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Drive through the Keys

The three hour drive through the Florida Keys is surely America's most unique motor journey. No other place in America combines the scenic ocean views of the Overseas Highway with a local community that is proud to show off its history and natural wonders.

Key Largo is the first island you will see as you enter the 110-mile Florida Keys chain.  It is our longest island and the one where Humphrey Bogart and Lauren Bacall battled Edward G. Robinson and a hurricane in the 1948 gangster movie “Key Largo.” 

Today, visitors can take a tour on The African Queen, the boat Bogart and Katharine Hepburn fell in in the 1951 movie, “The African Queen,” which is set in World War I Africa.

After Key Largo you will reach Islamorada, a village of homey islands that includes Windley Key, Upper Matecumbe Key and Lower Matecumbe Key. Morada means purple in Spanish, and lore has it the early Spanish explorers named these isles for the floating purple sea snails, or janthina janthina, they probably saw feeding on jelly fish near the islands.

Two offshore islands here have special pasts. On Indian Key, you can see the site where early settlers were attacked by raiding Indians. Set foot on Lignumvitae Key and your are walking on an ancient, modestly elevated patch of land where tropical hardwood trees, including the lignum vitae, have taken root. Both islands are accessible only by boat.

Islamorada also prides itself as the Sportfishing Capital of the World. Here, you can venture offshore on a charter boat for a chance at the beautiful, acrobatic sailfish or the magnificently colored Fishingdolphin fish, a.k.a mahi-mahi. Hire a guide and you can take to the shallow near-shore waters to catch the mysterious ghost of the flats, the bonefish, or venture into the backcountry to catch redfish and tarpon.

Keep heading southwest from Islamorada, and soon you will see Long Key State Park. Here, you can walk through undeveloped tropical forests that are representative of the Keys wilderness of a century ago. Get back on the road and you will come to Grassy Key. At the Dolphin Research Center here you will have a rare opportunity for one-on-one contact with these intelligent mammals.

Next, you will reach Marathon, a small city at the mid-point of the Florida Keys. Nearby is Key Colony Beach, a beautiful village of quaint homes and marinas. If golf is your game, you’ve come to the right place. Both Marathon and Key Colony have excellent courses.

Marathon at the heart of the Florida Keys is also home to Crane Point Hammock. This 64 acre reserve is some of the most historically and archaeologically-rich land in the Keys. Pre-Columbian artifacts have been discovered here, and the site is home to the Museum of Natural History of The Florida Keys and the Children's Museum.

After Marathon, you will reach the foot of the Seven Mile Bridge which is the gateway to the Lower Keys. Don’t pass up the small island below the bridge. Pigeon Key once housed the workers who built Flaglers' railroad in the early 1900s. Today, you can take a tour of this island and view a snapshot of life in the early 20th century.

After the Seven Mile Bridge, the vast sweep of the Straits of Florida and the Gulf of Mexico can easily be seen from Bahia Honda Bridge. Stop at the state park here and you can experience a beach that is frequently listed as one of the most beautiful in the United States. It’s easy to see why the Keys are recognized as America's Caribbean Islands.

Big Pine Key and the rest of the Lower Keys are next. Big Pine is the jumping off point for Looe Key, a shallow coral formation that is one of the most spectacular shallow water dive locations anywhere. Big Pine is also home to the diminutive Key deer, a subspecies of the white tail deer. There are even a few alligators in a pond nicknamed the Blue Hole that’s tucked away in a pine and palm grove.

Keep exploring and before long, you’ll find yourself in Key West, the final stop on the Overseas Highway. Here, the land meets the sea amid 19th-century charm and 21st-century attractions. This is the nation's southernmost city, and it is actually closer to Havana than Miami.

Stop the car and take a stroll amid the tiny, colorfully-restored homes where thousands of cigar workers lived in the 19th century. You will also see huge mansions that were built by business tycoons and city leaders. Some have been converted into guest houses and inns with modern swimming pools and lush tropical gardens.

Stop to chat with the locals and you might come across one of the native-born Key Westers, who call themselves Conchs. Be sure to ask the Conchs about the Key West of their childhood, from the tropical fruit trees in their yards to the namesake shellfish they gathered in the shallow near-shore waters.

You can easily see why novelist Ernest Hemingway found inspiration for some of his best work here. Hemingway purchased a pre-Civil War mansion on Whitehead Street in the 1930s and lived in it for nearly a decade. These days, thousands of visitors seek out his home which is now a museum.

Treasure hunter Mel Fisher also called Key West home. Using Key West as a base, he recovered millions of dollars worth of gold and silver from the ship Nuestra Señora de Atocha, a 17th-century Spanish galleon that sank 45 miles west of Key West. Years before he died, Fisher had the good sense to establish the Mel Fisher Maritime Heritage Society Museum, where visitors can view and even touch some of the riches of the Atocha and the Santa Margarita.

If you’ve timed your drive right, you’ve reached Key West just in time for sunset. Visitors and local artists gather on the dock at Mallory Square each evening to celebrate the end to another tropical day. Musicians, jugglers, mimes, and the occasional fire-eater entertain you while local food vendors keep you fed. The daily sunset celebration has become one of Key West’s greatest traditions.

After sunset, the fun is just beginning. When the night falls, chances are you can find a restaurant or watering hole to meet your tastes. Many bars offer live music, including New Orleans-style jazz and local tropical creations. If you like plays or musicals, you’re in luck too. Key West has several small theaters that showcase performances by local acting troupes. And the island even has a symphony now.

When you lie down at the end of the day, you’ll realize the drive was worth it.