When globally acclaimed cocktail bar Maybe Sammy opened its doors in The Rocks, it helped spark the transformation of this historic harbourside precinct in the very heart of Sydney into a sophisticated nightlife destination. Here, Maybe Sammy co-owner Stefano Catino takes us on a tour of his favourite bars, restaurants and hotels in The Rocks and its close neighbour, Circular Quay. 

Embrace history — and aperitivo highballs 

The site of the oldest European settlement in Sydney, The Rocks has long drawn visitors admiring the imposing colonial-era sandstone buildings lining its hilly streets. The heritage precinct and neighbouring Circular Quay are popular destinations all year round, and attract big crowds for events such as Vivid Sydney, an annual festival of light and creativity that runs from late May to mid-June; and the concerts and fireworks of New Year’s Eve and Australia Day.  

In recent years, though, a new global drawcard has emerged in The Rocks: Maybe Sammy. This innovative cocktail bar, tucked away in the block between the Four Seasons Hotel Sydney and Shangri-La Sydney, has been named as one of The World’s 50 Best Bars for the past four years running, and picked up the Best International Bar Team award at the 2022 Spirited Awards.  

Maybe Sammy doesn’t take bookings, so come early to secure your seat and discover the appeal as smartly dressed, charismatic bartenders whip up a creative concoction for you to enjoy in a setting oozing 1950s-style glamour. Don’t be too disappointed if you can’t get in right away: there are plenty of other great bars in the area, says Stefano. “There’s been a revolution in The Rocks, with a lot of good operators opening. You have Doss House down the road, which is a beautiful whisky bar, and Hickson House — they distil their own gin and vodka there and they have a beautiful bar. They make a gin [Hickson Road Australian Dry Gin] that’s amazing; we use it at Maybe Sammy. And Alice is a sexy underground bar; it’s super cool and the drinks are amazing.” 

Feel spoilt for choice 

Stefano says his team will recommend nearby bars when they have to reluctantly turn away guests from a packed Maybe Sammy. “I send people to Double Deuce Lounge, it’s a nice little place, super cool; and I send people to Grain, the bar at the Four Seasons. [Maybe Sammy’s sister bar] Dean & Nancy on 22 is very close by, so we send people there, too.” 

Grain, the Four Seasons Hotel Sydney’s ground-floor cocktail bar, is a favourite of the Maybe Sammy staff: “They go on their breaks to Grain: the guys there are very good friends. The guys come up on their breaks, and we go down there on our breaks.” 

And if Stefano wants to take visitors to a bar with great views, he’ll head to Henry Deane at Hotel Palisade, high above The Rocks at Millers Point. “When you arrive there, it looks like an Aussie pub,” he says, “but when you take the lift and it opens up to this spectacular view of Sydney you don’t expect…I like Henry Deane for that wow factor. That’s definitely one of the places where I usually take people.” 

Savour Italian flavours 

After cocktail hour at Maybe Sammy or a nearby bar, there are plenty of options for dinner in the neighbourhood. Stefano, who grew up in the port town of Vernazza on the Italian Riviera, suggests heading to Hinchcliff House, which offers four levels of restaurants and bars in a former wool store behind Customs House at Circular Quay, to dine at Italian-influenced Grana. “I’ve had lunch and dinner there several times and it’s amazing. Good produce — they make their own flour; they have a very good head chef and a very good team. The food has always been top notch.”  

Hinchcliff House’s Sicilian-themed Apollonia basement bar is another option for pre-dinner drinks. “That’s a good cocktail bar as well, very good negronis. It’s funny, Apollonia was the wife of Michael Corleone in The Godfather — it’s a good story, so for an Italian like me, it’s very tempting to go there.”  

And if you want to keep the Italian vibe going, Stefano recommends the Tuscan-style steak restaurant Bistecca, a three-minute walk from Maybe Sammy on Dalley Street: “It’s the best Italian steak in Sydney.” 

Dazzle your friends, or your date 

To celebrate modern Australian cuisine in an unforgettable setting, Stefano suggests the fine-dining restaurants Quay in The Rocks, Aria or Bennelong at the Sydney Opera House: “They’re the top three places where you’d take someone for a wow factor, and Cafe Sydney [on top of Customs House at Circular Quay], it has a wow factor too, with a very beautiful view of Sydney. I went to Bennelong for one of my best friends’ wedding. It’s always beautiful, and the setting in the Opera House is spectacular.” 

Organising a restaurant in The Rocks for a date? Stefano’s tip is the award-winning contemporary Japanese restaurant Saké, a five-minute walk away on Argyle Street. “Maybe Sammy opens at 4.30pm; I love that time before the sun sets, I love the light inside the venue. It’s a beautiful time to have a drink, then you move on to Saké. A lot of people come in and when I ask them where they’re going next, they say: ‘We’re going for a date night at Saké.’” 

Venture deep into the night 

When it comes to recommending a place to stay in The Rocks, Stefano will steer visiting friends to one of the luxury hotels lining the harbour. “For the best views, you have the Four Seasons and the Shangri-La. When friends come, my favourite one is the Park Hyatt Sydney — that’s the best. Pier One [Pier One Sydney Harbour, a short walk from The Rocks to nearby Walsh Bay] is beautiful too.” 

And when Maybe Sammy has served its last expertly crafted cocktail for the night, where do the staff go to wind down over a drink? “Lately, they’re tending to all go home, because we’ve been working very hard,” Stefano says with a laugh. “There are a couple of pubs that are open late, like the Fortune of War, one of the oldest pubs in Sydney — it’s always good to go there and get a cold beer.”