Finding Out Just Who You Are

Babs and I just returned from a whirlwind 3 day reconnaissance mission to the Gulf Coast of Florida. We are thinking of buying a warm weather property in Florida and we have to check out the communities and the available properties and find out if we could actually live there or not. Since last Friday I have seen the Gulf Coast of Florida from Tampa Bay to Naples and back. Some of it is posh. Some of it is trashy. Some of it is a little funky. A lot of it is one long strip mall.

Funny how a little soul searching is involved in that. Babs and I have lived in Chicago for the better part of 25 years now and have ultimately landed in a high-rise downtown, overlooking Lake Michigan. This is part and parcel of who we are. So if we consider relocating to warmer climes when we retire, where will we feel comfortable? We're on a mission. True, we did take 2 years from 1993-1995 and lived on the island of Guam. We returned to Chicago, however. I remember a short-lived comedy many years ago about a guy who gives up his job and moves to Hawaii to open a surf shop, his life-long dream. Then, upon arriving and seeing his new home, he shakes his head and says, "I just didn't think it would be so much like rural Alabama." Guam was a lot like that.

Anyway, what we discovered while looking at Florida communities was that we have to come to terms with who we are and what tradeoffs we'll be making by leaving the life we know in Chicago. I believe it was CNN.com who had an article online a while back about what great deals could be had in the community of Port Charlotte, just across the bay from tonier Punta Gorda. We stopped in both places, and lo and behold, Port Charlotte, FL is a dump. No wonder there are cheap properties galore there. Who wants to relocate there? Went across the water to the supposedly tonier, pricier Punta Gorda. Yes it was nicer, but still, kind of small town and not the kind of culture we're really looking for.

Went down the coast past Fort Meyers to Naples. Yes it was much nicer, much larger, a great deal more to offer. Just a little problem there. Are there any people of color in the entire county who don't work serving the rich white Republicans who populate this place? Are there any funky, artsy sorts? Have to admit, I didn't see any. I guess I'm just not fond enough of boat shoes, Dockers, and pastel sweaters to fit in there. I probably have enough money to afford it, but I live in Chicago with African-Americans, Mexican-Americans, assorted artists, musicians, writers, gay and lesbian couples and we all celebrated big-time when Barack Obama was elected President. Naples? Nope.

I have to admit that we were getting a bit depressed over how the trip was turning out, but the next day we happened on a little town south of Sarasota, called Venice. It has promise. Then we wandered out to a little island called Siesta Key. Beach community. Condos, beach, bars, restaurants, and a lot of people under the age of 65. Did I mention that some of these Florida communities are filled with boring-ass retirees driving around in boring ass big old cars and living boring ass lives? God that's depressing. Yes I am 59 years old, but I just can't relate to those people. I can still run 10 miles. I still like the artsy life, and did I mention that I don't look good in Dockers and pastels?

Got up to Sarasota and downtown Sarasota is interesting. Went over the bridge out to Longboat Key. Upon first arrival on the island it looks a lot like Lincoln Road in South Beach. Not sure I'd like to live right there, but if you go up to the north end of the Key there are stretches of beach, nice condos, and lots of tennis courts and running and biking paths. Not bad.

All in all the Gulf Coast reconnaissance mission was a success. Babs and I have decided to rank our favorite places. As you may have guessed, Siesta Key, Venice, and the north end of Longboat Key rank #1, #2, and #3. At the end of next month we are taking a trip along the Atlantic side, from Miami Beach up to Fort Lauderdale and West Palm Beach-Boca Raton. The question becomes, "Can we afford it over there? Are there sufficient numbers of foreclosures to afford a good deal in one of those places? Will we fit in there?"

I guess one of the things we are coming to terms with is that we are not classic Middle America. We don't aspire to classic Middle America. We honestly like South Beach, and Key West. We like artsy. We like gay friendly. We like areas that attract free-thinkers and assorted liberals and loonies. There are perfectly good reasons why Babs left Iowa and I left Arkansas. There was a reason why we migrated to Chicago together. Seems Minneapolis just wasn't big enough to hold us.

The question becomes, "What place is funky enough to hold us now, yet not priced off the chart?" There is also a reason that Babs and I do not live in Manhattan. Simple cost-benefit analysis dictated a move to downtown Chicago instead. So yes, we may be artsy inclined, left-leaning, and reasonably well educated, but there is a practicality to us that Babs thinks of as quintessentially Midwestern in nature. We're not giving up what we have entirely just to live someplace ultimately warm and funky, only to have to live in poverty in a postage stamp sized abode.

There are no doubt those who wonder why we would leave our current place at all. We have floor to ceiling windows looking out over Lake Michigan, right in the middle of downtown, and mere blocks from the best of it all. We have the arts, the liberal community. The thing is, Chicago has been very good to us, and in the summer it is a place to be. It's just that the winter gets a little old after a while. When I'm 70 I'm not sure I want to be walking out the front door of this place in February while 20 mph winds whip off Lake Michigan and the temperature is 15 degrees. I think I'd like to live someplace where there is funkiness and art and liberal vibes and urbanity and where you can run on the beach year round. Oh and someplace where you don't have to drive everywhere you go so you can park in a parking lot the size of Wisconsin. Walking is good. Is that so friggin much to ask?