If you’ve ever got a week to kill, consider making your way from Fort Lauderdale to Key West. Along the way you can stop at the different keys – each one with their own weird little personality – eating, drinking, snorkeling and beaching whenever and wherever you damn well please.
After a few days at Deer Key (known for their tiny adorable deer, are you fucking kidding me?!), we drove the beautiful overseas highway. And it really is just that – a four (sometimes two) lane highway that stretches out over the water, the tiny strip of concrete the only thing between you and the ocean, as you make the three hour trip to Key West. It’s a gorgeous way to get from one place to another if you’ve got extra time to kill and prefer the scenic route.
Once we landed in Key West, we decided to take a look around. Per usual, we hadn’t booked anywhere to stay for the night, and we hoped the travel gods would smile upon us. Key West is really, really expensive – especially lodging – although we heard that if you post up at a bar and ask around, people have extra rooms. And guess what? That’s exactly what happened.
After getting a drink at the famous Sloppy Joe’s (open since the 30’s, it was Ernest Hemingway who convinced the owner to change the name from Russell’s to Sloppy Joe’s NBD), we walked around town, eventually landing at Ruth’s bar, sitting next to a few guys who turned out to be boat captains. (One guy’s name was Jizz. Not making that up. He said his “Christian name was A.J, but everybody calls me Jizz.” Why? We’ll never know.)
We chatted them up and whaddya know, Jizz happened to have a sister who ran a bed and breakfast and would totally give a room for a hundred bucks a night (compared to the $300-$400 rooms we were finding online). Glory, glory hallelujah. The place also had a great pool and a daily free happy hour (IN THE POOL). Double hallelujah.
This boat captain also told us he could *easily* sneak us into Cuba for a few days, but after a few more shady details, we gave him a hard pass, but promised to meet up later for cocktails.
The next day we went on a snorkeling tour, which half of our party thought was great! The other half got sick in the water due to the rockiness of the waves and laid face down in the back of the boat for the rest of the trip, while I drank whiskey and chatted up the Asian tourists sitting next to us. Pro tip: if the snorkeling company offers to let you reschedule your cruise due to bad weather, just do it. It’s all fun and games til somebody starts barfing.
Key West is nuts for Ernest Hemingway. They love the dude. Like they want to take him behind the bleachers and get him pregnant kind of love. Fans of his fiction flock from all over the world to see the house where he wrote A Farewell to Arms, Death in the Afternoon and other classics.
The line is long and it costs a bit to get inside, but if you’re a bookworm you won’t want to miss it. Plus Hemingway’s life was so complicated and scandalous and incredible and old-timey in its drunkenness and machismo, you’ll need an entire afternoon to get through it all.
The guides do an amazing job of leading you around the property, telling stories, showing artifacts and pointing out the six-toed cats. The three hours we were there flew by.
After we finished our tour, we rode our bikes around the island, stopping at the Southern Most Point monument to get a picture. Unfortunately, 100 of our closest friends had also gotten the same idea, so we just took a picture of random people at it, and hopped back on the bikes.
Key West is not exactly known for it’s sprawling white sand beaches, but if you go out to the nature preserve, you can find a little stretch of sand to set up shop at.
After our night in Key West, we decided to head back up the coast, there were swamps to explore, Miami beaches to play on, and West Palm Beach cruises to sneak our own booze onto!
But before we went, we stopped and had some Key Lime pie. Just like Guinness is supposed to be better in Ireland or tacos are better in Mexico or Tequila is better in Mexico or margaritas are better in…you get the point, Key West is THE place to eat Key Lime pie. And I gotta tell you…it did not disappoint. They sell it everywhere, and for good reason too…the tartness of the lime mixes so well with the buttery crust and the whipped topping. it might just be my favorite location-related pie of all time. Top three at least.