When I win the lottery
There are a bunch of people whose lives I think I can improve somewhat. And I will do that first.
I don’t really have a bucket list, I have done and seen more than I could have ever dreamed. But if I had resources, there are things.
I would watch the Monaco Grand prix, from the setting of the first jersey barrier till the last yacht leaves the harbor. I might do Silverstone too.
I would watch it rain on every continent where it does rain, watch thunderstorms gather and loose their power everywhere I could.
I would tour Chernobyl to the extend that it could be toured.
I would spend the rest of my summer vacations in Rudyard Kiplings home.
I would pay Jackie Stewart (Or whatever charity he desired) to give me a weeks driving lessons.
I would get Maserati to let me build my own car in their factory, working along their craftsmen.
All pipe dreams, of course, but fun pipe dreams to have, fun daydreams to enjoy on the way to work, or in bed on chilly winter mornings.

Regarding the lottery my father would say, “For a buck you can dream.”
I spent a day at Kipling’s house in East Sussex two summers ago. It was warm and sunny and the sound of bees and birdsong drifeed in the window from the garden as a local college docent spoke about Flanders, and Jack Kipling, and how that ruined Kipling and how he persevered. It was heart rending but probably the best thing I ever did on vacation.
Those are some good ones. I especially like the ideas of watching it rain and building a car. Why Maserati, specifically?
Maserati, because they are so breathtakingly beautiful, and you need to know how to fix them. Also, if i build it, there will be no shortcuts taken.
And Shermlock: Sometimes those dollar dreams have given me a days amusing meditation. Your father was a wise man.
No personal experiences with any cars with a trident badge but I can’t fault your tastes. The ones I’ve been in restraining order distance off looked like somebody carved a car out of a block of expensive sex.
Personally my lotto winnings would go to learning. Buy a small RV, drive up North a bit until I find someone making birch bark canoes the traditional way and beg them to teach me. Find a good blacksmith somewhere and learn how to convince metal to go along with my ideas for a bit. Spend a while working under a master cooper.
Who knows, I might even manage to make something along the way.
BGM
Nothing like a play on the lottery. What ifs are fun to play.
I would move to Texas…having lived there, they struck me at that time as being some of the most generous/friendly folks to have had as neighbors. And there are some dear friends there I would love to be able to see again.
Set up trust funds for various members of my clan (aprox 16 at last count).
Give to various causes/charities…and the 10% to God.
Finally, take Deb around the country … to all the places I have been stationed (and then some). Followed by criss-crossing the globe, with the same idea in mind. I imagine we would make a rather long stop in Greece (at least the islands) or Singapore, as she is fond of both. Me, I would like to see Prague in Spring…perhaps looking up relatives while there.
Sounds like a great deal for just a dollar!!
Buy a place in the southern part of Central Florida & never be cold again. A place with a huge garage(s?) to hold all the bikes I’d be collecting (hell, I have 5 now on my income; that’s why I bought my parents’ old house–it has 2 garages.), & gun safes for all the weaponry. Gotta have enough land for at least a 200-meter range, too.
A man can dream.