24 hours in Woolloomooloo & Potts Point

Woolloomooloo is not just a suburb famous for having eight ‘O’s in its name, but it’s an area alongside its close neighbour Potts Point that is steeped in history and culture.  Woolloomooloo’s most striking feature is the large finger wharf that extends for 400 metres into Sydney Harbour. You could be forgiven for thinking that you had stumbled on the set of Boardwalk Empire, although thankfully you don’t need to find a bootlegger to get yourself a drink around here.

Finger Wharf at Dusk

You can pack a lot into 24 hours in this area, here’s what I did.

3:00pm: Blue Hotel, Woolloomooloo: The entrance to the hotel melds original period features with a modern warehouse aesthetic. I’m warmly greeted by hotel staff before being shown to my room on the top floor of the wharf. The room features all of the mod cons you’d expect, including a king size bed, flat screen TV and iPod docking station. The bathroom is stocked with Peter Morrissey toiletries which is a nice touch. It’s time for a rest before exploring the area.

Blue Hotel, Woolloomooloo

4:36pm: After a spot of relaxing in the room, it’s time to explore the Woolloomooloo foreshore. Turn left as you leave the wharf to find the iconic Sydney pie shop, Harry’s Café de Wheels. It’s been turning out pies to feed nearby workers, locals and late night revellers alike since 1945. Beyond that are the naval yards at Garden Island. If you head up the hill, you’ll find yourself in Potts Point (it’s quite a walk) a suburb known for its art deco architecture, galleries, restaurants, bars and cafes. I’m back down the hill in time to watch the sunset from the Royal Botanic Gardens.

Vessels moored at the Wharf

Harry’s Cafe de Wheels

6:08pm: All of that walking has given me a thirst that only the nectar of the gods can fix so I wander over the road to the Tilbury Hotel. Forgetting that the nectar of the gods is actually beer, I order myself a gin martini. My partner in crime orders herself a vodka martini and we set ourselves up near one of the open fireplaces on the top floor of the pub. Our bartender suggests we try the mulled Batlow cider. He didn’t have to twist my arm very hard, and I’m glad I tried it. It’s got a hint of spice, and on a cold clear winter’s night, there’s nothing like sitting by a fire with a mug of hot and slightly alcoholic to give you the warm and fuzzies.

Upstairs bar at Tilbury Hotel

7:30pm: We cross the road and stroll up the promenade to Otto Ristorante. Our gracious host offers us a choice of seating inside or out. The heat lamps and clear night make the decision an easy one and we opt for a spot of al fresco dining. Otto is renowned for its spectacular Italian food and it doesn’t disappoint. We start with some San Danielle prosciutto and some olives before sharing a selection of pasta dishes featuring braised lamb shank, braised oxtail and lobster. Desserts and the wine list are equally spectacular. Over winter, a pop-up restaurant called The Larder will be taking over part of Otto and offering a selection of menu items under $25 and the option to BYO wine.

Pasta dish at Otto

10:23pm: While we decide to retire early this evening, there is plenty to do if you head up the road to Potts Point. If small bars are your thing, try Bootleg Bar. If you’re a cocktail fan then you can’t go past The Roosevelt for some seriously special mixology. The Piano Room is great if you like live music.

8:47am: We decide to rise and take our morning constitutional, but not before having a juice from the room service menu. Juice consumed and the cobwebs cleared from the night before, we wander through the back streets of Woolloomooloo and up to Potts Point for breakfast.

9:14am: Potts Point has some amazing laneway cafes and restaurants including Wilbur’s Place where we stop for breakfast. A delightfully cheese filled Croque Monsieur is our choice for breakfast along with an excellent espresso. The 20 seater is licenced (not that we needed to utilise that at breakfast) and also serves lunch and dinner.

Indoor dining at Wilbur’s Place

10:08am: We finish our breakfast and head to the Kings Cross Markets near the history El Alamein Fountain. The markets are held every weekend with Saturdays focusing on food stalls including cakes, organic produce, meat and ready to eat food and Sundays featuring pre-loved clothes, vintage handbags, books, shoes and jewellery.

11:23am: It’s a gorgeous sunny day so we walk down the hill to Flour & Stone, a bakery that burst onto Sydney’s culinary scene to high acclaim last year with its range of home style cakes and pastries. We collect some goodies for a picnic lunch in the Botanic Gardens before walking up to the Art Gallery of NSW.

Baked goods, Flour & Stone

11:45am: We take in some of the permanent exhibitions at the Art Gallery of NSW which you can visit free of charge. There are a range of touring exhibitions that the Gallery presents so it’s worth checking their website to see what is currently showing. Wednesday nights are also a great time to be at the Gallery as they present Art After Hours, featuring talks from guest speakers, live performance, films and a bar.

Art Gallery of NSW

Permanent Exhibitions at the Gallery

12:53pm: We head to the Palm Grove Centre in the Royal Botanic Gardensto pick up a map for a self-guided Aboriginal Heritage Tour. The tour takes in many of the plants that were used by Indigenous Australians for both food and medicinal purposes.

Wildlife in the Botanic Gardens

Botanic Gardens, Sydney

1:38pm: We finish the tour and now it’s time to enjoy our treats from Flour & Stone in the sun. We find ourselves a lawn of lush green grass and it’s time to relax.

Jeremy Bowell experienced Woolloomooloo and Potts Point as a guest of Destination NSW


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Author:Jeremy Bowell

Jeremy Bowell is the founder and editor of Taste Explorer. He also writes for InsideCuisine.com, TheGrapeHunter.com, SoBadSoGood.com and has featured in the Sydney Morning Herald's Good Living section. He is an avid connoisseur of all things food and drink related.
  • Awesome post! I loved the photos and the journal type narratives!

    I am impressed!

  • Bianca

    Great little food tour Jeremy! Some of my faves in there.

  • Christina Soong-Kroeger

    Great post – you’ve packed a lot in a very short time. btw I love the grey and hot pink in W Hotel – so sexy.

    • jezzster

      Thank you! It’s a beautiful part of Sydney

  • i love flour & stone 🙂

    • jezzster

      It’s great, isn’t it?

  • hi Jeremy – great post – did you get to check out room 10 just along from Wilburs or Coffee Tea and Me in Macleay St

    • jezzster

      I’ve been to Room 10, but not to Coffee, Tea & Me, will have to check it out!