beach further on, follow the path along the clifftops to South Head. Retrace your steps and catch the ferry from Watsons Bay back to Circular Quay, or the bus from Hopetoun Avenue.

  • Morning

    Start your day in classic Newtown style with a strong coffee at Barmuda, 283 Australia Street. Then follow Australia Street to Lennox Street and turn right. At the end is St Stephen’s Church, designed by Edmund Blacket (see St Andrew’s Cathedral). Beside the church is the entrance to the historic, peaceful Camperdown Cemetery. Soak up the Gothic atmosphere before heading back to hectic King Street. Check out the bookshops, cafés and funky clothing stores that run almost as far as Little Queen Street. Turn left, cross over Carillon Avenue and enter the manicured grounds of the Sydney University. Turn right into Physics Lane, left into Fisher Road, and right into Manning Road, reaching the archway that leads through to the Main Quadrangle. Pass beneath the Gothic Revival clock tower and wander down University Avenue to the open space of Victoria Park. Finally, head to bohemian Glebe Point Road to Badde Manors for lunch.

    Afternoon

    Follow Glebe Point Road to Pendrill Street, turn left and follow the scent of incense downhill to the Sze Yup Temple. Turn right into Edward Street, left into Eglington Lane, and right again into Edward Lane to reach Jubilee Park. The Pope Paul VI Reserve can be found in the northeast corner. When done, catch a 431 or 434 bus back to town.

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