Sydney
The Rocks

Discover the oldest district in Sydney on foot. In January 1788, the first convict ship from England arrived in Sydney - this peninsula (west of Circular Quay) was the site of the first settlement. Over the next hundred years, the port was busy with sailing ships and whalers, and the area expanded with shops, warehouses, hotels, merchant's houses, sailor's accommodations.

The Rocks Discovery Museum - Start your explorations at the free Discovery Museum. Find out about the aboriginal people who lived in Sydney before the arrival of Europeans, and see colonial artifacts, such as coins, a sandstone block inscribed with the date 1789, harpoons, whale's teeth, clothing and jewelry.
Walking tour - Here's our favorite walk through The Rocks.
Start at The Rocks Discovery Museum, go out, turn left on Argyle Street, then right onto Playfair Street. At Argyle Terrace, turn left into the very narrow passageway that goes through the building.
Here is Foundation Park, where kids can see the ruins of eight 19th century houses. All that's left is the foundation of the houses, but it's fun to walk through the rooms. Climb up the stairs to the top, which is Gloucester Walk. Turn right and walk down Gloucester Walk; at the end, turn right, and go down the hill on George Street.
As you walk down George Street, on the left, check out the clock tower and impressive ASNCo (Australasian Steam Navigation Company) Building, offices and warehouse built in the 1880's. Continue down George Street until you see the sign for Cadman's Cottage, then go left down the stairs.
Take a quick look into Cadman's Cottage, built in 1816 for a government officer. In 1849, the cottage was expanded and used to hold prisoners. Later the cottage was a home for retired sea captains.
To the left of the cottage on the grass is an imposing statue of Captain Bligh, who arrived in Sydney in 1806 as Governor of New South Wales. Turn left at Argyle Street and walk one block up, you'll be back where you started at the Discovery Museum.
Dawes Point Park - For those fascinated by cannons, at the end of the peninsula, underneath the Sydney Harbour Bridge, is Dawes Point. Here a fort was built in 1791 to defend the colony; today there's several big beautiful cannons to climb all over. It's also a nice walk back, going east around the peninsula, past the Park Hyatt hotel, and along Circular Quay West.
Fort Denison - Continue your explorations of historical Sydney with a trip to Fort Denison, situated on an island in the harbor.
The island, nicknamed "Pinchgut" was first used as a temporary jail for convicts, who were left on the island with bread and water rations, and no way of escape. In 1855, a Martello tower and fort was built to defend the harbor. Today, the island is open to explore, bring a picnic and sit out on the grass, and listen to the "1 o'clock gun" (it's actually a firecracker popping off).
If you want to see inside the Martello tower, sign up for the 1/2 hour guided tour from the national park service. Climb up the tower to see three massive original cannons (which can't be removed as the tower was built around them), and go down to the basement where gunpowder was stored in big barrels.
To visit Fort Dension without the tour, the Hop On Hop Off ticket from Captain Cook Cruises stops at the island, or book the Fort Dension Heritage Tour from the national park service (book the tour online 24 hours in advance, or stop into the visitor center upstairs at Cadman's Cottage).
Sydney Harbour Bridge - The Sydney Harbour Bridge is a famous landmark, and any bridge builders in your family will want to see it up close. To walk to the bridge, pick up the pedestrian pathway from Cumberland St. (a sign going up the stairs says "Pylon Lookout") and walk north. Climb Pylon Lookout, 200 steps up, with the best panoramic views of the harbor and Sydney Opera House.
Tip: It's a little tricky to find the pedestrian walkway from The Rocks, so here's a map.