Gnocchi with burrata at Grappa, The Rocks
The Rocks
Evening out 3 stops · 5 hrs

Gin, pasta, Guinness. In that order.

There's something to be said for a night out that doesn't require a single Uber. Frank Mac's, Grappa, and the Mercantile all sit on the same stretch of George Street, which mostly just means fewer excuses to go home early.

Frank Mac's first, for a gin in a room that's decided it's a Victorian study with slightly better lighting. Order the Mac Martini. It's expensive, there's a service charge, and you'll order a second one anyway.

Then Grappa, two minutes down the road, where the owner has a habit of greeting tables like old friends and occasionally sending over a complimentary glass of something. Nobody's quite sure why. Order the handmade pasta and don't overthink it.

Finish at the Mercantile with a Guinness, because it's Sydney's oldest Irish pub and it feels rude not to.

Gin & cocktails → handmade Italian → Irish pub nightcap
Best for A date night or a proper catch-up in Sydney's oldest streets
Best night Tue–Thu for a quieter Frank Mac's · Fri/Sat if you want it lively
Budget Roughly $135–180pp across all three stops
Dress Smart casual — Grappa and Frank Mac's both lean a little dressy
The Route Frank Mac's 1 Grappa 2 The Mercantile 3
6:00 PM
Frank Mac's
83 George St — heritage sandstone gin & cocktail bar with over 100 gins
Book ahead for weekends and live music nights
A happy hour cocktail menu runs some nights — note a service charge applies even when paying cash
OrderThe Mac Martini, or Frank's Last Drink if you're splurging — vintage vermouth, premium gin, and caviar
SaveGo Tue–Thu for a quieter room and easier seating — Fri/Sat gets loud with live music
🚶 ~2 min walk
8:00 PM
Grappa
107–109 George St — the Leichhardt Italian institution's new Rocks outpost, in the old Rockpool building
Book well ahead — busy most nights
OrderHandmade pasta (ask what's fresh that day) or the tuna carpaccio, plus something off the wood-fired oven
SaveIf your table isn't ready, ask to sit at the pizza bar while you wait — reviewers say it's half the fun
🚶 ~4 min walk
10:30 PM
The Mercantile Hotel
25 George St — Sydney's oldest Irish pub, freshly renovated with a new rooftop bar
Walk-ins fine downstairs · book ahead for the rooftop
OrderA pint of Guinness, and the Shamrock Pie if you've still got room
SaveThe ground-floor bar is free entry any night — save the rooftop for when you actually want the view
What Locals Say Ratings via Google
★★★★4.3221 reviews
Frank Mac's
Reviewers consistently praise the vintage atmosphere and attentive table service, with the gin selection and live music the most mentioned highlights — a few flag the service charge as a surprise.
★★★★4.6215 reviews
Grappa
Reviewers repeatedly call out the hospitality as the real draw, with owner Charlie Colosi personally greeting tables — the handmade pasta and wine list back it up.
★★★★4.31,980 reviews
The Mercantile Hotel
The Shamrock Pie and generous portions come up constantly, alongside praise for the newly renovated rooftop and the live Irish music that's defined the pub for generations.
What tonight costs, roughly
Frank Mac's — cocktails$30–40 pp
Grappa — Italian dinner & wine$90–120 pp
The Mercantile — a pint or two$20–25 pp
Estimated total$140–185 pp
How'd this route treat you?
Audrey likes honest feedback — good, bad, or "the rooftop cocktails weren't it."