Fun and Unusual Things to do in Woolloomooloo

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[{"address":"Andrew (Boy) Charlton Pool","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.86350476065641,"longitude":151.22159819999996},"media":[{"type":"text","content":"# Have a Swim and a Sunbathe\nThis is another one of those sights that’s not technically in Woolloomooloo, but overlooks it, so I’m going with it.\n\nAndrew Boy Charlton pool is located on the cliffs close to the domain and it has a view of the water, Woolloomooloo and the battleships that dock at Garden Island.\nIt’s also one of the best places in the Sydney CBD to swim and sunbathe.\n\nIt gets extremely busy at weekends so, try and time your trip in the week if you can.\n\nOh, and the pool is salt… that totally surprised me when I swam there."},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F9.webp?alt=media&token=cbfc6347-d3d7-4e58-afdc-e8db2d1b5baf"},{"type":"link","content":"https://abcpool.org/"}]},{"address":"Dual Nature","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.86361126065645,"longitude":151.22148550000003},"media":[{"type":"text","content":"# Listen to the Sound Sculptures\nEven if you don’t want to swim, you should head toward the pool as in the water nearby is a set of sculptures called Dual Nature by artist Nigel Helyer.\nThey’re supposed to represent ships launching to tie in with the maritime history of Garden Island (where you see the big grey battleships opposite). "},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F10.webp?alt=media&token=358e4342-4912-4568-93df-b92f8f9c3fbf"},{"type":"link","content":"https://www.cityartsydney.com.au/artwork/dual-nature/"}]},{"address":"Cowper Wharf Roadway","location":{"longitudeDelta":0.10218818160659443,"latitudeDelta":0.09219986310369421,"latitude":-33.86735811065801,"longitude":151.22320209999998},"media":[{"type":"text","content":"# Head into Artspace\nYou could easily walk past this Art Gallery on Cowper Wharf Road if you didn’t know it was there, but don’t.\n\nThe two-floor space won’t take long to cover, but the exhibitions change regularly and there’s always something a bit surprising to see.\n"},{"type":"link","content":"https://goo.gl/maps/KbGm3yMgFuzjJEpq6"}]},{"address":"Ovolo Woolloomooloo","location":{"longitudeDelta":0.10218818160659443,"latitudeDelta":0.09219986310369421,"latitude":-33.8685003616726,"longitude":151.22052544999997},"media":[{"type":"text","content":"# Or at Least Meet The Gnomes\nThe Ovolo hotel group pride themselves on doing things a bit differently and one such touch is the gnome they use to reserve your table in their in-house bar,\nLook, how can you not love him!\n\nYou’ll have to have a table booked to make use of him but, considering these are the type of cocktails you’ll find at the bar, why wouldn’t you want to do that?\n"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F4.webp?alt=media&token=5b94e12f-7d31-497c-9e84-c17b966bac2c"},{"type":"link","content":"https://ovolohotels.com/"}]},{"address":"Alibi Bar & Kitchen","location":{"longitudeDelta":0.10218818160659443,"latitudeDelta":0.09219986310369421,"latitude":-33.8690932606587,"longitude":151.22021875000002},"media":[{"type":"text","content":"# Get Your Vegan on at Alibi\nNot keen on the concept of munching cow wrapped in pastry sitting by the side of the road, then get your glad rags on and head off for a posh vegan dinner at the Alibi restaurant at the Ovolo Hotel.\n\nThe chefs at Alibi are seriously creative – when I went,they served a dehydrated watermelon poke dish that blew my mind.\nLooking at the menu today, there’s choices like a mushroom-stuffed Yorkshire pudding and kimchi dumplings to choose from.\n\nYou can order dishes individually or let them choose for you and try the 8-course degustation menu. You won’t be disappointed.\n"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F3.webp?alt=media&token=e91955ee-d0de-4432-9c34-3d726916deb4"},{"type":"link","content":"https://alibibar.com.au/"}]},{"address":"Harry's Café de Wheels - Woolloomooloo","location":{"longitudeDelta":0.10218818160659443,"latitudeDelta":0.09219986310369421,"latitude":-33.869271960658715,"longitude":151.22120099999995},"media":[{"type":"text","content":"# Eat Sydney’s Most Iconic Pie\nThe pies at Harry’s Cafe de Wheels have been sampled by everyone from Elton John to Joe Jonas and, while they now have a couple of locations around the city, the Woolloomooloo one is the original.\n\nAnd the one with the prettiest view!\n\nIt’s located right on the water on the Cowper Wharf Roadway\nGrab a plain pie or go for the classic Tiger Pie which topped with mashed potato, peas and gravy. Perch on one of the limited seats – or balance it on your knee with a view of the warships and experience a piece of Sydney history and one of it’s most iconic foods.\n\nPlus it’s a bargain at under $10 for a pie. There’s not many meals under $10 in Sydney!"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F2.webp?alt=media&token=250406eb-743c-4d4e-b5d5-8ca374ccd8d7"},{"type":"link","content":"http://harryscafedewheels.com.au/"}]},{"address":"The Tilbury Hotel","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.86978156065894,"longitude":151.220418},"media":[{"type":"text","content":"# Hit the Pub\nTalking of pubs… there’s a lot of them in Woolloomooloo.\n\nMy first choice is the Woolloomooloo Bay Hotel; it’s down to earth but not too shabby – and the tables on the balcony have a nice view of the water.\n\nNext to this is The Bells, it’s, let’s say, an unfussy pub, and, rumoured to be a drinking hole of actor Russell Crowe who has an apartment in the swanky Cowper Wharf building opposite. Probably because no-one in here will give two figs who he is!\n\nThe Tilbury is where the bright and the beautiful go – especially on a Sunday afternoon.\n"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F13.webp?alt=media&token=17ebe668-a472-452f-9ca5-676b75d4a8be"},{"type":"text","content":"The Frisco is another good choice. It has a few outdoor tables and a really nice feel about it. I don’t go here as often as I probably should!\n\nLastly, there’s the Old Fitzroy Hotel, which is a right mix of characters. Regulars include playwright Louis Nowra and he immortalised the pub – and the local area in his book Woolloomooloo."},{"type":"link","content":"http://www.tilburyhotel.com.au/"}]},{"address":"The Big Matchsticks","location":{"longitudeDelta":0.10218818160659443,"latitudeDelta":0.09219986310369421,"latitude":-33.86978601065896,"longitude":151.21778874999995},"media":[{"type":"text","content":"# The Big Matchsticks\nLocated on a patch of land just behind the Art Gallery of New South Wales (a must-visit if you like art), these are not, technically, one of Australia’s iconic big things, but instead a piece of art by famed local artist Brett Whiteley.\nThe Matchsticks are 8 metres high and their official name is Almost Once.\n\nApparently, they represent the idea of living life to its fullest until you finally burn out. Somewhat ironically, the sculpture was completed a year before Whiteley died from a drug overdose.\n\nThe local cockatoos, obviously have no sense of art or history and have decided that the matchsticks make brilliant chewing posts so, they do have to be restored every now and again!"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F1.webp?alt=media&token=8bff3343-8843-4277-8cfb-8413ac9bf252"},{"type":"link","content":"http://www.artgallery.nsw.gov.au/"}]},{"address":"Woolloomooloo","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.870333038275696,"longitude":151.21840939985074},"media":[{"type":"text","content":"# Spot the Fake Doors\nThese doors on the back of the Elephant Backpackers on Crown Street look real, but they’re actually painted on.\n\nNope, I have no clue either but it’s just one of the odd little touches you spot around here.\n\nA house over the road from here has a sculpture of brightly coloured pencils in its front garden, and, if you wander past the ballet school on at the right time of day you’ll be treated to the site of girls en pointe practising in what looks like garage while their mums look proudly on!"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F16.webp?alt=media&token=e3768587-e97c-4b2b-b8d9-e78d88770fe6"},{"type":"link","content":"https://www.elephantbackpacker.com.au/"}]},{"address":"Plunkett Street Public School","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.87106506065949,"longitude":151.22008725},"media":[{"type":"text","content":"# Find the Fintan Magee\nThere’s a few pieces of street art in Woolloomooloo, although not as many as you might expect considering it’s one of the grittier parts of Sydney.\n\nOne piece you might want to seek out though is Support by Fintan Magee on the wall of the Plunkett Street School.\n\nBecause it’s on school property it’s a bit tricky to get a decent picture of it. This was the closest I could manage and it involved shoving my arm through the bars of a gate – loving the additional bin detail!\n"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F17.webp?alt=media&token=05bab688-ffaf-477f-a9da-35ef9329559d"},{"type":"text","content":"Otherwise you’ll find some interesting historical murals in Bourke Street under the flyover – there’s also some vibrant tag themed art here.\n\nThe walls of the basketball courts and Woolloomooloo Playground are covered with bright murals and you’ll find some indigenous art-themed pieces at the junction of McElhone and Sydney Place.\n\nAlso, look out for this mosaic work on the PCYC building on the corner of Riley Street. It’s by famous Australian artist Byram Mansell.\n"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F17a.webp?alt=media&token=2e0d857f-e42c-4adc-bcdc-f1a0fdc0bbe1"},{"type":"link","content":"https://goo.gl/maps/m4FjV9tQ9eJR263YA"}]},{"address":"68 Sir John Young Cres","location":{"longitudeDelta":0.10218818160659443,"latitudeDelta":0.09219986310369421,"latitude":-33.87169871065971,"longitude":151.2163943},"media":[{"type":"text","content":"# Grab the Prettiest Cakes at Petal Met Sugar\nThis florist and bakery combo cater mostly for weddings, but they have a small onsite bakery and cafe with some of the prettiest cakes in Sydney.\nThey also do a high tea at weekends.\n\nYou’ll find them at Shop 7, 68 Sir John Young Cr. It’s a small space so be patient – and, if you want to try the high tea bookings are essential. They’re only open in the mornings."},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F7.webp?alt=media&token=8fa2ae1c-e18c-4a56-9c29-ab3173be4070"},{"type":"link","content":"https://www.facebook.com/petalmetsugar/"}]},{"address":"East Sydney Hotel","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.87246871066002,"longitude":151.2167676},"media":[{"type":"text","content":"# Take the Razorhurst Tour\nWhile the chi chi surroundings of the waterfront might lead you to believe that Wooloomooloo is all new and shiny, as you go inland, it’s a different story.\n\nYou’ll find row after row of tiny terraced houses, and while today these have super high price tags, back in the 1920s, Woolloomooloo, Kings Cross, Potts Point, Darlinghurst – and nearby Surry Hills, were notorious for crime, illegal booze dens, prostitution and violence.\n\nThey were known as the Razorhurst gangs, because of their pleasant habit of cutting their rivals’ faces with razors. Interestingly, two of the most notorious criminals of the time were women – brothel-keeper Tilly Devine and illegal booze peddler Kate Leigh.\nAlso note, while the violence of the Razorhurst gangs might have passed, Woolloomooloo does still have a few social issues and while it’s still very safe in comparison to what you might find in many other cities in the world, do just keep your wits about you if you start wandering the backstreets. I also keep mostly to the main roads at night."},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F12.webp?alt=media&token=beaa54c3-335c-4634-b83c-4162e3e60ba8"},{"type":"link","content":"http://www.eastsydneyhotel.com/"}]},{"address":"Cathedral Street & Palmer Street","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.872541610660065,"longitude":151.21783429999996},"media":[{"type":"text","content":"# Find the Woolloomooloo Sign\nHow many times can you walk past something and not see it? About six seems to be the answer, at least when it comes to the Woolloomooloo sign at least!\n\nI had seen pictures of it, but wasn’t quite sure where it was – and the fact that as you walk towards it, it’s hidden by a massive plant does not help!\nIf you want to find it though, it’s in the middle of the road by the junction of Palmer and Cathedral Street.\n\nBehind it is a small garden with metal cows and sheep. This was created by a TV show called Guerilla Gardens."},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F14.webp?alt=media&token=af41f191-2f3c-4c7b-99e8-3d25cc7c0175"},{"type":"link","content":"https://goo.gl/maps/cBcrWA3gcJRY7zwu8"}]},{"address":"Cathedral Street","location":{"longitudeDelta":0.10218818160659443,"latitudeDelta":0.09219986310369421,"latitude":-33.87260161066011,"longitude":151.2182203},"media":[{"type":"text","content":"# Snap a Purple Picture\nIf you’re in Sydney in late October/early November, you’re likely to hit jacaranda season, and if you do, Woolloomooloo has a couple of great locations for pictures.\nMost notably, Cathedral Street close to the junction with Dowling Street which lets you get this shot with the Sydney Tower Eye in the background.\n\nIf you want more purple pictures during your stay, check out this post on some of Sydney’s other iconic Jacaranda locations."},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F5.webp?alt=media&token=d1803328-acc2-4135-8f29-e6fc41204918"},{"type":"link","content":"https://goo.gl/maps/nCxX9nyNy39qwkEH7"}]},{"address":"114 Bourke St","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.87338381066042,"longitude":151.2184606},"media":[{"type":"text","content":"# Go Down the Rabbit Hole at Peekaboo Bar\nDescribed as where Alice in Wonderland would drink if she ended up in Sydney, this tiny bar on Bourke Street looks like it belongs back in those Tilly Devine days (without the nasty bits!).\nIt’s the perfect place to finish your day of exploring in Woolloomooloo and I can firmly recommend the pretty Bourke Street Sour which is a layered mix of whiskey with lemon, red wine and egg white!\n\nMr Differentville got lured by the word Cointreau and had a Boops Pash – the cinnamon ring round the rim makes it taste like Christmas!"},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F18.webp?alt=media&token=f20cc616-39f7-4b32-9ca1-e197831e5350"},{"type":"link","content":"https://goo.gl/maps/GR5nv91sXU1HC5Md9"}]},{"address":"Flour and Stone","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.87356966066049,"longitude":151.21546994999994},"media":[{"type":"text","content":"# Check out the Cute Eggs at Flour and Stone\nOne of Sydney’s most popular cafes, they earn their place on this list purely because they cover their boiled eggs with the cutest knitted covers.\n\nSadly, I can’t take a photo of the adorableness right now as it takes place in the part of the cafe called the Salon which is currently only open on Saturdays due to you know what! And oh heavens, the queue!!!\nThey also do super adorable cookies. Those you can get seven days a week.\n\nFind them at 43 Riley Street."},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F11.webp?alt=media&token=e9bdb85f-1e5f-4881-9e96-ccad5ebbc31c"},{"type":"link","content":"https://flourandstone.com.au/"}]},{"address":"Australian Museum of Magical Arts","location":{"longitudeDelta":0.14321712068773834,"latitudeDelta":0.09219986310369421,"latitude":-33.874956560661055,"longitude":151.21507194999998},"media":[{"type":"text","content":"# Tour the Museum of Magic\nTechnically, Woolloomooloo ends at a road called William Street and this is just across that and in Darlinghurst, but it’s really good fun so whose counting!\nThe evening tour teaches you the secrets of all those magic tricks you were amazed by when you were little."},{"type":"img","content":"https://firebasestorage.googleapis.com/v0/b/freeguides-prod.appspot.com/o/assets%2Ftours%2FMroCb9Jca2JO6TE3NSyQ%2F15.webp?alt=media&token=0484a3f0-596a-45a8-8d1f-df44cc7c50d0"},{"type":"link","content":"https://goo.gl/maps/A7ZwnpkyigDkeVVa7"}]}]