A hop, sip and a jump to Surry Hills and surrounds

It's a stormy summer's night in Sydney when I dutifully agree to the tough assignment of bar-hopping across the city, joining the dots between some of the finest places in the eastern suburbs to have a nibble and a tipple or two. My husband, Robin, is my chaperone for the night, as we tango, to and fro, across the city – from bars with beach views in Bondi to boho-heavy haunts in Surry Hills.

6.03pm @ the Bucket List Bar Eatery, Bondi

Bondi Pavilion, Queen Elizabeth Drive, 9365 4122

A beachside bar overlooking Sydney's most iconic strip of sand and sea seems the obvious place to kick off our crawl. Sharing a $10 bucket of prawns and a Pimm's with the surf a few steps away is about as near to perfection as it gets. Here, the crowd is a mix of young travellers and surfers who sit in clumps around the colourful courtyard sipping sangria or schooners of Kosciuszko Pale Ale.

6.45pm @ Bondi Hardware

39 Hall Street, 9365 7176

It's a merry hop to Bondi Hardware. Named after the previous tenant occupying the Hall Street site, Bondi Hardware honours its old blue-collar bones with exposed brickwork, beams, recycled timbers and a back-wall shrine to tools of the trades. My husband enjoys a schooner of Vale Ale while I sample the wine of the day – a $9 glass of crisp, dry Radio Boca Verdejo. As a bar snack, the mini gourmet cheeseburger sliders are a standout.

7.25pm @ El Topo, Bondi Junction

The Eastern Hotel, 500 Oxford Street, 8383 5959

“Onward and upward!” trumpets my husband as we hustle up the hill to El Topo, the new slick Mexican joint on the rooftop of the Eastern Hotel. The place is pumping out pop tunes, has buckets of ambience and great service and is a magnet for a mixed crowd of fashionistas and foreigners. We agree to bartender Brett Harris's assertion that a shot of Tapatio tequila is compulsory. “It will knock your socks off,” he says. It does. We also scoff down a few tacos . . . all in the name of research, of course.

8.05pm @ Hinky Dinks, Darlinghurst

185 Darlinghurst Road, 8084 6379

Hinky Dinks is like a 1950s time capsule, with black-and-white chequered flooring, vintage red bar stools and cosy booths. It's Wild Wing Wednesday so my wingman orders a few $1 chicken wings, with a glass of Tinja Riesling. Adventurous types should try an El Mexicano – a chipotle-infused cocktail with sweet vermouth, Campari, chocolate bitters, and soda served on the rocks with a wedge of blood orange.

8.45pm @ Bootleg Bar & Italian Food, Potts Point

175 Victoria Street, 9361 3884

We've missed the daily happy hour but are feeling perky when we slice through the sleaze of Kings Cross and into Bootleg Bar. Bartender Owen Lyons mashes up his signature cocktail: a Bloody Martini made with home-made consomme. The quality of the food and drink here is evidenced by its popularity; the place is packed. Try the pastrami, which owner and chef Rob Gal brines and smokes on-site himself.

9.30pm @ Bottleneck Bar & Eatery, Darlinghurst

229 Darlinghurst Road, 0422 263 226

Word on the street is that it's the unofficial opening night at the Bottleneck Bar & Eatery, an offshoot of Eau de Vie, so we feel obliged to check it out. Here, it's all about the (meat)balls, boutique brews and Bloody Marys. As well as creating cracking cocktails, the pocket-size space is helping to alleviate the bottleneck queues curling out the door at Eau de Vie.

10.05pm @ the Hazy Rose, Darlinghurst

83 Stanley Street, 9357 5036

Hazy Rose is dangerously decadent, with a 1920s bordello-like feel. Our moustachioed bartender Brendan Keown keeps the conversation and cocktails flowing. His "riff on the Mint Julep" is, my husband says, “like a kick up the backside”.

10.30pm @ Love, Tilly Devine, Darlinghurst

91 Crown Lane, 9326 9297

Hidden down a back alley in Darlinghurst is this dinky little Brooklyn-style bar named after the former east Sydney brothel madam, which, tonight, is crammed with a clued-up crowd of young city workers. Hastings River rock oysters, opened to order, are $3.50 each and pair well with a crisp glass of riesling – which the wine list states is “the best drink in this bar/the best drink in any bar".

10.55pm @ Red Lily Cocktail Bar, Darlinghurst

60 Crown Lane, 9698 4355

A hop, skip and a jump away is Red Lily, the sort of place you end up by happy accident and don't want to leave. Although it feels as if we gatecrashed an intimate party, we receive a warm welcome at this old-Saigon-styled bar, which backs on to the latest Nguyen family restaurant, Red Lantern on Riley. The chilli-salted squid is reason enough to visit. Add to the mix some soft Asian vintage soul, Vietnamese beers, classic cocktails, lightning-quick service and fabulous Asian street food and you have one seriously seductive small bar.

11.30pm @ Shady Pines Saloon, Darlinghurst

256 Crown Street, no phone

After a quick cab ride across town, we arrive at a nondescript building, push past a white curtain and stumble down some stairs into what appears to be an urban lumberjack convention: there are beards and check shirts everywhere. “I have beard envy,” my husband says. As well as keeping the art of taxidermy alive and well, Shady Pines is big and dirty and brash and raucous and right out of an American book of cliches. As the country and western music is turned up, so is the vibe. And according to my hastily scrawled notes, we loved it! Ask the bartender to whip you up an Old Pal – equal parts whisky, sweet vermouth and Campari.

11.50pm @ Tio's, Surry Hills

14 Foster Street, no phone

Before we turn into pumpkins, we detour to Tio's, where it's all about the tequila, tinnies and tacos. It's close to closing time, but our tattooed bartender makes time to fizz and swizzle up our last drink for the night, the El Roberto Especial – tequila with fresh apple juice, mint, coriander, parsley, lime and cucumber. This Guatemalan-themed small bar has taken inspiration from Shady Pines and run with it: it feels like a cluttered and eclectic Latin-flavoured emporium dedicated to fun. Wearing stupid grins, we toast to a night of being wild and reckless, knock back our last bevvy and stumble to a cab.