If you’re anything like me then you probably spend too much time planning out a perfect outcome in your head to most things in life. Whether it’s how that new dress will look when you wear it out for the first time, how delicious the food at that new place you’ve been wanting to try out for so long will taste like or in this case, how magical every little detail of that last summer getaway will pan out. We planned, we missed places and things we shouldn’t have (if one can only eat ten pieces of key lime pie a day), were disappointed about the things we thought we’d love but in the end, were enchanted with this uniquely vibrant part of Florida.
South Beach, Miami ✧ Ocean Drive
It was early summer and we decided to book a 5-day trip to Miami to celebrate my 32nd journey around the sun to bask in the salty waters of the Atlantic Ocean while enjoying the abundant state of sunshine. During those 5 days, we also decided to rent a little convertible and knock off one of our travel bucket list items - the all-iconic American road trip from Miami to Key West along the Overseas Highway. Our other bucket list road trips include Route 66 and the Pacific Coast Highway.
I was already starting to dream up the perfect image in my head of us two in the bright - colored little convertible, wind-in-the-hair, epic playlist adventure through the Florida Keys surrounded by the open blue water.
As soon as we got off the plane, the first language we heard in the terminal was Spanish and just like that, we knew we had picked the most perfect place to visit. We arrived at Sixt car rental shelter super excited to pick up our little colorful VW bug as seen in the online photo, only to find out they no longer had any available. Slightly disappointed, we picked a white mini cooper, smashed our suitcase in the minmature trunk (thankfully, we decided to leave the second carry on at home, otherwise it would have stayed at the aiport) turned up the radio and headed out excitedly towards South Beach. As we drove towards the coast, we passed by Miami’s intricate and vast skyline of luxury high rise towers that made Minneapolis' new construction of multi-colored and multi-façade buildings look like eye sores. As soon as we arrived to Miami Beach, the energy I had only seen in movies and music videos was all around us. We quickly dropped off our stuff at the hotel we were staying at for the night on Ocean Drive and made a bee-line for one of the many open air cafes to fuel up and then headed straight for the beach. For the remainder of the day and evening, we took in the indescribable energy of South Beach through its food, beaches, Art Deco architecture, colorful crosswalks, vibrant culture and even Bosnian cuisine at Rakija Lounge. This place had it all!
The next morning, we packed our things, put on our beach best excited to put the drop top down and finally hit the road. After multiple beeping errors and warnings in Spanish, we finally figured out our suitcase was too big to close the trunk. After almost giving up on the retractable roof idea, we finally figured it out and were on our way down old US Highway 1. This is where my romanticized idea of what the drive is supposed to be like is faced by reality, or more like slammed by reality. The first leg of the trip, which turned out to be over an hour just to get outside of Miami proper, was a wind-whipped and sweaty one-hour mile drive down a busy multi-lane road surrounded by the sounds of honking and fuel exhaust. To top it all off, our Miami Dance tunes were completely drowned out by a loud motorcycle directly in front of us that seemed to be conveniently headed in the same way. If I could leave you with any tips so you don't make the same mistakes as we did, it would be this:
Tip 1: If you rent a convertible (and you definitely should), keep the top up until you hit the Upper Keys, which can take up to a good hour and a half.
Tip 2: Along that note, if you rent a mini cooper convertible, make sure to only bring one small suitcase, otherwise get ready to cradle your belongings in your lap.
Tip 3: Miami has tolls, so unless you want to find out a couple months post trip that you have some new fees, make sure to avoid them or pay ahead of time.
As the Miami landscape disappeared in the rear view mirror, we finally began cruising along what is the official start of the Overseas Highway and I started to enthusiastically prepare myself for what I thought was going to be a scenic palm tree lined road ahead.
The Upper Keys ✧ Marathon, Florida
If being fully transparent, I was slightly disappointed when we hit the Upper Keys. Instead of the retro Beach Boy vibe we expected, we encountered mile after mile of strip malls and fast food restaurants and tacky souvenir shops. We decided to keep driving till we hit Robbie’s Marina where we stopped for lunch and to feed the giant tarpon.
From there, we headed to the Middle Keys where we finally transitioned into the more picturesque backdrop of palm trees and ocean vistas we were so excitedly hoping for. We were back in our happy place, wind in the hair, jamming out until - our car sputtered and started to crap out on us. Sitting on side of the road, the car rental company informed us of news that the particular mini cooper convertible we had was on recall and that we'd better not drive. We decided to cross our fingers and drive the remaining 7 miles to Marathon where we had a little tropical cottage waiting for us. We rented a couple of bikes and rolled our way to a white sandy beach that was surprisingly empty. Peace and paradise, at last! It was at this point that we started to wonder about the cost of real estate in the Keys and what it would be like to go to work in flip-flops and shorts every day. From what we learned from talking to a few locals, as long as you show up to work every day for a month, you get a raise and a promotion. Apparently, many locals suffer from something called the Keys Fever. ツ
We ate our way through Marathon's local seafood markets, inhaled delicious key lime pie, met a dog by the name of Captain Jack and mingled with the locals.
The next day, a new car was waiting for us and we continued our journey south. We were initially going to bike to the famous Seven Mile Bridge, but the park was closed for construction and it was raining out. Instead, we grabbed Cuban coffees (why had no one told me about this tasty goodness of pure sweetness?!) and headed to our final destination. As soon as we hit the Seven Mile Bridge, the clouds parted and sunshine came out. This was finally our wind in the hair, Thelma and Louise pure joy moment of the road trip. Teal blue water left and right, music blasting through the wind and dozens of tiny islands and sand bars dotting in the vast blue ocean. This is the moment we were waiting for, at last!
The Lower Keys ✧ Key West, Florida
An hour or so later, we found ourselves at our final destination and Florida’s southernmost point, Key West where we headed straight for the beach. Lying just roughly 90 miles north of Cuba, this tiny and mesmerizing island city is filled with pastel-colored historic homes, colorful facades and crosswalks, rum bars, and palm tree lined streets where roosters and chickens are the far most famous pedestrians and dwellers in town. We stayed at the Cabana Inn right off historic Duval Street and spoiled ourselves with delicious treats, fresh fish, and of course the best key lime pie. Unlike the rest of its counterparts along the Keys, Key West was unlike the rest and the perfect place to end our 3-day road trip.
Ending the trip in Little Havana + Wynwood Walls ✧Miami, Florida
Before heading back home to Minneapolis, we decided to cap things off with one more night in Miami. Arriving back to civilization and hungry from our road trip, we stopped in Little Havana to try the famous Cuban fritters, which did not disappoint and topped it off with afternoon Cuban coffee. Before going back to South Beach, we took one last detour and found, among all the vastness of concrete of Miami City, the vibrant and colorful walls of the Wynwood Arts District. Wynwood Walls is an outdoor museum showcasing large-scale works by some of the world’s best-known street artists. All the surrounding streets have been converted into funky art galleries, stylish bistros, late-night bars and breweries. You can’t help but feel happy surrounded by all the colorful murals.
We decided to spend our last night and a half-day before our return flight at a different part of South Beach, near Lincoln Road Mall – a pedestrian promenade lined with chic shops, sidewalks cafes, bars and art galleries. We were upgraded to a cabana room at the National Hotel, which boasts South Beaches longest infinity-edge pool. The next morning, we woke up bright and early while the rest of Miami was still sleeping from a night of partying to enjoy a dip in an all-empty pool and spent the rest of the day enjoying poolside cocktails before it was time to head back to the airport. Feeling slightly day drunk and tipsy from a whirlwind five days in the Keys, we headed back home to Minneapolis realizing that even when the slightest of things don’t go according to plan or some pre-conceived ‘vision’, that in the end, all that matters is the time spent with your best friend.