Road Trip Series: Key West, Florida.

December 23, 2015

The best places on Earth are the ones you have to trek, strain and sweat to get to. Key West had unexpectedly become that place for us after 12 hours of driving from Atlanta, Georgia to Key West, Florida. City streets turned to interstates which opened up to the vast Everglades, and when the sun began to set we hopped our way from island to island across the keys at a slow and steady 25 miles an hour. Torture. Pure torture.

When we finally rolled into town right around 1:00 AM, I knew this place was different. People were zipping around the streets on mopeds, hollering at their friends up ahead in golf carts. A soft summer breeze blew the palm trees that lined every street and in the eery quiet of the night I could faintly hear, almost just sense, that the city was still awake. Somewhere the ocean lapped at the shore, so gently I couldn’t hear it, but I could smell the brine.

Key West, Florida.
Southernmost Mansion, Key West, Florida.

Key West is the southern most city in the United States, therefore many of the hotels have “Southernmost” in the title. I had booked the hotel only a few days before since we were on a road trip and didn’t know the exact days we would be there. In the haste, I had booked at one hotel but saw the picture of another “southern most” hotel. We arrived at the “Southernmost Mansion”, which was an enormous, wildly colorful and eccentric mansion that was clearly closed at this hour. After making a few phone calls and waiting, aching and dozing on the front steps, we discovered that we were not at this Southernmost. We were at the “Southernmost Beach Resort” across the street…WOW. An hour later we were settled into our beautiful pool view room, showered, and crashed on the bed. Our Key West adventure had begun.

Key West, Florida.
Key West, Florida.

Key West is hot. I mean, boiling hot. In July it feels like the surface of the sun and unlike most resort towns, the southernmost part of Key West does not have many great beaches. The one connected to our resort was very tiny. There was this weird tidal thing happening as well so there was a lot of seaweed and it smelled like stinky feet at low tide. Our solution? Stay in the pool and drink all day.

The first day we did exactly that. The Southernmost Beach Resort had three pools;  a large one near the beach, spa and bar, another one right below our room and a small heated, adults only pool that I unfortunately only discovered the last day of our stay. We floated and bobbed around, drink in hand, until our toes were raisins and our livers were asking to take a break.

Southernmost Resort, Key West, Florida.

The farther south we traveled the more I struggled to kick my Manhattan fashion habits and opt for a more casual and comfortable style. In Key West I left behind my heels and slid into sandals, loose jeans and a breezy crop top to wander the streets at night and discover what Key West offered when the hot hot sun went down. We headed inland away from the ocean and discovered bars, restaurants, street food, smoothie shops, art galleries and old churches. We found a tapas place with seating on a front porch under a drift wood lamp. That night I will never forget, because we sat together and talked about how much we accomplished on this road trip. How it wasn’t easy but we pushed ourselves and we were so glad we did.

Key West, Florida.

It was hard to believe the days could get any hotter but they did. My dad is a huge Ernest Hemmingway fan so I promised him I would visit the authors house. You had to keep moving or you would melt into a puddle of sweat and burnt skin. I zipped through the house and absorbed everything as fast as I could because that day was oppressive. I learned that Hemmingway was a big time cat lover, and cats descended from his first cats still lived on the property. They looked down at you as you walked around their old masters house, and all the ones that have died were buried in the back yard with hand paid tombstones. We were going to explore more but it got so hot we said F it, let’s go back to the pool!

Southernmost Point, Key West, Florida.
The Southernmost Point in the Continental USA, Key West, Florida.


Key West we considered our time to relax, drink and enjoy some well deserved rest together. Our last day we stood on the southernmost point of the continental US and tried really hard to spot Cuba (90 miles away and yes, impossible to spot). We read and napped by the heated pool, ate lunch and watched baseball, and enjoyed some drinks while we planned the next leg of our adventure. In the midst of unwinding from the first leg of our trip, I didn’t realize how at home I felt there; it was weird and the people were different. There was art and music, great food and rich history. I would go back in a heart beat…just maybe not by car next time.


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