Do you think my Japanese wife will like my solution to our Toronto housing? Buy-in for about $100K for a luxurious 42' sailboat used in good condition, $600/month dockage fees, and it travels. Sweet! More comfortable and larger than a Japanese home, or a Toronto condo. Where's the down side?
I rather doubt my plans will go so smoothly for sailing a 27' boat, but I'd like to introduce my kids to isolated scenery in Canada before I'm too old, and they get busy as teens. I'm fortunate to be a teacher having the two best months of the year off to sail. The boomer teachers bought cottages, but they're all priced out now, and why would I want to spend my vacations fixing a second building (as opposed to a boat...).
2019, 49 years old, take a proper sailing course.
Buy a shared 27' boat.
2020, 50, children 10 and 7: Georgian Bay and North Channel
2021, 51, children 11 and 8: Georgian Bay and Lake Huron
2022, 52, children 12 and 9: Superior
Buy (or buy out) own boat, or get my co-owner to join the longer trip, possibly upgrading to a 32' boat, as much for room as for safety.
2023, 53, children 13 and 10: Huron, Eerie, Ontario, St. Lawrence River, to Saguenay
2024, 54, children 14 and 11: Gulf of St. Lawrence
2025, 55, children 15 and 12: Gulf of St. Lawrence
2026, 56, children 16 and 13: Newfoundland and Labrador
Much bigger plans would have to wait for retirement, which could have been sixty if I'd planned better, or had one fewer children to educate: more likely sixty-five; however, I can work a reduced year from sixty, so a four month summer is possible.
I'd love to take a boat further up the Atlantic to Baffin and Greenland, but even in summer that's an undertaking, even if I'd have the experience above. Getting my Japanese wife to join and miss all of a summer's weather? Be more likely to keep the marriage with a Vancouver to Juneau, Whittier or Anchorage passage. Probably have to stow the boat and return the next year the same way. I wonder about sailing Alaska to Hawaii...