Sydney Whiskey Weekender. A barber, a bookmaker & seamstress walk into bar

An exclusive weekend visit to hidden bars, world‑class whisky, speakeasy chatter, distillery and cuisine magic in colonial and modern Sydney

The Sydney Whiskey Weekender — Where Your Story Begins

In the heart of Sydney’s CBD, where sandstone meets skyline and secrets hide behind unmarked doors, a tale of intrigue is about to unfold. A Barber with wit as sharp as his shears, a Bootmaker with a taste for trouble and fine spirits, and a Seamstress who stitches together the city’s hidden stories — three unlikely companions bound by curiosity, craft, and the call of a good dram.

Their adventure begins below…
But first, let’s talk about your weekend.

A four‑hour immersion at the Sydney Whisky Show, featuring 120 whiskies from around the world. Cocktails, tastings, tours, hidden bars, English taverns, unforgettable food, and a cast of characters (including you) ready to make memories.

This is the kind of weekend you’ll talk about for years.

• Two nights in a 4‑star Sydney CBD hotel
• One ticket to the Sydney Spirits Festival (200+ spirits, unlimited tastings)
• Branded tasting glass
• Coffee & cannoli overlooking the Sydney Opera House
• Seven venues: 5 bars, 1 pub, 1 English tavern
• Distillery tour + tasting paddle
• Bottomless brunch
• English Sunday roast
• Welcome dinner with your hosts
• Snacks & water all weekend
• Transport between hotel and venues

FRIDAY

2:00 PM — Check‑in and settle into your 4‑star hotel.
7:00 PM — Welcome dinner & dessert at The Lord Nelson Brewery Hotel, Australia’s oldest pub brewery.
10:00 PM — Bar hop begins at The Old Bootmaker with a signature cocktail.

SATURDAY

Morning — Free time for breakfast.

11:00 AM — Bottomless Gin Brunch at Hickson House
A feast of olives, focaccia, wagyu, barramundi, salads, fries, and bottomless G&Ts, wines, and beers.

2:00 PM — Hickson House Distillery Tour
Learn the craft, taste the spirit, and wander the historic Rocks afterwards — or sneak in a cheeky nanna nap.

4:00 PM — Time to dress for the show.

6:00 PM – 9:00 PM — Sydney Whisky Show
120 whiskies. Global brands. Rare pours. Unlimited tastings.
Past years have featured some of the biggest names in Australian spirits.
This year’s lineup remains a mystery… for now.
But trust us — the reveal will be worth the wait.

9:30 PM — The Barber Shop, Australia’s best gin bar.
11:00 PM — The Fabric Storehouse, Sydney’s original speakeasy whiskey den.
1:00 AM — Nightcap shooter. Your choices. Your consequences.

SUNDAY

11:00 AM — Late checkout.
11:30 AM — Sunday Roast at The Duke of Clarence — roast main, dessert, and your choice of Bloody Mary or Irish Coffee.
2:00 PM — Tour concludes… but your story doesn’t.

The Barber

A master of detail with laughter that cuts through the night. A familiar face in every whisky bar, charming, rugged, and always in the know. Whiskey liquer isn’t just his drink — it’s his language.

The Bootmaker

A straight on ice whiskey‑loving rebel with a hip flask full of stories. Rough around the edges, irresistible to trouble, and loyal to the core. His boots have walked more back‑alley bars than most people know exist.

The Seamstress

A whisky cocktail ‑drinking mastermind of secrets and disguises. Her fingers stitch stories, her network whispers truths, and her smile lights up every hidden room. If something needs doing, she knows who to call.

Together, they weave a tapestry of mischief, discovery, and late‑night magic — and they’ve saved a place for you.

As the sun dips behind The Rocks, the trio steps into the night — the Barber adjusting his cuffs, the Bootmaker tightening his flask strap, the Seamstress smoothing her dress with a knowing smile.

They’ve danced through hidden doorways, traded secrets with distillers, tasted spirits older than legends, and wandered cobblestone lanes where history lingers like perfume.

But this isn’t just their story.
It’s yours waiting to happen.

The Barber raises his glass with a grin that suggests he knows what’s coming.
The Bootmaker nudges you, already plotting mischief.
The Seamstress leans in and whispers, “Adventures like this aren’t meant to be watched. They’re meant to be lived.”

The door swings open.
The invitation glows.
Your seat is waiting.
Your glass is waiting.
Your story begins the moment you say yes.

• Payment in full at time of booking
• Show tickets will sell out — secure your place early
• Already have show tickets? Chat with us about joining the tour

We encourage responsible drinking. Spittoons are available at tastings. Water and food are provided throughout the weekend. You are not expected — nor encouraged — to drink everything offered. Venue entry is at the discretion of each establishment. Unruly guests will be escorted back to the hotel. Tour is 18+.