How much are we talking here? I assume no more than the biggest lotto payouts? Let's say... $400 million? Spain's got the biggest, but it's split between so many tickets it's not the same.
Well, a solid $15 million would go towards building a dream home somewhere within Toronto. I won't pretend to know enough about architecture to do it myself, but I would share my tastes and ideas with a hired pro to see what's possible. I'd probably dump that much back into the real estate market here and use the rental money as income, since there's no signs of it slowing down any time soon.
I'd pick up a 2013 Vanquish ASAP. Not here of course; I'd submit my personal build and then fly over to Gaydon to get acquainted. Before leaving, a few million would go to family members to pay off houses or debts or anything of that sort, with some spending money on top. But I'd be quite clear that they wouldn't be coming with me across the pond, and likely wouldn't be hearing from me for at least a few months

. I'd go visit Evo's offices and see if they wouldn't mind taking on another Simon George-like contributor, and probably look at buying some sort of living space... somewhere in England. Not entirely sure where.
The Vanq would start a trip across Europe, taking in far too many locations to name. It might need a break by the time I get to Italy, which is perfect, since my Aventador would hopefully be ready by then (let's pretend I can get a bump up the wait list). Only then would I have the right chariot to visit Maranello

. I think I'd hunt for something a bit more maneuverable for any further driving though; probably a Z4 M Coupe, one that I could eventually have shipped back to Canada easily enough, with an M3's V8 awaiting placement in that engine bay.
Once Europe is dealt with, off to India for the Taj Mahal, followed by China for the Great Wall and a few other sights. Then, off to Japan for a good month or so, and the likely purchase of Living Space #3. I'd try to source a few mint mid-90's JDM-only cars, since Canada allows anything up to '98 these days.
After that, down to Australia for another few weeks, and a week or two in New Zealand, before taking the big trek to Hawaii. I probably wouldn't stay more than a week, and fly over to California for another solid month's worth of fun. Living Space #4 purchased, I'd also buy a convertible Mustang GT and make friends with the PCH, and Mulholland Drive. Oh, and a Boss 302 as well, because why the hell not? I'd then draw a wild S across North America, slowly working my way East, then North, with the goal of NYC before heading West again (after, needless to say, a
lot of time there). Say hello to the home of Frasier Crane, visit Blackbird, and pop back into the homeland via British Columbia. Just because it'd be an epic drive, I'd avoid flying over the prairies, and make it back home to a hopefully-finished new house. I'd throw one hell of a party with my friends, and look into getting investors for building a quality track just outside...
Townsend, my hometown. Lord knows nothing else goes on out there, and it's actually only a 90min drive from Toronto.
I'd erect a garage there to house what would quickly become a sizeable collection; I'd be on the hunt for any McLaren F1's that pop up for sale, with the explicit desire of actually driving the thing. The garage would double as a museum, and a driving experience/school would be included with the track construction. Once the track was finished, it would play host to not just sports car racing, but... the first GTPlanet World Meet. A special week-long event celebrating all things automotive and sim-racing. I'd cover the expenses for certain must-have appearances, and maybe we could even snag Kaz himself to host the opening night festivities?
