Bootlegger Montreal: Whiskey Tasting at Your Own Place

Montreal is known for its wild nightlife, sexy energy, and unforgettable bachelor parties. But what if we told you there’s a hidden gem in the heart of the city that offers something more refined... more exclusive... and definitely more dangerous in all the right ways?

Enter Bar Bootlegger, a speakeasy-style bar and private event destination that combines prohibition-era vibes with world-class spirits, curated tastings, and custom cocktail experiences. Whether you're planning a bachelor party, private celebration, corporate mixer, or something that deserves a little mystery, Bootlegger might just be your best-kept secret.

In this post, we’re breaking down why Bootlegger is one of Montreal’s hottest private event venues, how to elevate your night with tasting experiences and bar services, and how our topless waitresses and private showgirls can turn your Bootlegger event into a night your crew won’t forget.

A Hidden Speakeasy Vibe in the Heart of Montreal

Bootlegger isn’t just another bar—it’s an experience. From the moment you enter, the space wraps you in warm, dark wood, vintage fixtures, and the low hum of jazz and conversation. The lighting is soft, the spirits are top-shelf, and the vibe? Sophisticated, sultry, and a little bit secretive.

This isn’t the kind of place where you shout over club music. It’s where you sip rare whiskies, flirt with elegance, and toast to unforgettable nights.

What Makes Bootlegger Ideal for Private Parties?

1. Private Tasting Experiences

If your group is made up of whiskey nerds, tequila lovers, or simply guys who enjoy sipping something smooth—Bootlegger offers private tasting sessions led by expert sommeliers or spirit specialists.

You can choose from:

• Whisky

• Tequila

• Cognac

• Absinthe

During these tastings, your guests will learn how to nose, taste, and evaluate each spirit while diving into its history, flavor notes, and ideal pairings. It’s the perfect mix of education and indulgence.

Duration: 1 to 4 hours
Includes: Tasting specialist, curated spirit menu, tasting accessories
Perfect for: Bachelor parties, birthdays, client events, or high-end friend groups

2. Walk-Up Tasting Bars

Want something more casual? Bootlegger also offers tasting counters—interactive stations where guests can sample spirits and chat one-on-one with an expert.

Perfect for adding flavor (literally) to:

• House parties

• Rooftop lounges

• Chalet rentals

• Private poker nights

Rate: $90/hour (spirits and glassware not included)

Pair this with a topless waitress to serve the shots, and you’ve got a whole experience—social, classy, and just the right amount of spicy.

Go Beyond the Bar: Add Custom Cocktails

Don’t want just straight spirits? Bootlegger offers full-service cocktail bars using:

• Housemade syrups and bitters

• Fresh-pressed juices

• Botanical infusions

• Locally sourced mixers

Their team will design a menu based on your preferences. Whether you're into citrusy tequila cocktails, smoky mezcal, or a twist on the Old Fashioned, your drinks will be as memorable as the entertainment.

Oysters and Cigars? They’ve Got That Too

If your group’s looking for even more flavor and flair, Bootlegger also offers:

Oyster Bar Service

• Minimum 100 oysters

• Includes sauces and full prep setup

• Great for summer bachelor nights and VIP birthday events

Cigar Tastings

• Curated premium cigars

• Short tasting experience (about 45 minutes)

• Ask us about pairing this with a showgirl for ultimate luxury energy

Mixing Bootlegger With Our Entertainment

Here’s where we come in.

Booking Bootlegger gives you the drinks. We bring the vibe and energy.

Combine their experience with:

• Topless waitresses serving drinks and hosting games

• Private strip shows for the bachelor

• Lingerie-clad party hosts who keep the energy sexy and smooth

We’ve done countless parties with Bootlegger. The vibe is ideal for intimate private shows, cheeky group fun, and everything in between.

Example Party Packages

The Sophisticated Bachelor Party

• Private whisky tasting

• Two topless waitresses serving and chatting

• Raunchy show stripping down the bachelor

• Optional cigar station to end the night

The F1 Celebration Package

• Cocktail tasting for the crew

• Duo strip show with themed costumes (cops, school girl, etc)

• Shot rounds, party games, and topless servers

• Perfect for guests visiting from out of town

Corporate But Naughty

• Mezcal and tequila bar

• Lingerie-clad cocktail servers

• No full nudity—just flirty, fun, and tasteful for team bonding

Signature Cocktails and Pairings: Take It Further

If you're booking a tasting or custom cocktail bar at Bootlegger, why not turn it into a full-on tasting experience with curated pairings?

Here’s how to make it unforgettable:

Tequila and Tastes
Pair premium tequilas with citrusy bites, spicy snacks, or even mini tacos. Add one of our topless waitresses in a Day-of-the-Dead themed outfit, and suddenly it’s not just a tasting—it’s a fiesta.

Whisky and Chocolate
Bring out the rich notes of aged whisky with handcrafted chocolate pairings. We’ve seen groups turn this into a cheeky “taste test” game led by one of our entertainers.

Absinthe and Mystery
Absinthe isn’t for the faint of heart, and that’s the point. Bring a little mystique to the party with a Moulin Rouge-style dancer or burlesque show that channels vintage Parisian glam.

If you're unsure how to design a pairing experience, Bootlegger’s staff can help craft something truly one-of-a-kind. Just let us know the vibe—luxury, playful, seductive—and we’ll sync up the entertainment.

Behind the Scenes: Bootlegger’s Creative Team

What makes Bootlegger such a standout venue is the detail behind the scenes. Every event is shaped by passionate mixologists, tasting guides, and designers who actually care about your experience—not just pushing drinks.

You’re not getting cookie-cutter bar staff here. You’re getting people who know how to craft a moment. The lighting, the decor, the playlist—it’s all intentional. And when our girls show up, it blends seamlessly.

We've worked with Bootlegger's team on dozens of events. They’re professional, adaptable, and always respectful of our staff. That collaboration means your night won’t feel disjointed. The vibe stays fluid, sexy, and smooth from start to finish.

Designing the Perfect Party Timeline

Worried about how to structure your night so it doesn’t peak too early (or too late)? Here’s a proven timeline we recommend:

7:00 PM — Arrival and Drinks
Let guests ease in. Low music, light drinks.

7:30 PM — Spirit Tasting Begins
Guided tasting begins. Keep it educational but social.

8:30 PM — Entertainers Arrive
Topless waitresses or lingerie servers begin pouring shots and hosting games.

9:00 PM — Private Show
A quick striptease, lap dance, or burlesque number keeps energy high.

9:30 PM — Cigars and Cocktails
Transition into slower conversation or a second cocktail menu.

10:00 PM Onward — Let the Party Flow
Freestyle fun—let your guests take it from there.

What You Should Know Before Booking

• Travel fees and setup costs may apply

• You’ll need to provide or pre-arrange spirits for tastings

• We recommend booking 2–4 weeks in advance

• Our entertainers are professional, friendly, and classy—not clubby or pushy

Final Thoughts: Why This Combo Works So Well

Montreal’s nightlife is next level—but too many parties fall into the same routine: bar, club, back home, forgettable.

With Bootlegger and our team combined, you get:

• Your private space with speakeasy elegance

• World-class cocktails and tastings

• Stunning women who know how to engage and entertain

• A party that feels personalized, exclusive, and elevated

Bachelor parties don’t have to be loud and sloppy. They can be smooth, sexy, and unforgettable. That’s exactly what this combo delivers.

Ready to Book?

Visit barbootlegger.com to check out the venue.

Then contact us at +1 438-367-7843 to add topless waitresses, strip shows, or curated party extras.

We’ll help you:

• Choose the right girls

• Plan the flow of the night

• Match the theme to your group

• Coordinate seamlessly with Bootlegger’s staff

Let’s build a night your crew will never forget.

MTL Bachelor Waitress x Bootlegger
Where luxury meets debauchery.
www.mtlbachelorwaitress.com