Stringing Together the Florida Keys

Because our journey to Cuba would be launched from Miami, my husband and I had an opportunity to fulfill another long-held desire: to drive the scenic coastal highway along the Florida Keys. Although we had been to Florida several times before, we had never tacked the time onto our vacation necessary to make the journey. This visit though, we added a few days to explore the area, which had the additional benefit of allowing us to acclimate ourselves to the three-hour time zone difference before we reached our main destination.

Although I was aware that the Keys – and especially Key West – had become a bit of a tourist trap, I still wanted to see them for myself. I was intrigued by pictures of turquoise waters and distinctive architecture, fascinated to read about the time Hemmingway spent in Key West, and inspired by the romance of the many songs written about this beautiful necklace of islands along the coral archipelago.

There are more than 800 islands that make up the Keys but fewer than 50 of these are inhabited (“Key” is derived from the Spanish word Cayo which means small island).  The Overseas Highway that stretches from Key Largo to Key West is a series of causeways and bridges — including the spectacular Seven Mile Bridge – and provides plenty of vistas along the way. It was built to replace the Overseas Railway that was constructed in the early 1910s and then destroyed by a category 5 hurricane in 1935. It takes about 3 – 4 hours to drive the 110 mile route, depending on traffic and the number of stops needed to admire the scenery and, of course, to grab a cheeseburger in paradise.

We only had two days set aside for our visit and, looking back, we should have allowed for more. There is a lot to see and do on these beautiful and captivating little islands.

Hemmingway's house and museum is home to 40 - 50 polydactyl (six-toed) cats
Hemingway’s house and museum is home to 40 – 50 polydactyl (six-toed) cats. If you look closely, you can see Truman’s “thumb”
The study in Hemmingway's Key West home
The study in Hemingway’s home, where it is said that he wrote “To Have and Have Not,” a novel about Key West during the Great Depression
In Key West a marker indicates the southernmost point in the continental U.S. (just 90 miles from Cuba!)
In Key West a marker indicates the southernmost point in the continental U.S. (just 90 miles from Cuba!)
Sailing into the sunset
Sailing into the sunset off the shores of Key West
The crowd at Mallory Square gathers to watch the sunset
The crowds at Mallory Square gather each night to watch the sunset
After the sun set, the crowd applauded and disbursed, unaware that the best part of the sunset occurs several minutes after it disappears below the horizon
After the sun set, the crowd applauded and disbursed, unaware that the best part of the sunset occurs several minutes after it disappears below the horizon

Author: Janis @ RetirementallyChallenged.com

My blog is about travel, relationships, photography, and whatever else pops into my head (even, sometimes, issues surrounding retirement and aging).

14 thoughts on “Stringing Together the Florida Keys”

    1. I hope you allowed more time than we did! There is so much to see and do! Make sure you get off Duval Street – it’s a lot of fun but the “real” Key West is on the side streets and down the alleys. Have fun!

  3. Hi Janis! Thom and I took that trip back in 1990 and some of it still looks the same. And yes, of course we took the same looking photo at the Key West marker and watched the sunset from the same point. Great place to visit and so much fun. Thanks for the memories! ~Kathy

    1. I don’t know if we’ll ever get back to Florida but, if we do, I hope we can go down to the Keys again. California has the beach and the weather, but there is something about the rich history and colorful Caribbean vibe of the Keys that is so magical.

  4. Thanks for sharing. While from North FL, I have never been to the Keys. I need to remedy this, especially since I am fond of the movie “Key Largo.” All the best.

  5. I’ve done this trip several times. That highway to Key West is awesome. There are points where water is lapping on both sides. The cats are fabulous. Last time we were down there was a big controversy with chickens. They were allowed to roam freely around the town and some people were trying to stop that. We were last down in February a decade ago and I was surprised how cool it was. Don’t think we ever got higher than 70 degrees. It’s way more historical than you think it will be and I really enjoyed the Hemmingway lore.

      1. Good for the chickens. I remember the cost too. We stayed at a “discount” room at the big Hilton. I was not happy. It was tiny and the windows were by a walkway where everyone could look in so we had to keep the drapes closed. I swore next time I would be in one of the suites that looked out on the gardens. I think we did about 5 days or so. It wasn’t a full week. Good Cuban food. Anxious to hear about the food in Cuba.

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