Sydney doesn’t shout about its best bars. You find them down an unmarked alleyway, or behind a door in The Rocks that you’d walk straight past in daylight. On this trip I had two names on my list: one bar that has made The World’s 50 Best Bars seven years in a row, and another that’s been a whisky lover’s secret for years.
I visited Baxter Inn on my first night in Sydney and Maybe Sammy the next evening. They are very different experiences, which is exactly what I like about exploring a city through its bars. Like my Delhi and Jaipur guides, this is my honest take from the perspective of a solo traveller.
BAXTER INN
📍 Clarence Street, CBD
Baxter Inn was the bar I was particularly curious about. It has the reputation, the awards and, perhaps most importantly, a serious obsession with whiskey.
Vibe : You walk down an unmarked laneway off Clarence Street, then down some stairs into a basement, and suddenly you’re in a dimly lit, narrow room with a bar that runs almost the whole length. Behind it is a wall of whisky, with more than 800 bottles, lit up like a library. Old-school music plays, and bowl of pretzels.
My Experience: I went on a Friday late evening, and got a counter seat. It was as busy as it could get with young and old, those who were looking for a drink before hitting the club. A patron next to me was have an interesting conversation and that’s when I knew the bartenders knew their whisky list inside out. If you’re unsure, tell them what you like and let them guide you. That’s the best way to enjoy this bar.
I had a Old Fashioned – it was perfectly done with the bitters
In person, it didn’t come together for me, it’s a bar with plenty of character but a little less wow. It’s tightly packed, and once the after-work crowd arrives it gets loud and standing-room only, so lingering over a dram isn’t easy. If you’re not a whisky drinker, a lot of the magic will pass you by.
Will I visit again: Probably not. I wouldn’t go out of my way, but I wouldn’t talk a whisky lover out of trying it.
MAYBE SAMMY
📍 The Rocks, Sydney
Maybe Sammy is a very different proposition from Baxter Inn. Where Baxter Inn leans heavily into its whiskey-bar identity, Maybe Sammy is much more about the performance, energy and hospitality of the cocktail experience – Think velvet, soft pink and gold light, and bartenders in sharp suits who look like they stepped off a film set. It’s theatrical, and it knows it. You’ll see bubbles, flourishes and drinks presented like a small performance.
Vibe: Stylish, lively and polished. There is a sense that the bartenders are part of the show, but the atmosphere still feels welcoming rather than intimidating.
My Experience: I enjoyed the energy here. It is the kind of place where the room feels alive and the interaction with the bar team becomes part of the evening. For a solo traveller, that can make a big difference — you don’t necessarily need a group around you to feel involved.
It was also a good contrast to Baxter Inn. Instead of the focus being primarily on the bottle collection and the hidden-bar experience, Maybe Sammy puts more emphasis on cocktails, service and the overall performance.
Will I visit again: Yes. I would return to Maybe Sammy when I want a more energetic cocktail-bar experience.
Overall
What stood out to me about these two Sydney bars was how different they were despite both being destinations for serious drinkers.
Both work for a solo night out, which is something I always pay attention to when travelling. A good bar shouldn’t make you feel like you’re missing someone at the table.
Sydney definitely deserves a longer bar crawl. These were only two stops, but they gave me a good introduction to two very different sides of the city’s cocktail culture.