The Situation

Jahan (32) and Luca (30) came to us about three months out. Both grooms-to-be, both living in NYC, both college friends — and they wanted to do a joint bachelor party. Great idea in theory, until you add two different friend groups on two different coasts.

One group in LA. One group in NYC. Twenty guys total. Nobody had been to Montréal before. They'd done the Vegas/Miami/Tulum circuit already and wanted something different, so they landed on the destination. Beyond that — nothing was figured out.

Here's the part most people don't realize until it's too late: 20 guys is massive by Montréal standards. The city isn't built for large tourist groups the way Vegas is — it's metropolitan, more like New York. Restaurants, clubs, and bars run smaller rooms. Without connections, a group this size literally won't get in anywhere. See our large-group playbook for the full picture.

Before the breakdown, here's the weekend the way the group saw it.

The Brief

They hopped on a quick call with us and laid out where they were stuck. We ran a short consult to figure out what kind of guys they are, what they're into, and what matters most — then put together a plan as a starting point.

That's what we do for every client. We use years of experience planning thousands of bachelor parties to hand groups a starting point they can take to the crew. Because every bachelor party really comes down to the same three questions:

Where are we going? What are we doing? How much does it cost?

We can have all of that solved in literally a matter of minutes. Now here's the thing — while everyone wants to have a good time, nobody very often understands what that actually entails, especially when you factor in group dynamics. Everyone wants to deliver the best weekend for their friends, but we have to drill down a little to make that happen.

After a few back-and-forths, here's what we knew about Jahan and Luca's group:

The Stay

This is the most overlooked part of any bachelor party. The core problem: there are almost no properties in a good location with enough bedrooms to accommodate a large group. We have exclusive access to two side-by-side downtown bed-and-breakfasts — Luxury Mansion and Bachelor Pad. The group booked all 10 bedrooms across both properties, all confirmed before anyone landed, and it made the 20-person setup feel effortless.

Day 1 — Arrival

Check-in to their rooms, then a kick-off party with a beer pong tournament and some "entertainment" to set the tone. Dinner was Schwartz's catering — a Connected Montréal exclusive you're not getting on your own. The night wound down with bar-hopping and late hangs back at the spot.

Day 2 — The Full Send

Daytime was curling — gets competitive fast and is way more fun than anyone expects. Dinner was a private BBQ chef cooking tomahawk steaks on-site, so no reservations, everyone eating together. Night was a VIP table at the best nightclub in the city with bottles already paid. Show up and enjoy.

Day 3 — The Finale

Morning: hungover wake-up, private chef breakfast catering on-site to bring everyone back. Afternoon we kept open — we knew the guys would be hurting and left room to recover and explore the city. Closer was a supper club experience — dinner that transitions into a full-blown club as the night goes on, bottles already handled. Hands down the best way to end a Montréal weekend.

The Results

Final per-person cost: under $1,700 — accommodations, food, drinks, and entertainment all in. Twenty guys, three days, 10 bedrooms across two downtown properties, Schwartz's catering, private BBQ, curling, VIP nightclub, supper club finale. Every reservation booked, every detail handled, every dollar collected before the weekend started.

Cheaper and easier than any Vegas or Miami trip these guys had done before — and a better weekend out of it.

Hear It From the Group

Here's the weekend in motion — shot and edited from the group's own footage.

And the written word: Luca Calzoni left a five-star Google review the same week. Here it is, unedited.

If you want the same thing — zero logistics, top-tier food, VIP access, and a crew that's been through every edge case — browse our weekend packages or read the Montréal bachelor party guide to see what a full weekend looks like.