I kept referring to (and still refer to) Key West as “Cuba” every time I mention it. I’ve never been to Cuba, so I’m not sure how far away from the truth I am when comparing the two, but the Cuba of my imagination is similar to Key West for one reason or another. I do, however, have some minor experience with the Caribbean which Key West strongly resembles, appropriately, so maybe it balances out. Key West is a strange mix of tourism and not, the island broken into what feels like districts catering to either locals or visitors. This is most apparent as you first cross over the bridge and see the familiar hotels, chain restaurants, chain stores and markets. Nearer the opposite side of Key West where the United State’s Southern Most Point marker can be found seems to be the other large tourist chunk, this area defined more by the coast and series of road arteries with higher priced boutiques and bars.
We didn’t do much I’d consider touristy, though it wasn’t completely for lack of trying. The Ernest Hemingway Home was a little expensive for our taste ($13), so my wife took a picture at the entrance being careful to block out the wall and ticket booth to make it look more like we went. I’ve only recently gotten okay with Hemingway again so it would have been neat to make a visit as a part of that reconnect, but I figured I could just as easily look up pictures online and spend the saved money seeking the best Cuban coffee in Key West. Place called 5 Brothers Grocery and Sandwich Shop won out. We checked out the southern most point. Saw a number of roosters. Key West has roosters the way large cities have pigeons. At the Six-Toed Cat – right by The Hemingway Home and a spot where you can get some great french toast – the birds just walk around beneath the outside tables which made for a strange (and strangely welcome) experience. Lunch was eaten at a place a little off the beaten called Firefly which my wife said seemed like “us”, a result of the music, the food, and the overall atmosphere. Casual would be a good way of describing it, though casual steeped in late 90s, early 2000s rock. Though the food didn’t knock our socks off – BLTs and Fish Tacos – it was far from bad with a price more tourist than local friendly. Recommended still.
Overall Key West wasn’t the most amazing place I’ve been to, and if I had to do it again, I’d personally say fly in rather than drive in. The Time Spent to Interesting ratio isn’t skewed favorably enough to warrant the extra hours. I think Key West would be an excellent spot to go to if you’re planning to sit for a week where you can hang out on the beach or the pool in between visits to the hotel or trips “downtown”. Though I’m sure it’s an obvious conclusion, Key West doesn’t feel right when experienced quickly as there’s little to hold the attention for too long. Dolling out time is the better way I’ll bet, and as that’s something we didn’t do.