I used to know a few lounges in Montreal. Seems like the clientele is getting way younger as I get older so I kinda lost interest in places filled with 18-25 year olds and extremly loud music.
Also, since covid, a few bars have closed down so I've had to start searching all over again -- which has been a blast so far!
I look forward to others chiming in with a few reccos, but in the mean time here is my recipe to a fun night:
Marcus (Four seasons hotel downtow)
They have an nice lounge area as well as a fine dining experience (currently my favorite in Montreal). I often start off with drinks at the bar alone as its close to my office... but don't expect to be alone long if you're social.
Four Seasons Montreal is home to Marcus Restaurant + Terrace, the city's hottest destination to dine, drink & connect from visionary chef Marcus Samuelsson.
www.fourseasons.com
Fish Bone (old Montreal - reserve for 9-10pm)
Good food, great cocktails and gorgeous women. Try calling and reserving a spot at the far end of the bar... as it will provide the best view. Else you'll have your back to the entire room.
www.fishbonemtl.ca
Here's a list of a few known speakeasies
Down secret stairwells and behind hidden doors, this is the list of the city's best underground bar scene.
www.timeout.com
Want some live music in a more non-classy setting ? Give "Bistro à Jojo" a try its in the Latin Quarter... sometimes just a beer and very happy drunk people is a nice change of scenery
Bistro a Jojo | Bar et musique live chaque jour - Live music in Montreal 7/7 | OUVERT/OPEN 12pm-3am | MONTREAL (514) 843-5015
www.bistroajojo.com
As for touristy things... I'd be more the type to stop by the SQDC to buy weed oil and grab a Hop-On-Hop-Off tour bus to get a feeling of the city.
Discover Montreal in a unique way on a London-Style double-decker bus!
www.grayline.com
Note: sadly there isn't much SP activity late at night. Most agency girls will be done way before midnight. This has a been a very sad thing for me personally as I'm not one to book an appointment during the day and dislike pre-booking as I tend to hobby only when all else fails... I much prefer after a fun time out with a few drinks and some socializing. Call me old fashioned.