Sydney’s Timeless Tipples – Revisiting Maybe Sammy and Cantina OK! Five Years On
Like a well-thrown boomerang, I keep coming back to Sydney—year after year, trip after trip. There’s something magnetic about this city, an irresistible pull that always brings me home to its sparkling harbour, golden beaches, and, of course, its dynamic bar scene. From timeless institutions to and fresh newcomers buzzing with character, Sydney’s nightlife evolves constantly, yet always feels familiar. Each visit uncovers something new, yet the essence of the city remains the same—welcoming, vibrant, and endlessly exciting.
Sydney’s bar scene is a fascinating blend of timeless institutions and fresh, boundary-pushing newcomers. Five years ago, I had the pleasure of visiting Maybe Sammy and Cantina OK!, two venues that, even then, stood out for their quality, hospitality, and creativity. Now, half a decade later, I returned—and to my delight, both bars are not only still standing but thriving, proving that consistency, passion, and exceptional customer care are the key ingredients for longevity in the hospitality industry.
Maybe Sammy – Old-School Glamour, Timeless Innovation
Stepping into Maybe Sammy is like entering another era—one where cocktails are an art form and service is delivered with old-world elegance. Inspired by the golden age of travel, this bar has mastered the blend of nostalgia and modern mixology. Bartenders in their signature pale pink jackets greet you with a smile, exuding charm and expertise in equal measure.
My latest visit coincided with their new menu, The Grand Maybe Sammy Hotel, a playful concept designed like a board game, inviting guests to “check in” to a world of flavours. Among the many creative cocktails I opted for the tequila based Breakfast in Bed – A tequila-based delight with almond, raspberry, strawberry, and brioche, evoking the flavours of a luxurious morning indulgence. And the Do Not Disturb – A daring milk punch with tequila, white chocolate, habanero, strawberry, and fava tonka—a sweet, creamy concoction with a spicy surprise.
As I sipped a perfectly executed Mini Irish Coffee to end the night, I realised why Maybe Sammy remains a must-visit. It’s not just the drinks, the stylish atmosphere, or the awards —it’s the way the bar makes you feel. It’s a place where hospitality is an art, where every detail is curated to perfection, and where returning after five years feels like coming home.
Cantina OK! – A Mezcal Love Story That Stands the Test of Time
On the opposite end of the spectrum is Cantina OK!, a tiny, garage-sized mezcal haven tucked away in a Sydney alley. If Maybe Sammy is about elegance and spectacle, Cantina OK! is about raw passion and authenticity. Specializing in small-batch agave spirits sourced directly from Mexican producers, this bar is proof that sometimes the smallest places leave the biggest impressions.
I first visited Cantina OK! in 2019, just months after it opened, and was instantly hooked by its intimate, standing-room-only vibe, the meticulous attention to detail, and the sheer love for mezcal that radiates from the bartenders. Walking in five years later, I was greeted like an old friend—proof that true hospitality never fades.
With a drink in hand—this time, the BONGO OK!, a mesmerizing mix of mezcal, Montenegro, umeshu, egg white, and watermelon—I marveled at how the bar still felt as vibrant as ever. From its signature house margarita served over hand-shaved ice to its ever-evolving list of agave treasures, Cantina OK! continues to be a beacon of what makes a truly special bar: passion, storytelling, and an unwavering commitment to craft.
The Secret to Longevity in the Bar Scene
If Maybe Sammy and Cantina OK! have taught me anything, it’s that true excellence in hospitality isn’t about chasing trends—it’s about creating an experience that people want to return to, again and again. Consistency, passion, and an unwavering commitment to quality are what allow great bars to not just survive but thrive.
And as Sydney’s cocktail scene continues to evolve, blending the timeless with the new, one thing is certain: the best bars aren’t just places to drink—they’re places to belong. Cheers to the past, the present, and the future of great cocktails!
Back in 2019, I wrote about my first experience with these standout bars, marvelling at their innovative cocktails and impeccable service:
