Road Trip Through the Florida Keys

I always feel a bit foolish admitting this, but of all the places I’ve been, Key West is my favorite. Yep, in all the world, my favorite place is a 4×2 mile island that doesn’t have good beaches and is known for bar crawls. Perhaps the reason I love this island is because, aside from college, this was the first place I ended up when I left home for the first time; I showed up bright eyed and bushy tailed at the ripe old age of 18 for a 3 month internship, and I did a lot of growing up there. Despite how young I was, I learned a lot about life – mostly that it should be fun and not taken too seriously (something that, outside of Key West, is easy for me to forget). All of that to say that the end of the day, I’m not entirely sure why Key West is my place, but it doesn’t really matter. It is more than coral-ridden beaches and bar crawls to me. Key West is magic; my troubles and worries disappear (okay, maybe not entirely, but they seem smaller) and I turn into a more laid back version of myself every time I’m there.

I recently felt like I needed a bit of a break so my husband and I decided to take a day off of work for a 3-day weekend. We discussed many destinations but ultimately decided to explore the upper-mid Keys. While I’ve driven the length of the Keys twice in my life and my husband has been to Key Largo once (for work, not for exploring, unfortunately for him), neither of us has spent much time exploring the islands outside of Key West and we decided it was time. 

My husband is very much a free spirit while I’m more of a free spirit wannabe. My fly-by-the-sea-of-his-pants husband requested that on this trip, we not do any prior research but rather show up and go where we felt called. Aside from checking a hotel search engine every few weeks to make sure there would be availability somewhere and a small amount of prior knowledge on the area, we didn’t do any planning. We just showed up and wandered. This approach couldn’t have worked any better for us. I’m convinced the trip wouldn’t have been as fun if we’d planned it, but it’s worth noting that it likely worked so well because we were traveling there during the off season. The Keys are a popular destination, so most of the time, hotels can fill up quickly.

The second we crossed into into the Keys, I immediately started asking my husband, “Don’t you just LOVE it?!?” and “Isn’t this just the best thing EVER?!?!” over and over again. Bless his patient heart. But love it, he did. The second we hit the bridge and saw the turquoise water, it was all over his face. Whatever it is about Key West (and clearly, all of the Keys) that captivates me had also captivated my husband, almost instantaneously. We rolled the windows down, drove slow (but not too slow because we don’t want to be those people), and took it all in. You could not wipe the smile off of our faces. 

There are a lot of itineraries out there to help you navigate the Keys, but this isn’t one of them because we didn’t follow any sort of plan. I know we’ll be back as many more times as we possibly can, so perhaps in the future I’ll put together a more formal must-see list. For this trip, we just drove to where we felt called. We drove around adorable little towns, looked at big beautiful houses, pulled over to catch the views at public parks, and shopped at locally owned companies. We just enjoyed the present moment and each other’s company. That’s it. 

Right when we were ready for a little break from the car, we found the Islamorada Brewing Company. Even if we hadn’t been ready for a break from driving, this would have been an obvious stop. They have the most beautiful outdoor area full of games (we opted for ladder ball) and it was a beautiful day to be outside (it was cloudy the entire time we in the Keys which seemed to really helped the temperatures). I could have stayed here all day and honestly really wanted to, but we knew that there was more to explore.  We didn’t make it much farther down the road, though, because we quickly came upon the Keys Brewing Company, where they had the friendliest employees working that I’ve ever met. And of all the breweries I’ve been, I think that this place wins best decor – it was so vibrant and fun! Both breweries were incredible and both had great beer.

Our next stop was some good food! Our only requirement for lunch was a waterfront location and there is no shortage of such options all throughout the Keys. You don’ t even have to google where to go because billboards will give you plenty of options; choosing from a billboard was kind of a fun way to choose lunch and fit perfectly with our “theme” of not planning ahead. We ended up at the Island Fish Co., where we had an amazing lunch with beautiful views of the water and some of the locals (if fish are considered locals). It was there that we browsed nearby hotels as we were slightly worried that if we didn’t book a place nearby, we’d end up driving all the way to Key West. Which, of course, wouldn’t be a bad thing, but since we know Key West like the back of our hands, we preferred to stay in the mid Keys.

From Island Fish Co., we headed straight to the hotel where I immediately jumped on a paddle board (included in the daily service fee) for the first time. I caught on relatively quickly and now paddle boarding is my new favorite thing. Like, ever. It has been such a long time since I’ve tried something new and it was a rush of pride, joy, and excitement! We spent the evening biking around the island before the sun went down and landed at the most beautiful park recommended by the front desk staff. We were blown away by this little Key that we had never even heard of. 

It’s safe to say that it isn’t just Key West that has my heart anymore. It’s all of them as a whole. I love them, I love them, I love them. I cannot picture a scenario that does not end with settling down there forever.

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