Dear Montreal,
My wife and I are now in a position where we can travel. She has never been out of the country and my experience is limited to some Caribbean travel.
We have settled on Montreal in late September early August as our first international trip and have an open itinerary as to what we will do there.

We would like advice on where to stay, things to do, and places to eat.

We have never used air bnb but the places we have seen our nice and the prices good.
Art, history, animals, food is what we are looking for!

Please give us some cannot miss attractions and restaraunts as well as other ideas and advice.
Some questions
Do people tip in Montreal?
Any concerns we may have for safety or security?
Anything we may need to know?

Where shall I begin?

I’m in Montreal once a month and love it. I use Airbnb exclusively now and only stay in a Hotel when I’m in Maine/NB or have to go for an overnighter.  Since winter sucks ass in Canada, there’s tons of stuff going on in summer.  For a vacation, I’d recommend not renting a car as gas is 3x what it is in the US, and parking absolutely sucks in Montreal. Use Uber, taxis, Metro or walk.  One of the Taxi companies has Tesla’s which is different and pretty cool. I really enjoy Old Montreal/Old Port which is 300+ years old and on the the river. Lots of shops, food, things to do. If you’re into roller coasters, La Ronde is a Six Flags and is a good day trip alone. Olympic Stadium, Botanical Gardens, Gold Mile, China Town are good attractions as is all the church’s/cathedrals. If you’re into hockey look at taking a tour at the Belle Centre, but make sure you do the English one unless you’re fluent in Québécois. Restaurants and bars are everywhere and most have terraces on the street/side walk. If it’s nice outside I recommend sitting outside. There is litteraly thousands of restaurants in on the island and I could recommend a hundred. It’s all in what type of food you want to eat and the price youre willing to pay. Pack a couple small compact pocket type umbrellas just in case. Carrying a backpack is a good idea for water, umbrellas, and when you buy tourist stuff. Depending on where you go, you may see/use a unisex washroom (bathroom). I’ve seen women in the homme washroom several time during hockey games. It’s not a big deal, just different.  Montreal is a pretty safe town for the size. DO NOT bring a gun, ammo, spring assisted knife, pepper spray etc with you.  Canadian laws are not like US laws. If you injure someone in self defense, you’re screwed. It’s almost better to just walk away. Check with your bank and cellular provider before going. You’re in a different country and they will shut off you debt card, cc and bend you over on data usage. Check with your bank about getting some Canadian cash too. You can do the currency exchange at the airport but they’re not cheap. It’s damn near a one for one. If you can pick up some French between now and then it will help out. Everyone speaks English, but it’s law to start a conversation in French. The airport has streamlined customs and is nice now. You’ll arrive through C80 something and walk up to the third floor then walk to customs down the long ass hallway. You will be treated in French just respond in English that you don’t speak French. Go to the kiosk and enter your info/scan your passports get your customs printout then proceed to the CBSA Officer. They’ll ask you the standard questions where do you live, where are you going, why are you here, when are you getting the hell out of my country. Get your bags then go to the second check and turn in your customs form and you’re home free. Go across the street for a rental car or upstairs to get a cab or Uber. Sorry if I’m all over the place, but I’m tired, multitasking and drinking biere.
Where in Kentucky are you?  I live 4 miles from Guthrie. I’m flying back up on the 22nd and can look for some tourist flyers for you. Feel free to ask any questions and I’ll try and answer them. If you’re there when I’m there, I’ll buy the first round.
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Oh!  Order some Poutine. And did I mention parking is awesome.

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TnMike, thanks for the info! Wife and I live in Louisville.

Not a problem.
You will have a good time. Just don’t plan on being in a hurry, everything is casual speed.
Not sure about your flight plans but I always fly Delta and there’s only 3 connections into YUL from our area. Detroit, LaGuardia, and ATL. I prefer Motown as its normally a faster route and not a bad airport. IMO, 1st class is not worth the money because the flight is pretty short and is always on a shitty CRJ 700 or 900. Delta comfort or the exit row is where I’m happy since I have long legs.
You’re a good 3hrs from me. If I find some tourist books, I’ll mail them to you or if I can make it to the Creek in April we may be able to link up.

Hahaha. Ouais, and not an American from like up state NY or VT either. Don’t be so hard on yourself. Québec isn’t in Canada, it’s an independent country

Haha. It’ll never happen.

Make sure you don't bring any firearms. Auto knives are banned. I would bring a small folding knife, assist knives are ok as long as you can't flick them open (tighten the pivot screw). Montreal is safe.

They speak english, so don't worry about learning french.

I agree with Montreal being safe. I’ve been to a few shady areas and felt okay.  I feel safer on the est side of Montreal at night than Times Square during the day.  A vast majority of people speak English in Montreal.  You tend to get a little better service if you try and speak Francais, IMO.  I had a chick at a Subway in Laval try to play the “I don’t speak English” crap with me. Once I started with French in the thickest Southern US accent I could do, she quickly learned English.  Now, if you get to the rural areas of QC, they tend to be a little bit more legit with not speaking English, fluently that is.