We have a lot of Canadian friends that have invested into properties on the various Hawaii islands, especially Maui, where they spend up to 5 or 6 months of the year living. Typically they've bought in their early to mid fifties and some are now well in their late 60's early 70's still wintering and sometimes splitting winter and summer trips.
Others prefer to rent and typically use the vrbo.com website to find a suitable condo to rent for a month to several at a time, returning year after year. Most cite that they love the more temperate climate.
Hawaii never appealed at all to us, until our youngest daughter asked us to postpone our silver wedding anniversary trip planned since the day we wed to go to Australia RVing for 3 months. Her deal was if we did Hawaii that year so she could come (LOL), then she'd be able to come to Australia at a later date after finishing school. ahhh hmmm! Who's anniversary is it????
Seriously, we never would have believed how much we totally loved Maui and all the water sports and fun we had back in the mid 2000's, especially with it being such a small island. Look forward to exploring more in future years. Just so many places to go, people to see and things to do = ain't life grand
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It Takes No More Effort To Aim High Than To Aim Low - Reach For The Stars