We started looking for our vacation/retirement land several years ago. We've lived in many sections of the US (and even outside of it for a memorable 10 months) so we had a feel for the type of area in which we wanted to live. We love the Northeast - usable seasons, good people, and lots of cultural activities. So we concentrated our efforts there.
We took vacations in Maine, Vermont, New Hampshire, Massachusetts, and New York to see areas we liked and to solidify our wants and desires. Eventually some basic requirements ruled out several otherwise desirable locales. The property had to be: within an hour of a major airport, within our budget, and reasonably close to basic amenities (grocery, Target, Home Depot, good bookstore, the usual). Gradually we realized that we wanted a place closer to work so that we could enjoy it on the weekends. Too many people we know have camps multiple hours away and that seems to create more trouble than relaxation. So that effectively ruled out Maine and New Hampshire.
We were very lucky in that my father was also looking for retirement property; that allowed us to add another set of eyes to the search. It also meant we could look at larger parcels. We had found that small (10 acres or less) parcels came with high per acre costs, but large parcels were much more reasonable on a per acre basis. The downside was that you ended up with a lot of money tied up in land - not something that was in our budget. Having Dad look with us opened the possibility for subdividing a larger parcel - getting the best of both worlds. Then my brother decided he wanted in too. Woo-hoo! Now we were really on our way to finding a suitable parcel.
And find it we did. Mid-November of 2007 we were driving around looking at some land-for-sale ads that we had found on Craigslist. Although none of those appealed to us, we did like the general area so we decided to drive around and look for For Sale signs. Amazing how many there were out there. We had driven down a dirt road with no sign of civilization and Chris realized he needed to heed the call of nature. We pulled over and got out of the truck. The breeze was whispering through the last of fall's leaves on the Beech trees and I knew. This was where we were going to buy. Thank God Chris had to pee.