The Keys are truly a diamond in Florida’s vacation destinations. The state already has loads to offer but the Keys vary from being an adventure location to relaxation destination to the New Orleans of Florida. I feel like I was able to experience all these sides of this great area.
To start with, as a native Floridian I’ve actually never traveled to the Keys post 21 so this was a great opportunity for me to experience the crazy bars. The last time I was in the Keys I was 20 so it’s been a good seven years since however, not much has changed there. I actually consider that a great thing!
Now for the tale of the Key West Adventure!
I went with a mate of mine and we drove down from Ft. Myers. I realize they have the Key West Express but it was a bit too pricey and my car gets AMAZING gas mileage. Thank you Honda! The drive was relatively smooth with only about 30 minutes of rain in Miami. Honestly, it was great seeing how the landscape changed from Miami to being on the islands. So many mangroves!! After a long five hour drive we made it to our hotel. We stayed at a historic Key West Inn called Albury Court Hotel. It was a great location and about a five minute walking distance from Duval St. We didn’t plan this but our trip ended up being perfectly timed to the yearly Hemingway festival. Basically, that means there were a lot of older gentlemen with fantastic beards walking around. There were several events that went along with this like a look-a-like contest. The best event was the running of the bulls but we’ll get to that later! So the city was packed with people and of course it was very hot which is all you can expect from a Florida summer.
Our first stop on the drive was in Islamorada. We went to a place called the Holiday Isle Raw Bar and had our first pina coladas of the trip. This was a great stopping point mainly because the drive is so long and it’s nice to stretch your legs. Also, I hear they have the best pina coladas in Islamorada and it lived up to the hype. Not to mention the view of the water was amazing! After we reached our hotel it was well past dinner time but we decided to search out some fine oysters anyway. We went to Half Shell Raw Bar to get some seafood. The oysters Rockefeller was not what I was expecting (it had spinach in it) but the mussels and ceviche were totally on point. After that we wandered down to Duval to check out the scene. We ended up at Irish Kevin’s. I’m not going to lie the band was fantastic and very hilarious. My mate ended up being brought on stage and danced. They were great about catering to weddings/birthdays. It seems like a great place to start a night out of drinking. We ended up meeting some great people there as well.
The next day was our sunniest day and no rain was in the forecast. That made it our beach day!! We walked along most of Duval street to get to the Southernmost point and the Southernmost Point Beach. It’s a tiny beach but it has a bar for coverage from the sun and to get your drink on. It was so odd to see a line at the Southernmost Point buoy. I figured no one would be site-seeing in the middle of July in Florida but there was a good 30 minute wait that we did not partake in. Several hours on the beach later we were well ready for lunch. We went to a hole in the wall B.O.’s Fish Wagon which has the best tacos on the island. We liked it so much we ate there twice! It was delicious and cheap. My two favorite things! There were adorable little chicks with a few hens and roosters as well. The chicks were so cute and I even got to pet one! We went back to the hotel to clean up after the beach and get ready for a night out.
I wanted to do cliché Key West things so our first stop was Fat Tuesdays. If you like sugary sweet slushie drinks then this place is for you. I could only manage one though. It was super sweet overload!! After several drinks around town our search was on for dinner. We ended up at Turtle Kraals and I had the best potato skins of my life. They were incredibly tasty and with the addition of cilantro and cotija cheese I had to forcibly pace myself when I was eating then. Tried the ceviche here as well and it was oddly served with popcorn rather than chips. It was tasty regardless! After that we went to Irish Kevins again and a local bar Caroline’s. Then called it a night.
Our last full day was a bit rainy to start so we wandered slowly down to Duval. We made a point to make it to the Running of the Bulls/open market on Duval. The Running of the Bulls was pretty hilarious! Basically, a bunch of Hemingway lookalikes ride plastic bulls around Key West and on a float one guy holds a barrel of rum with a bunch of other lookalikes. It was definitely a site to see! There was plenty of time between the last lookalike contest and this event that we decided to go to Mallory square. Before that we hit up lunch at Pepe’s. This place is right across from B.O.’s. It’s a staple of the Keys and the food was amazing!! The photos inside show just how old and iconic this restaurant is. Of course we had to hit up Kino’s shoe shop. I of course bought a pair of Key West made sandals. Then we went to the shipwreck museum. Now, I am very biased. I am a maritime archaeologist and I’m not a big fan of treasure hunters and the like. I’m more into conservation, preservation, and the Indiana Jones ideology of “It belongs in a museum.” There were definitely a few things that made me question the intentions of the original ship wreckers and wrecking masters. It was very cool to learn the history though and the guy that lead us around was pretty funny. Honestly, the best part of this museum was the observation tower. It shows you a lot of the city and provides a wonderful view of the Keys.
After that we made our way back to the lookalike contest. It was fun to see all these people there for it including Paula Deen who I had no idea her husband was a lookalike. The drawback of this was the National Guard that was there. They were rooting for one of the Hemingway’s. They were rude and obnoxious. One of the lookalikes had bought me a few drinks earlier that day so I was of course rooting for him when they found out I wasn’t rooting for their Hemingway it was like all hell broke loose. It took the fun out of the spectacle which is sad because the whole event seemed so silly fun. It even raises money for a good cause. It definitely put a sour note on the event for me. After this event, I really wanted to see a Drag Show. So we ended up at Aqua and had a great time!! One of the Drag Queen’s was beyond fabulous! Actually, they were all absolutely fabulous.
Our last and final day was pretty relaxing despite the rain. We decided to go beer hopping while the rain was pouring on us. What else does a person do on a rainy Key West day other than drink? We started at Capt. Tony’s Saloon then wandered to Green Parrot Bar and then we ended up at Sloppy Joe’s. The staff there was incredibly nice even though the crowd had died down from the Hemingway event ending. We ended up talking to everyone at the bar and all of the bar staff including security. That’s the one thing I love about the Keys. At every bar we went to everyone was so willing to talk to strangers and to hear their stories. I am a total extrovert so I kind of live on these interactions with people. We spent the reminder of our night at Sloppy Joe’s and this is definitely a night I’ll remember hanging out with one of my best friends.
The next day was spent sadly driving in the sun. It was so sunny for our drive back we almost wanted to stay another day. Despite the trip being too short it was wonderful. My only qualm with this ENTIRE trip was that the point was to end up at the Dry Tortugas. We called three weeks in advance and they told us don’t worry about making reservations. We called two days before we wanted to go and they were full up. I was pretty pissed off! Either the communication within the company is bad or we were just blatantly lied too. Although, it does give me a reason to come and visit again.
I know we didn’t do all of the typical Key West sites, i.e. Hemingway House, Conch Train, snorkeling, etc. The fact is that my mate and I have both been to the Keys several times and we didn’t want to see things we’ve already done. I would suggest a sunset sailing cruise and definitely try snorkeling if the weather is good. Other than that, the Keys are a great traveling destination. If you’re ever going down that way, even if it’s to Miami, I would suggest going on the long drive down and checking out this wonderful seascape.