What do you think of when you hear the words Key West? Is it Ernest Hemingway? Cruise ships? Fat, drunken tourist making fools of themselves? Key lime pie? Stupid Jimmy Buffet songs? After finally visiting this Caribbean town stuck in America I can tell you that all of these things are there in spades. You can take a trolley tour and get shitfaced on Duval Street. Or you can seek the locals’ hangouts and avoid the famous sites. What I discovered about Key West is that you can be any kind of traveler there, and that is okay.

Going to Key West made me question myself. Can I enjoy a so called “tourist trap” of a place? Am I jaded? Have I followed the gospel of Anthony Bourdain too closely? Am I having an “authentic” experience and what the hell does that even mean anymore? Or more importantly, am I a big snob about where I travel? It turns out Key West is exactly what I needed before Michelle’s and my big adventure.

Family brought us to Key West. My mom has always wanted to visit there. She was boarding a Disney cruise ship in December (with my sister and her family) so we decided it was too good of an opportunity to pass up. Since we were missing Christmas with her we decided on an early present. We booked a small hotel room and bought her a plane ticket.

The first thing about Key West is that the drive down there is beyond brutal. From Miami, it is 2.5 hours of one lane, low speeds, an abundance of police, and a fuck ton of bad Midwest drivers. Although scenic, I was ready to drive the car straight into the Gulf of Mexico by the time we arrived.

My first recommendation to those visiting Key West is book a place near the sites. It is a small place and much easier to navigate if you can just walk, bike, scooter, or drunkenly stumble around. You will most likely run over an old blue haired lady if you try to drive around town, so don’t do it. Unless you visit in the off season you will probably pay a premium for that room, but it is worth every penny.

Key West is expensive if you are backpacking or on a budget. There are no $1.00 bowls of Pho in the street or $5 a night hostels. However, you can eat and drink without spending a small fortune. We booked a hotel with a pool so we could bring our own booze and not spend all of our money in bars. The pool also paid for itself with entertainment as we became acquainted with a 4 foot orange iguana as he tried to impress some lady iguanas in the area. He didn’t get lucky but he did climb and jump from tree to tree. There are Cuban sandwiches – $8 at Sandy’s for a huge sandwich and a side of crispy French fries. B.O.’s Fish Wagon and Garbo’s Grill served up amazing fish sandwiches and tacos for under $20 a person.

So there we are in Key West with my mom. There is no way we are not taking a trolley tour ($27, various companies) or visiting the Hemingway estate ($13, includes a guided tour every 30 min). Her friends who have all been there insist on it. I thought for sure these events would be anywhere from boring to making me want to pull my eyes out with seafood crackers. I was wrong. Turns out these tours can be quite humorous and full of stories of the eccentrics that lived in Key West over the years. I had no clue that Tennessee Williams was a resident along with Hemingway or that a former mayor had water skied to Cuba and back. Before Key West was a tourist trap, it was filled with crooks, swindlers, drunks, pirates, and all kinds of dirt bags. It was where people who wanted a different kind of
life went to have just that.

The history of Key West is where the magic is, not at the bottom of your 7^th beer at Sloppy Joes. So even if you backpacked SE Asia for 7 months or traveled the Congo in Africa, sometimes you just have to pay the 25 dollars and hop on a trolley. There is nothing wrong with it. It is freeing to do these things. I didn’t feel lame or like I was being a bad traveler. Sometimes, just being a tourist is the most authentic experience. Jimmy Buffet still sucks though.