Reading all these posts makes me wonder: are you perhaps trying to do too much?
I think back to a comment by Anthony Bourdain about Paris: don’t try to do everything; just relax and enjoy the place.
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Your hotel is about half way between the Peel metro and the McGill metro. It’s about a 5 minute walk to either one. So if you would like to take the metro, walk over to either Peel or McGill, take the orange line to Lionel Groulx then the green line to either Champs de Mars or Place D’arms. Both metro stops are right in the heart of Old Montreal. It would take about 10 minutes to get there by metro or a lot longer by bus. (When I go to Montreal and am going somewhere on a metro line then I take the metro since it’s so fast.)
And just to note that while I agree Old Montreal is touristy there is a lot of history behind it. That’s where the settlers first landed and probably the oldest part of the island. Well worth the visit IMHO.
I agree with @BarneyGrubble you have a full itinerary. The nice thing about Montreal is that it is a walkable city. Lots to see and you are going at the nicest time of year. If I were going to Montreal I would pick a neighbourhood and take in the sights - a farmers market, maybe a museum, and enjoy a leisurely meal while I’m there but that’s just me 
Bourdain never had to worry about FOMO, he had people making all the necessary arguments and he had a huge budget. He also travelled 300 days of the year. Having said that, I don’t necessarily disagree with you.
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I like to have a lot on my travel wishlist. Some things will be closed and some things will have lineups. Good to have lots of ideas in case some don’t work out!
Well, yes. But much of what you see on my itinerary is negotiable/flexible - we don’t have to go to the various markets, museums, etc., nor even make every dinner reservation I have made. I like to have a basic plan and a handful of options in my back pocket to avoid wasting time on endless “what do you want to do/eat/see” back and forth with Mr. Bionda while we’re there. If I have plenty of ideas and a general idea of where things are/how long it takes to get from point A to point B, we get to see a lot more, avoid missing the things we REALLY want to do, and rarely get stuck eating bad food.
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I am not positive that’s the way his show worked.
I know that in Washington, DC he relied almost exclusively on the input of one food writer. And he went to very inexpensive places.
Yes, I figured that out from the map. As a New Yorker, I’m accustomed to adding 10 minutes for any transfer, so I assumed that trip would take closer to 15-20 minutes - Montreal’s metro must be much more compact and efficient than ours! Regardless, I can avoid that trip pretty much entirely by just staying in Old Montreal (given our restaurant itinerary and other plans), so I think that’s what we’re going to do.
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I am eagerly stalking this thread as I am planning at last minute trip to Montréal. Great info here.
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And he also went to some of the most expensive places, and some of the places he went to could not have been possible without a lot of planning and help from his “team”.
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It’s getting harder and harder to just meander the streets of many popular vacation destinations and just pop in for a bite without reservations. Some planning is very necessary these days.
I like Montreal, but I detest Vieux Montreal. It is one long street that is not particularly nice and the high points are not all that high or interesting, and it is a mass tourist glut. I find it repulsive.
I like Montreal in general… though you have to realize it is a weather-beaten city in which organized-crime-like control means streets and sidewalks and buildings are left in a constant state of needing repair with the work not actually getting done, despite signs of construction all over the place.
My favorite thing to do in Montreal is to climb the Grand Staircase of Mont Royal. You start from the intersection of Peel and Pine. It doesn’t take all that long to ascend, but it’s worth taking your time to stop and take photos. On top, there is a balcony with a great view. You can walk to the base from the Metro, but that itself is a big walk uphill, so you might want to consider Uber or public transportation.
The Botanic Gardens are immense, including a vast arboretum which will feature Canadian trees, so quite different form what you’ll se elsewhere. So that should be on your radar. The nearby Hochelaga neighborhood is a good place for food finds, and the Aube baker is exceptional.
And the Hasidic community of Mile End is where you will find St Viateur (go for the bagels that look a little bit burned and always go for ones coming right out of the coal oven.
Nearby, le Depanneur Cafe has live music all the time, mostly singer-songwriters performing half in French, half in English. Boulangerie Cheskie has a good scene and is a cornerstone of the Hasidic community, go for the baked goods on the counter right behind the salesperson.
If you walk any of the neighborhoods of Montreal like Mile End, you will see the residences have these tall, twisting metal exterior staircases. This is a very odd solution to the problem of getting to the second floor as these staircases are quite treacherous in the winter, but they do mark the unusual nature of Montreal.
And if you wan to eat like a native, then you should do carryout and eat it in a nearby park. Montreal parks are fitted with outdoor tables and chairs, and you can find people eating there at all hours.
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We’re back! Had a wonderful time and fantastic food thanks to all of you HOs. Our sightseeing itinerary ended up being completely different from what I outlined above, but it all worked out wonderfully. We arrived a bit later than we planned on Wednesday so didn’t have time for Bota Bota - opted for a stroll around Old Montreal and a later dinner at Le Serpent instead. A lovely meal but my least favorite of our three dinners due to VERY slow service, an uneven menu and prices that just felt a bit high for what was served.
Mr. Bionda started with the crudo trio, I opted for an appetizer special of zucchini blossoms stuffed with halibut “mousseline.” Both were weak - the dressings on two of three crudi were sort of sweet and bland, didn’t compliment the fish at all. My blossoms were fine, but what I was expecting to be a delicate and light filling actually had the texture of tuna salad - tasty in and of itself, but totally obliterated the squash blossoms both in texture and flavor.
Fortunately the pastas were better! We had the spaghetti with clams and the bucatini with pork ribs, nduja and soy. Perfectly cooked pasta, deliciously robust flavors, but both were a little skimpy on protein for the price we paid, particularly the bucatini - there was barely a shred of pork to be seen.
Dessert was a cherry and plum confection with an almond cookie. Very refreshing on a warm day.
We lucked into great weather the following day, so we finished our pedestrian tour of Old Montreal in the morning and then walked to the Golden Mile area and over to Concordia in the afternoon, punctuated by a surprisingly good lunch at the Time Out Market in the Underground City. Solid ramen, some interesting lobster dumplings with yuzu avocado aioli, and a nice steak frites for Mr. Bionda (from three different stalls). Forgot to take pics as we were famished from all the walking!
Took the metro back to Chinatown for a quick peek there and then back to the hotel to freshen up before dinner at Monarque. LOVED this place - big thanks to @THECHARLES for making sure it was on my radar. Excellent service, lively atmosphere, and a fantastic value - our meal here was $60 or so cheaper than Le Serpent and the food much more consistent. We started with toasty warm gougeres, followed by the bone marrow with escargot - this was outstanding, one of the best bone marrow preps I’ve ever had. Perfect balance of richness and acidity.
Then duck confit for him and the house-made sausage for me, both both excellent renditions of these classic dishes. Plus a side of sautéed local mushrooms that were absolutely divine.
Peach cobbler with corn ice cream for dessert - biscuit topping was a bit dense but the peaches and ice cream were lovely together.
More beautiful weather the next day, but Mr. Bionda decided he wasn’t up for Saute-Moutons due to a minor neck injury he sustained earlier this summer, so we hopped in the car to check out the cidreries and wineries west of town in St. Joseph-du-Lac. Beautiful area! We stumbled upon Fromagerie du Vieux Saint-Joseph and stopped in for a cheese tasting, then went on to La Bullerie for a bottle of their Aria (a crisp, dry white) and wood-fired pizza (only fair, their crust had a wonderful pillowy texture but BADLY needed salt, and the porchetta and smoked gouda topping, which sounded fantastic, was pretty blah in reality). We had to fight some traffic on the way back, but managed to stop in Notre-Dame-de-Grace to see my parents’ old digs, plus grab a beer at Messorem and do a little shopping at Marche Atwater, before heading back to the hotel to rest before dinner at Damas.
Damas is an absolute gem of a restaurant - gorgeous space, excellent service, beautiful food. We ended up ordering a la carte because we felt the tasting would be too much food and because there were several interesting dishes that were not included, specifically the fried kibbe and the friki, a short rib “main” dish I was unfamiliar with. We ordered both of those, plus the cold mezze tray and shish borek. Our waiter mentioned initially that 4-5 dishes from the a la carte menu was generally the right amount for two people, so we tried to order the rack of lamb as well, but he (thankfully) steered us away from ordering both that and the friki saying it would likely be too much food - and BOY was he right. We could have stopped before the friki and been perfectly satisfied.
Everything was delicious and beautifully presented. Loved their eggplant muttabal and muhammara. Hummus was good but not mind-blowing. Fried kibbe were probably the best I’ve had. Shish borek were DIVINE - tender pasta, and the combination of sauces really sang. There was a short wait for our friki so our waiter kindly comped us a couple of stuffed grape leaves - again, a fabulous rendition. The friki was also wonderful - a really interesting combination of flavors, temperatures and textures. We were far too full for dessert, but I did get a peek at our neighbors’ pistachio ice cream - looked amazing. Our bill here was almost exactly the same as at Le Serpent, and the whole experience much more enjoyable.
Our final day dawned rainy and grey - perfect football weather 
. We hopped in the car early and did a drive-by of St. Joseph’s Oratory and a quick stop at the top of Mt. Royal, then headed over to Mile End to grab a bagel at St. Viateur before brunch at La Binerie. I got a hot, fresh sesame bagel that was probably the blandest piece of bread I’ve ever eaten in my life. Do they not believe in putting salt in bagel/pizza dough in Montreal? Like, is that part of the Montreal style? Because it is dreadful. I abandoned the bagel after a couple of bites and saved plenty of room for poutine and tourtiere at La Binerie. Thanks again to @Phoenikia for this rec. Very fun, old-school place and I absolutely adored the tourtiere - it tasted exactly like the one my mom used to make (a recipe she picked up while living in Montreal, natch). And I think they use lard in their crust, which was a nice touch! The poutine was fine (that type of gravy isn’t my thing), but Mr. Bionda loved it.
We had just enough time before the game to grab some pastries at Kouign Amann for the road (kouign amann, croissant and apple turnover) - we ended up devouring the kouign amann while warm and ate the others in the car on the way home. LOVED the kouign amann - I had never had one that was a slice of a larger cake rather than an individual size and I think I prefer the slice format. Croissant was light and crisp but almost too buttery, if that is possible. Apple turnover was good but could have used a little demerara sugar on top for crunch and sweetness.
All in all, a great trip! Thanks everyone for your help - you HOs make all of my travel planning a joy!
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Damas looks great! Glad you ate well and had a good time 
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wonderful report @biondanonima
