Caroline St. Walkabout – Part 1

It seems the last few days I’ve been obsessing about Key West. OK… maybe I’m always obsessing about the place, but the last few days especially so. Anytime I’m overdue a trip to The Rock I begin obsessing.

To give me a little bit of a “fix,” I decided to write about Caroline Street. A few posts back, “Dear Ben,” I wrote to Ben Gentry about the Jimmy Buffett song, “Woman Going Crazy on Caroline Street.” The song is about Caroline Street in Key West. The lyrics tell the tale of the street back when fishin’ and shrimpin’ were king in Key West… back when it was rough and rowdy.

Click on the link to open another window to youtube. Let it play in the background as you read on. Woman Goin’ Crazy on Caroline Street.

Today Caroline street is different. So I thought I would take you on a “walkabout” down the street… if only in my mind. I’m including pics so you will get the feel.

Starting at the corner of Duval and Caroline there’s the Bull & Whistle. It’s one of my favorite bars to stop into and have a frozen concoction to help me hang on. “The Bull” is the downstairs area. Starting about noon and going well into the night they have some kind of live entertainment. If you sit by one of the open windows right on Duval, there’s plenty of entertainment out there doing the “Duval Crawl.”

Check out the roof top garden. It will be an eye opener

Check out the roof top garden. It will be an eye opener

The second floor is the Whistle. I can’t say much about it because I haven’t spent much time there. The Whistle does have a balcony all around so you can watch the Duval Crawl from there. I suspect it’s a great place to watch any of the hundreds of doo-dah parades down Duval.

The third floor, actually the roof of the Bull & Whistle, is… well… I’ll leave that for you to discover for yourself. Go there on a cool afternoon (in Key West that means the low 80s) or one weekend in the evening after the sun sets. I promise you it will be an eye-opener for you.

We start our walkabout heading toward the old seaport… away from Mallory Square and the Cruise port. By the time you are one short block away from Duval, all the craziness is left behind. Caroline becomes a sedate, almost stately neighborhood.

Tall mature trees and palms line both sides of the road and almost form a canopy covering the street in some places. The houses are mostly two-story with a mix of colors and surrounded by white picket fences. Most have a wide veranda around the bottom floor and a balcony around the top floor.

Many of the houses have been divided into small apartments. Most of those are little more than the size an efficiency in any other town… around 300 square feet. Each one costing way more a month than the original cost to build the entire house. Such is the cost of living there.

Sedate and stately just one block from Duval

Sedate and stately just one block from Duval

If these houses could tell stories, I wonder what they would say.

If these houses could tell stories, I wonder what they would say.

Walk a little more down toward the seaport and a bit after you pass Elisabeth Street, you will come to my favorite little coffee house in all of Cayo Hueso… The Coffee Plantation at 713 Caroline St.

The Coffee Plantation is half coffee house, half art store. I found the place because an artist I know once lived near there. I always stopped in hoping to see some of the artists work or to maybe run into the artist. But that was not to be… the artist had moved before I found the Coffee Plantation.

Have a "cupa" and enjoy the "mullet wrap."

Have a “cupa” and enjoy the “mullet wrap.”

Just the same, I still go to the Coffee Plantation every time I’m in Key West. Besides good coffee, you can have a seat in one of the couches inside or around the outside porch. Inside you’ll see some magnificent local art. I always want to take some home… until I see the prices.

So I just sit there and sip my coffee and maybe read the local newspaper… the “Key West Citizen.” Some call that paper the “mullet wrap.” Like most newspapers, it has fallen on hard times lately, but it’s always an interesting read. While sitting there, inside or outside, it’s more than likely that you will strike up a conversation with another of the patrons. It seems like most people are friendly there.

Next up… Caroline Street, part 2



Leave a Reply