We're considering either Toronto or Vancouver for next year! This was our fourth time back to Montreal and, although we love the city, we don't want to get stuck in a rut. We bought an Opus card this time and used the Metro quite a bit. A 3-day Metro card was less expensive than ONE Uber ride! The price of Uber was INSANE this year. It cost us nearly 50$ CAD to get to the airport.
Your trip sounds incredible. I can't wait to hear about it when it takes place. That will be well worth the cost and the planning. I highly recommend Airbnb Experiences. I've taken quite a few and they're always stellar. This is how we found the Ax Throwing and the Painting Class.
I like Airbnb as well. But I prefer it's older cousin. VRBO.com. I've been using VRBO since around 2005 and have never had a bad experience. For larger groups, you can get a castle and/or a mansion in the Hollywood hills. All the way down to a long boat in the canals of Amsterdam.
We've used VRBO as well and like them too! Do they offer "experiences" as well as accommodations?
As far as I know, VRBO only offers the accommodation. We'd need to add the experience ourselves.