Four Days in the Florida Keys

Four Days in the Florida Keys

In late February of 2020, I took a trip to the Florida Keys. It was two weeks before shelter-in-place orders went into effect in California in March, and I remember when I arrived home and landed in San Francisco airport feeling like oh wow, this is getting serious. The next week we were all mandated to stay home. Talk about a pendulum swing, from feeling the total freedom of exploring magical islands to the restrictions of a hometown lockdown.

It’s been a full year since my trip to the Florida Keys. I’ve been to a lot of special places on this earth, but there’s some sort of magical dust that floats through the air and makes the atmosphere in the Florida Keys extra appealing. It’s not just the location, it must be something to do with the history of the region and the cultures that mix in that part of the world.

The Florida Keys are a series of coral archipelagos in the southernmost part of the continental United States, they get their name from the Spanish word cayo, meaning small island. I covered a lot in four days there, spending most of my time exploring Key West and one day making the long drive to Key Largo and back.

On arrival, the laid back vibe of Key West was instantly apparent. I dropped down in Key West just a few hours before sunset and headed to Mallory Square. I was greeted with the sounds of steel drums and slack key guitar and the most amazing sunset.


Key West is small and easy to navigate, most people get around on a bicycle, scooter, or on foot. The sounds of coastal breezes in the swaying palm trees paired with the whirring of air conditioners was the background music I heard as I explored. Here’s a glimpse of what I saw and few of my favorite stops.


Duval Street is famous but filled with tourists. It’s lined with shops and bars and I didn’t enjoy it very much during the day because of the crowds…



…  it’s much more fun in the evening when it’s balmy and you can enjoy live music while you sip a rum drink.

Mallory Square is a popular destination for the sunset, but equally appealing is the seaport walk along the harbor with all the boats and open air restaurants located along the meandering wharf, all playing live music.

I stopped in to see the Ernest Hemingway House and really loved the architecture, especially the second story wraparound porch. Lucky Ernest to live in such a beautiful home! Below is a picture of his personal office. He loved cats and I spied about a dozen on the property!

Taking a self guided tour of the Key West Cemetery in the Old Town is a thing, it’s there you’ll find a lot of history and a few comical gravestones.


Another worthwhile stop was the Butterfly & Nature Conservatory, walk around inside where exotic birds and butterflies are flying all over and don’t miss the cute flamingo couple in the middle.


What about the other Keys? There are so many! I’ve always wanted to drive this highway between Key West and Key Largo so I spent a full day on a road trip back and forth. It’s 100 miles from the 0 mile marker in Key West to Key Largo.

I was feeling ambitious so I drove from Key West to Key Largo in the morning and all the way back to Key West in the evening. I didn’t get to see and do everything the other Keys have to offer, but I stopped at several famous spots. Much of the appeal for me was just driving the highway, it’s something I’ve always wanted to do!

I rented a car in Key West then I drove to Key Largo enjoying the morning views over the Seven Mile Bridge and arriving two hours later in Key Largo for an early lunch at Mrs. Macs, located at the 99 mile marker. There are two locations, I chose the larger one and it’s true they have the tastiest fish (get the fresh catch!) and it’s there I developed a serious crush on the floor.



My next stop after lunch was to feed the tarpons at Robbies is Islamorada at mile marker 78. Pay a few dollars and head out to the docks to feed the tarpons, they are huge! But watch for the pelicans, they’re swarming everywhere and very greedy. Robbie’s also offers boat rentals if you feel like a water adventure and there are artisans on the property selling local goods.


I stopped in Islamorada to spend the afternoon, to see Morada Bay, and to visit the local art shops. It’s here where I photographed this art print which I named ‘Serenity Now’ because… obviously. 🙂


Across the highway I stopped in for a taste at the famous Florida Keys Brewing Company with its very colorful and creative interior. I loved their rainbow resin countertops and now I want a BEER sign made with bottlecaps too.



I wanted to make it to the Sunset Grille at mile marker 47 in Marathon Key for dinner and a sunset. It sits right at the edge of the Seven Mile Bridge. I arrived early because it’s a popular place with swimming, great food, live music, and a view of the bridge. I stayed for almost two hours I loved the vibe so much, and wow what a sunset!

I left after sunset and made it safely back to Key West that evening. It was a 200 mile road trip but what an incredible day!

I spent my last day biking around Key West but having to pause every minute because…. the real estate. I can’t even with the island style homes and their bright colored shutters surrounded by lush plantings and swaying palm trees. Dreamy!



Lodging is really expensive in Key West but I found a budget alternative. I stayed in a shared female bunk room at NYAH resort and just stored everything in a locker. It was perfect, they had a pool, free bicycles, and breakfast every morning and the hotel is centrally located within walking distance of everything in Key West.


So that’s my glimpse of a trip to the Florida Keys, it was such a fun place to hang out and I can tell it’s an amazing place to live! The Keys captured my heart, I look forward to a return someday.

My next trip to Florida will be a road trip along the Gulf to see Fort Myers, Marco Island, Naples, Bonita Springs, Sanibel Island, Clearwater and St. Pete, so if there’s anyplace I should stop on that road trip, let me know!