Lately I've been preoccupied with retirement, in fact I've been preoccupied with retirement since I was 14. This is a bit disconcerting considering I'm not even 30, nor do I currently have a career, yet am daydreaming about never having to work again. The original daydream I had when I was 14, was retiring to a ranch in the mountains outside of Denver, Colorado. I figured land is cheap, yet still close enough to a reasonably sized city to enjoy professional sports teams, major airports, and city life in general. When I spent my year in SLO, I changed the vision to retiring to a winery outside of Arroyo Grande. It has better weather, relatively few people, yet still a downtown area to enjoy. It also has a beach nearby, and my family and friends are a half days drive away. Then I visited Lake Tahoe, my vision changed once more. A place up in the mountains, with some land nearby, and escape from city life, seems grand. But, recently I've been thinking it is too far from a major city. If I have nothing to do, I think I would get bored, and should live some place with options. Particularly, since I'd be old, and not able to enjoy the outdoors with my current stamina, not to mention dealing with the winter in an advanced state.
Lately, I've been thinking the bay area, but as I'm sure you've noted, I want to retire someplace outside of the city, where I can pick up a large chunk of land. Hence, I've been thinking either the Santa Cruz mountains or between Novato and Point Reyes. I don't want to go too far inland due to the heat, nor do I want to go coastal due to the cold (I think the wind could literally drive me insane). Both areas would be in the in-between zone hopefully keeping temperatures at a reasonable level. The Santa Cruz mountains, is wooded, has nicer beaches nearby, and closer to southern california (where I picture my brothers ending up) but is also closer to Palo Alto, and far from the city. Novato/Pt. Reyes is slightly closer to both Berkeley and SF, closer to Tahoe, traffic is better, but is also far more rural than city. If I could buy a large chunk of land in Mount Diablo state park, Tilden, Briones, or any other park between the bay and Livermore, that would be perfect, but that isn't going to happen. I just want to be able to wake up, wander around, and not have people breathing down my neck all the time.
And of course I'm going to have the money to afford these properties. Of course, space in both these places will still be bountiful. Of course, neither will change over the course of the next 30-40 years.
Anyways, do you have retirement plans? If you could own a large property, where would it be.... mountains, carribbean, desert, coast?