We started by shorter trips. Weekend trips to places that had
campsites already. Tobermory is a great trip, btw, if you can make it
that North. We didn't do any cold weather stuff though.

I would say work yourself up further and further. Trial and error is
important. Know (test) your equipment before you find yourslef
rebuilding stoves 2 days into the field (my buddy didn't test his so I
was rebuilding it). Don't take stuff you don't need, know what you
need by doing eventually longer treks. Kayaks can pack a lot of stuff,
but you stilll have to be smart. Dry bags are your best friend. They
are inexpensive, get many.

Alex, would love to see your winter camping photos. Post on Flickr.

Cheers