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Still trying to wrap your head around that name? We feel you. The aboriginal tongue-twister means “place of plenty” or “young black kangaroo” depending on who you ask. Either way, Woolloomooloo (shortened to ‘Loo by locals) is one of the most historic areas of Sydney and a real mecca for foodies thanks to its deluge of epic eateries.

Nestled right on the water and just a stone’s throw from Sydney Royal Botanic Gardens, Woolloomooloo has had a serious facelift in recent years. Once lush farmland and the location of the city’s naval base before becoming a ramshackle working-class area, the harbourside district is now buzzing with hip places to wine and dine – especially around jazzed-up Finger Wharf.

Wondering why you should make a beeline for Woolloomooloo while you’re in Sydney? Put simply, it’s crammed with first-rate restaurants, awesome Aussie pubs, genuinely interesting heritage sites and quirky cultural enclaves. To convince you, we put together the following guide…

What to see in Woolloomooloo

Despite its relatively small surface area, Woolloomooloo Sydney sure packs a punch when it comes to things to fill the hours. Check out:

Finger Wharf

Woolloomooloo’s most prominent feature has to be Finger Wharf: the longest timber-piled pier in the world. Back in the 1910s, it was the heart of Australia’s wool trade before becoming a major passenger port in the 1950s for newbies to the nation. The wharf was set to be demolished in the 90s before an ingenious idea came about to redevelop it into a luxe waterfront complex.

Nowadays, Finger Wharf is a magnet for hungry residents and visitors after great bars and eateries with Sydney Harbour outlooks, plus it’s home to one of the coolest apartment blocks in the city.

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Botanical gardens

The Royal Botanic Gardens

While technically part of the Central Business District (CBD), Sydney’s lush Royal Botanic Gardens border Woolloomooloo. Nearby spots worthy of a visit include the Domain parkland (which houses Sydney’s longest moving walkway beneath it) and the Andrew (Boy) Charlton Pool, where you can practice your front crawl with spectacular views of the harbour.

If you fancy a stroll, head deeper into the Botanic Gardens to wander through tropical hothouses and past trees teeming with fruit bats.

Old Fitzroy Theatre

Lodged inside the cosy Old Fitzroy Hotel (the closest thing you’ll get to a British pub in Woolloomooloo), the Old Fitz Theatre is one of the best kept secrets on Sydney’s indie theatre scene. The 60-seat venue, run by Redline Productions, in the building’s basement is no stranger to staging fantastic home-grown and world-renowned shows – from Shakespeare comedies to Oscar Wilde tear jerkers. What’s more, you can tuck into some decent pub grub (think rump steak and fish and chips) upstairs beforehand.

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Garden Island

Stroll southeast from Finger Wharf and you’ll eventually hit Garden Island. Despite its name, it’s actually attached to the mainland and has been a major naval base since the 1780s. Access is restricted by foot to civilians for obvious reasons, but it’s possible to catch a ferry from Circular Quay on the west side of the Royal Botanic Garden straight to the public Garden Island Wharf.

Once there, you can swot up on your Aussie naval history at the small, but surprisingly informative RAN Heritage Centre and have a gander around the landmark’s leafy grounds. There’s even a fragrant rose garden, plus lawn tennis courts which are apparently some of the oldest in Oz. The highlight of Garden Island is the old Signal Station whose roof terrace boasts arguably the best views of Sydney after the iconic Harbour Bridge itself.

Where to eat in Woolloomooloo

Whether you’re itching for Italian or craving some Aussie comfort food, Woolloomooloo Sydney has a cracking restaurant and café scene. Here’s our top three picks:

Otto Ristorante

Okay, so this is a bit of an obvious choice, but there’s a reason Otto is on everyone’s “top restaurants in Sydney” list. The sleek eatery overlooks the water on Finger Wharf and is no stranger to Australian A-listers. It’s easy to see why once you’ve had a forkful of the Moreton Bay bug linguine (don’t worry, they’re actually a type of lobster) or a spoonful of Otto’s decadent Trufflemisu.

There’s also an extensive vegan menu, with the pickled beetroot and cashew nut cheese ravioli being a fan-favourite.

Otto Ristorante is an outstanding option for a special occasion, but you’re better off going elsewhere if you want more bang for your buck.

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Instagram @ottoristorante
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Instagram @harryscafedw

Harry’s Café de Wheels

Another Woolloomooloo institute that’s undoubtedly worth visiting is this quirky restaurant on wheels – it’s supposedly been serving up some of the best pies in the Southern Hemisphere for over 80 years. Where to find it? Trust us, you won’t miss Harry’s Café de Wheels’ iconic awnings on Cowper Wharf Road.

Past customers include Prince Harry, Elton John, and Frank Sinatra, who’ve all queued up to sample Harry’s famous pastry-covered comfort food. The “Tiger” is the café’s signature dish – a rich beef pie topped with a layer of mashed potato, another layer of mushy peas and, finally, a hefty helping of gravy. Sound a bit too much? Select the chicken curry pie instead – you won’t be disappointed.

The Butler

Right on Woolloomooloo’s border with Potts Point is where you’ll spot this striking eatery. If the chic interiors – complete with leafy pot plants and rattan furniture – don’t entice you in, the mouth-watering scents of Ibero-American cuisine will. The tacos are the real winners, while the pan-fried habanero scallops have just the right amount of heat.

The Butler also has an impressive selection for veggies and vegans, plus the bottomless lunch is well-worth the $89 price tag. If you’ve booked a table for dinner, pop upstairs first to one of the best Woolloomooloo rooftop bars for an espresso martini and epic sunset views over the city.

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Instagram @thebutlersydney

Where to get your drink on in Woolloomooloo

Whether you’re happiest with a refreshing pint in your hand or you get a buzz from sampling weird and wonderful cocktails, Woolloomooloo’s bar offering is truly impressive.

The Tilbury Hotel

Not a hotel at all, but the home of one of Sydney’s best beer gardens. The Tilbury is conveniently positioned minutes from Finger Wharf on Nicholson Street, making it go-to for pre-dinner drinks. While some don’t rate the cocktails (you’re better off going to Peekaboo – see below), the wine list is ace and you’ll find plenty of beers on tap for a cheeky pint.

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Instagram @tilburyhotel
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Instagram @friscohotel

Frisco Hotel

It’s hard to miss the royal blue and white exteriors of Frisco Hotel when you’re traipsing down Dowling Street. The nautical-inspired décor is an ode to its past popularity with sailors (Garden Island is only 15 minutes’ walk away, after all) and there’s, naturally, plenty of rum on the menu.

Nab a table on the second-floor veranda and settle down for a balmy evening sipping your way through the cocktail list and snacking on Frisco’s tempting – and very well-priced – tasting plates. If you’re too sozzled to get home, there’s eight hotel rooms conveniently located upstairs…

Riley St Garage

This New York-inspired venue is located inside a disused garage (hence its name) and is a go-to in Woolloomooloo for sushi and sashimi. If you’re just looking to soak up its edgy interiors over a drink, pull up a stool at the inviting back-lit bar and peruse the list.

Riley St Garage has a great range of Aussie wines, plus a rotating selection of cocktails – many with a unique Japanese spin.

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Instagram @rileystgarage
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Instagram @peekaboo_bar

Peekaboo

Tiny yet effortlessly atmospheric, you’ll find Peekaboo tucked away down Bourke Street. The small space occupies a terraced cottage and is always rammed on weekends with thirsty locals and tourists in the know. Peekaboo’s cocktails are as they should be; strong, sultry and imaginatively named. The bar also has a decent selection of canapes if you get peckish, plus the happy hour deals are arguably some of the best in Woolloomooloo.

Awesome hotels in Woolloomooloo

There’s a handful of first-rate snooze spots in Woolloomooloo that’ll leave you feeling fresh as a daisy for a full day of exploring. Here’s the pick of the bunch, with an option to suit every bank balance:

Ovolo Woolloomooloo

This five-star beauty is located right on Finger Wharf and is, in our opinion, the district’s top hotel. All of Ovolo’s contemporary rooms have been thoughtfully designed to include the building’s original features, plus there’s imaginative artwork which subtly tells the story of the area’s past. Rooms might be pricey if you’re in the city longer than a weekend, but a free minibar and yoga mat definitely sweeten the blow.

Price: $$$

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Instagram @ovolohotels

Nesuto Woolloomooloo Apartments

Self-catering is the way to go if you’re in Sydney for a longer stint. Nesuto Woolloomooloo has a range of spacious apartments at its site right next door to the Frisco Hotel on Dowling Street, with each one coming with all the essential mod cons you’ll need. The décor is hardly designer, but it’s clean, modern, central and good value for money, so who cares?

Price: $$

Sydney Star Backpackers

If you’re hotfooting it around Oz with nothing but a pair of hiking boots and an overstuffed rucksack, the Sydney Star Backpackers is a good spot to bed down for a few nights in the city. Rooms are cosy and feature private lockers to secure your belongings. The best things about this hostel are the basic yet free breakfast and the rooftop terrace that’s the perfect place to chill out with a cold one at the end of the day.

Price: $

Close to Woolloomooloo

This up-and-coming area is close neighbours with another hip Sydney suburb – Potts Point. Once known as Woolloomooloo hill, the elevated neighbourhood is one of the oldest parts of the city and where you’ll find one of the oldest buildings: Elizabeth Bay House. The area is connected to Woolloomooloo via the famous McElhone Stairs – 113 steps that’ll really have you working up a sweat in summer.

Woolloomooloo is also within walking distance of the CBD, Haymarket and Circular Quay, where you’ll find Sydney’s most iconic attractions – think Sydney Opera House, Sydney Harbour Bridge, Sydney Chinatown and various amazing museums. Heading out of the city and can’t stand sitting in traffic? The M1 runs right through Woolloomooloo, giving you a quick getaway both north and south.

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