34 Ways in Two Days: A Gentleman’s Guide to the Ultimate Weekend in Sydney Aiden Darling Harbour

Hotel in Sydney
Aiden Darling Harbour

34 Ways in Two Days: A Gentleman’s Guide to the Ultimate Weekend in Sydney

Looking to get off the grid and bond with your buddies on a boys weekend away? Or simply need some time out on your own solo man holiday? Take inspiration from this two-day itinerary packed with plenty to keep a guy going.



Whether it’s a milestone birthday celebration, bucks weekend, or filling in some downtime on your next business trip to the city, there’s plenty to see and do in Sydney for a worldy gentleman like you.


If you want a mix of outdoor adventure, great bars and pubs, excellent eats and a bit of culture, then look no further than the inner-city village of Pyrmont. Everything you need for 48 hours of fun with your best mates can be found here for your one-night getaway or multi-day staycation.   


And the best bit? Everything you need to make for a memorable holiday is within walking distance. No designated driving, organizing Ubers or forking out for stretch limos required.


Here’s 34 different (and sometimes alternative) ways to get the most out of your trip away.


Day 1


Breakfast is the most important meal of the day so make it count. Start with a wholesome breakfast at our Wayfarer’s Bar & Café with dishes like prawn and chorizo ​​scrambled eggs or a hearty honey-smoked bacon and egg sandwich with sriracha mayo. Or head out to nearby Harris Street to grab a fresh takeaway pastry and coffee from little artisan PiOiK Bakery (tip: you may need to line up, it can get busy!).


After a feed, take a flat 20-minute stroll around Blackwattle Bay to Paddle Pirates in Glebe, to gear up and embark on a half-day kayaking adventure around Sydney Harbour. Keep your eye out for seals, penguins and white bellied sea eagles as You tour the bays and harbor islands of Goat and Fort Denison, guided by an expert sea kayaker.


Worked up an appetite? Stop by the iconic Sydney Fish Market, a must-visit in the area for the freshest fish and chips or a sprawling seafood platter, enjoyed on the wharf overlooking the water.




Feel and look the part of a man on a mission: head to Clippers N Whisky for a trim and a dram to set the tone for the rest of the weekend. Be greeted with a complimentary drink of your choice (whisky, gin or vodka perhaps?) before enjoying a high-end barber and groom session.


Carry on into the afternoon on a leisurely pub crawl around Pyrmont’s historic watering holes, sipping one of 34 craft beers on tap up on the sunny rooftop at The Quarryman’s, or nurse a pint at the village’s oldest pub, the recently renovated Terminus Hotel.





After a shower and a refresh back at the hotel, sneak in a cheeky pre-dinner wine and bar snack at Wayfarer’s before walking to smart and sultry Sokyo Bar for one of their signature cocktails with a Japanese twist – our pick is the Lychee Sgroppino, a mix of yuzushu, lychee sorbet, bergamot liqueur and Champagne.


Dining out? Treat yourself to a memorable degustation at one of Sydney’s best waterside restaurants, LuMi, enjoying artfully-plated dish after dish matched with wines, while perched on the wharf overlooking the harbour. Or for something more casual, enjoy a pub feed at the locals’ favourite Gallon, before heading to The Star casino for a flutter.



Then it’s just a block’s walk back to the hotel to rest your weary head, embracing all the elements of Aiden Darling Harbour’s Sleep Ritual Program – from your choice of pillow to blackout blinds. And if you are in need of hydration, you can drink your fill of complimentary Moda sparkling or still water before hitting the hay.


Day 2


After a great night’s sleep and a blast in your singworthy shower, kick off your day early with a fishing adventure with Deep Blue Charters, picking you up from one of two locations in Pyrmont for a morning out on the productive reefs and fish feeding grounds a few nautical miles out to sea. You might even catch a few dolphins and whales!


Or take the opportunity to enjoy a sleep in and later dabble in a bit of wharf fishing at one of several popular spots around Pyrmont, picking up fishing gear and tackle from Net and Tackle Sales at Sydney Fish Market.



If fishing isn’t your thing and you’re a man of the land instead, get yourself an electric bike from Sydney Electric Bikes and take a self-guided tour of the weird and wonderful street art dotted around Pyrmont and Darling Harbour. Be sure to fuel up on an aromatic coffee along the way – there’s no shortage of options for the perfect brew in the area.


Stretch your legs further and take a ride along the promenades and wharves running from the Anzac Bridge, across the Pyrmont Bridge and all the way around to Barangaroo Reserve – a sprawling six-hectare parkland with views back down to Pyrmont and across to the Sydney Harbour Bridge.

Hungry after all that exercise? Scoop up a chargrilled chicken and chips feast from Birdie’s Rotisserie to enjoy picnic-style by the harbour at one of the many great green spaces in the area. Or park your bike in Pirrama Park and indulge in the crab ravioli in a seafood bisque at the harbourfront Zebra Lounge.




Keen to keep the adrenaline pumping? Wander down to Darling Harbour‘s Harbourside, just a few minutes’ walk from the hotel, to face off in a laser tag battle at Kingpin, or channel your inner Tom Hanks and learn to fly a Boeing 777 at Flight Experience.


To mark the occasion, literally, head to Darling Square and step inside the professional studio of world renowned tattoo artist Todd Bailey at Thirteen Feet Tattoo.


Or head in the opposite direction and into the Australian National Maritime Museum, just across the road from the hotel, to lose yourself among the many nautical exhibits and activities on offer, from 14 different vessels to a 3D cinema.



Can’t get enough of Sydney’s beautiful harbour? Head back out on the water for a luxury Sydney By Sail twilight cruise, sipping BYO beverages while the sun sets over the city, snapping a few pics as you sail underneath by the Sydney Harbour Bridge (and get those pics straight onto Instagram).



Back on dry land, go for an alfresco beer or two at Bucket Boys and a casual dinner of noodles, ramen, bao or burgers at one of the 40+ eateries at Darling Square or tackle a full rack of ribs (and a jacket potato?) at Hurricanes.


Or head back to Harris Street in Pyrmont for a more upmarket dinner on the terrace at Bar Clementine or new Japanese restaurant Nodaya choosing from a full range of Japanese whiskey and sake. For a more casual dining experience don’t look past Umami Dojo, a husband and wife run ramen house, whose signature siphoned ramen is a feast for the eyes and the stomach.



Seek out a nightcap at one of Pyrmont’s newest bars The Laneway Pyrmont, or local staple Gallon wine bar, before retreating back to your room at the hotel.


Not ready for bed yet? Stay up late streaming Netflix in your room for free via the hotel’s super speedy wi-fi with complimentary chromecasting in your room.


Sleeping arrangements

Gather your buddies together and stay at Aiden Darling Harbour, choosing from a range of different room types, from The Exhibitionist (perfect for when you just need a place to lay your head) and The Good Twin (with two single beds, so twice the fun!), to the top floor The Balcony rooms with oodles of space and a private balcony overlooking the city. Some rooms are also interconnecting, joining together two adjacent rooms.


Take a look at our current special offers and packages here.



Bookings & activities

Our team of hosts would be delighted to assist with creating and booking a tailored itinerary of local activities for your trip. Get in touch with questions and requests, as well as other insider tips and suggestions on what to see and do in Sydney.


Please note, businesses and tour operators may not be in operation during pandemic lockdowns, and/or may have adjusted opening hours during special event periods and major holidays. Some activities require pre-booking and are subject to availability. It’s always best to check first!




A gift that keeps on giving?

Looking to treat a special guy in your life to a mancation? Perhaps as an engagement present, head wetting for a first baby, thank you gift or a romantic gesture?


Take the guesswork out of the equation with an Aiden Darling Harbor gift voucher. Purchase here .



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