The Key to Getting Key West

Key West Stroller

In order to fully appreciate Key West, one must walk down the street with an open container.

Before I had a drink whilst walking down the street, I felt morally superior to everyone around me: the youth-is-gorgeous (even if your tattoos aren't) 20-year-olds; the aren't-you-wasting-your time? 30-year olds; the OMG-get-a-life 40-year olds; the crazy locals of all ages who choose to spend all their time here.

The only people I didn't feel superior to were the occasional European families, the occasional, elegant, older couples, and the wholesome honeymooners who accidentally found themselves in the middle of one of the raunchiest parties in the United States.

Apparently, people who come to Key West buy shirts that say things like: 'I'm no gynocologyst, but I'm going to have a look.' Or 'F.U.C.K. Like You Mean It'. Or 'Key West: Where The Weirds Go Pro'.

I am so not one of those people. I don't even let my kids wear shirts that say anything (although I do let polo ponies and Quicksilver waves slide). God forbid I should ever convey a message through my clothing (or handbags, which is another story).

Key West is a lot of things. You can find charm, elegance and beauty, but aside from the local architecture, not easily. Ridiculous and hilarious trashiness, however, is everywhere. Monster motorbikes, comical golf cart conversions, Jimmy Buffet wannabes, sex shops, bong shops, tie-dye shirts, dreadlocks. Slightly less hilarious is the fact that many of the people who come here actually want this stuff.

But the minute I walked out onto Front Street with an open bottle of Prosecco and two cups, my judgement was suddenly gone. I didn't expect it to happen. Nor did I see it happening.

All of a sudden, I got it. I understood why people love Key West. You can do these things you can't do in your hometowns. You can push a stroller with one hand and drink a beer with the other. You can carry an open container of conch fritters in one hand and an airplane bottle of rum in the other. It's kind of fun to break the rules.

Especially when the rules are not against the rules.