Ferry bookings open on Monday 29th May 2017 for TT 2018. Not sure if it's 8:30 or 9:00 am (UK time - BST). I've always found that the website crashes and have spent ages on the phone constantly hanging up and re-dialling until I get through. Might prove costly from Canada! Perhaps your best bet will be flying as you'll have to fly the majority of the distance anyway. Prices of flights or ferry during TT rise quite dramatically. Might be worth looking sooner rather than later to make sure you get what you want.

If you can do the full fortnight that's great. Weather permitting practice runs on the opening Saturday then every night from Monday - Friday. First race day is Saturday after practice and then alternate days (Mon, Wed, Fri). We tend to do practice week and the first few day or two of races as if the weather is wet you have more days of action, but race week is where it's at! Races do get postponed to later days in really wet years so you might see racing every day in race week (or none at all if you book practice week to Saturday and Saturday racing is postponed).

The Island is pretty small so it doesn't really matter where you stay, you can get to the circuit easily enough. There are all manner of options from camping to large houses to fit your group size and budget. Many are booked year on year by the same people so you need to get on this early to get exactly what you want. A lot of homestays and house rentals like a minimum of 7 days, but the distance you're travelling to get there I don't suppose that's a problem.

Unless you plan shipping it home you might find bike rental easier than buying. My guess is that you'll need to get onto this pretty quickly (supply and demand) especially with a big group. I have no experience of this though so others may guide you better.

When you've been once you will want to come again and again, and will quickly learn what works best for you.