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Topless drive to Key West

Updated: Dec 15, 2023

During our week settling back into Miami after our 110 days at sea to explore South America in April, we had planned the obligatory topless drive to the Keys with our dear friends who were visiting from Brazil to the end of the road, as some may call it to transport ourselves into the homes and architecture of New England…

We are all too familiar with the long stretch of road that we see decorate the southern tip of Florida from the US box office hits we have seen over the years. The Keys are a coral cay archipelago, a string of tropical islands stretching about 120 miles off the southern tip of the U.S. state of Florida, between the Atlantic Ocean and the Gulf of Mexico. Would you believe you are just 93 miles from Cuba once you reach the end? Home to the third-largest coral reef in the world. The Keys are a destination for fishing, boating, snorkelling, scuba diving, vacations and retirement.

We were picked up bright and early in Miami by our friends visiting Miami from Brazil; spending time together again after meeting a few months ago in Santos while cruising Brazil's beautiful coast was precious.


Miami skies had decided to take a breather after three days of torrential rain, so it was the perfect day for a long drive.

Four and a half hours later, we arrived in Key West; the waters along the way were the classic clear turquoise, scattered with fishing boats and marine activity as we inched our way to the end. However, as we arrived in Key West, the four-by-two-mile island on the tip of the Peninsula, the hues had migrated into darker tones.

The buildings and homes were all charming and beautiful. Duval main street screamed tourism, and as we walked the hot paths in the midday sun, we soon realised it was going to be challenging to find the dining experience that we were hoping for, a beautiful seaside view restaurant with white tablecloths, a place you could sit back to relax and enjoy a slow lunch devouring delicious overpriced food and wine.

This dream of ours soon became a false reality, as all the culinary venues we hunted for only opened from 5 p.m. Still, you had an abundance of options with plastic chairs, paper napkins and casual-style bistros, pubs, and cafes to peruse. We settled on a simple place that also guaranteed air con to nourish our bodies and continue our way. With Key West being the birthplace of key lime pie, this was on the list; unfortunately, after consuming a burger, space was limited, so we had to bypass it.

With the impending long drive home, our friends stopped off for a tour of the Hemingway Residence whilst Wayne and I felt our USD36 for the entrance fee was better spent on an afternoon beverage. We enjoyed visiting a local hotspot, Moondog, to chat with the team and visiting regulars to learn more about the small town of Key West. This was tucked a street back from the heavy tourist Duval Street.

The sacred Rooster was of interest; as you drive into Key West, you oddly notice the colourful roosters roaming the streets and strutting through the traffic. The story goes back in the day when the chickens served their purpose as a source to provide an endless quantity of eggs and Sunday dinners for the residents, and cockfighting was also legal and was a favourite gambling activity of many southern men. The chickens started escaping the backyards and soon became known as the Gypsy Chickens around town. Then, in the late 1980s, when cockfighting became illegal, the Roosters were released to join them.


Key West chickens roaming the streets are descendants of jungle fowl originating in Cuba and the Caribbean islands. Due to the vital part, they played in keeping everyone with their daily nourishment, and the island has a no-kill policy, they are protected, and now the local mascot and you will find the rooster as inspiration amongst all the local designers from artwork, jewellery, clothing on and so on.

The Florida Keys definitely deserve an overnight stay and thorough research. We honestly went with the flow, which damaged the experience. To truly appreciate the vibe, you need to have a plan; there are more than 800 keys in southern Florida, and the coastline changes dramatically. Therefore, you might also find what you are looking for earlier in the road trip.

The locals were very friendly with lovely energy; the dining scene was focused on evenings, and with the live music exuding from most venues, the evenings were designed to provide a wonderful and lively experience for visitors.


We were blessed all the same to spend a day with our gorgeous friends and relish the moment we are both in the same city, the same country at the same time after only having met in Brazil a few months ago; our hearts are full 💛

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