Island hopping by car in Florida Keys a unique road trip

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Published: February 8, 2024

The Overseas Highway and 42 bridges connect 44 islands in the Florida Keys. | Robin & Arlene Karpan photo

It’s a road trip like no other in North America, where we seem to drive over as much water as land. The Overseas Highway route extends more than 180 kilometres through the Florida Keys, a string of islands stretching in a southwesterly arc off the tip of Florida. Along the way, we cross 42 bridges connecting 44 islands surrounded by turquoise blue water.

Most impressive is the Seven Mile Bridge, spanning seven miles of open water. When completed in 1912, originally for train traffic, it was considered an unprecedented engineering achievement. At tiny Pigeon Key next to the bridge, an historic site tells the story of those early years of construction, when workers living on the five-acre island had to contend with everything from constantly sinking into sand to crocodiles, snake bites and heat stroke.

A new bridge has since replaced the original Seven Mile Bridge, with a section of the old one recently opened to bikes and pedestrians. It’s a rare opportunity to go hiking over the ocean.

While the Keys might seem like an extension of the Florida mainland, their subtropical climate and landscape of coral and limestone make them more like Caribbean islands.

Brown pelicans hang around the wharf at Islamorada Key. | Robin & Arlene Karpan photo

Each island has a different specialty. Key Largo, the most northerly, is known for diving and snorkeling on nearby coral reefs. Islamorada stands out for sport fishing for marlin and other deep sea specialties.

The most southerly road-accessible island, Key West, measures only two by four miles in size, and is closer to Cuba than the Florida mainland. In the late 1800s, it was the richest place in Florida, with fortunes built almost entirely on salvaging shipwrecks. Improved navigation eventually ended that industry.

Like the rest of the Keys, the economy today depends entirely on tourism. The island boasts a combination of a rich history preserved in Victorian-era architecture, an inviting tropical setting and above all a quirky nature with an anything-goes attitude.

One of the first things we notice are chickens wandering everywhere. It’s not unusual to hear roosters crowing in the middle of the small city. They were brought from Cuba years ago to be used for cock-fighting. When it became illegal, the abandoned birds went wild. They also thrived. Today, wandering chickens are just considered part of Key West’s special ambiance.

A visit to Ernest Hemingway’s house provides a literary diversion. | Robin & Arlene Karpan photo

A lot of famous folks called Key West home, including writers such as Tennessee Williams and Robert Frost, and President Harry S. Truman, who spent the winters in his “Little White House” to escape the Washington cold.

But the personality that looms largest is Ernest Hemingway, who lived here for a decade in the 1930s and wrote many of his famous novels such as For Whom the Bell Tolls. We can visit Hemingway’s favourite watering hole, Sloppy Joe’s Bar, which is still going strong in large part to its connection with the famous writer. They even hold an annual Hemingway look-alike contest.

Hemingway’s spacious Spanish colonial house built in 1851 is a museum where you can wander through on your own or take a guided tour. His old typewriter still sits on the table in the writing studio.

In keeping with Key West’s eccentric nature, an estimated 50 or more cats have the run of the house and grounds. It started when Hemingway was given a six-toed cat by a sea captain, and it is believed that most of these are descendants.

Dolphin watching excursions are a popular activity. | Robin & Arlene Karpan photo

Boat excursions are popular, especially sunset cruises by sailboat to where the Atlantic Ocean meets the Gulf of Mexico. A boat trip we liked even more was a dolphin watching excursion to an offshore area known as the Dolphin Playground, with shallow water next to mangroves where dolphins like to fish.

It wasn’t long before we had dolphins swimming beside the boat. They love playing and even treated us to a few spectacular leaps out of the water. Dolphins are a mainstay of many aquariums and marine parks, but nothing compares with watching them in the wild.

Dolphin watching excursions are a popular activity. | Robin & Arlene Karpan photo

No visit is complete without sampling key lime pie. While popular throughout Florida, here it borders on being a religion.

Somewhat similar to a lemon cream pie, it is made with key limes, which are smaller and more flavourful than regular limes. Debates rage as to whether it is best topped with meringue or whipped cream and how sweet or tart it should be. They are sold everywhere, and no one will bat an eye if you order pie for breakfast.

Arlene and Robin Karpan are well-travelled writers based in Saskatoon. Contact: travel@producer.com.

About the author

Robin And Arlene Karpan

Robin And Arlene Karpan

Robin and Arlene Karpan are well-travelled writers, photographers and book publishers based in Saskatoon, Saskatchewan, Canada.

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