This is a leisurely itinerary, designed to follow a busy day in the Old Town, and your walk will be broken by a slow and pleasant lunch. Head toward the southern end of Old Town, near the middle of Whitehead Street, where you will find Key West’s Bahama Village.

Bordered by Angela, Petronia, and Olivia streets, Bahama Village is an old Key West neighborhood where many descendants of the city’s earliest Bahamian settlers and West Indian slaves still live. During the 18th century the Bahamian incomers utilized their knowledge of tropical architecture and plants to help make Key West what it is today.

From the outside, the neighborhood appears weather-beaten and run-down, full of small wooden homes that look as if a strong wind could blow them away. But underneath those tin roofs are walls and floors made of Dade County pine, a sturdy, almost invincible Florida hardwood.

Some of the homes are painted bright Caribbean colors of pink, blue, and green, with purple bougainvillea vines adding a further splash of color. Taking a slow morning walk through the streets, you feel as if you’ve been transported to the islands – the ones on the other side of the Gulf Stream, that is.

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As the topographical tail of the United States, Key West dangles off the end of the Florida Keys chain, an island of unfettered freedoms and capricious charms.

It is a nonchalant, end-of-the-road kind of place where people who never want to grow up feel right at home. It is crazy, indulgent, uninhibited and hip, full of small town gossip and big city panache.

The city’s architecture a blend of Spanish, Bahamian, New England and Southern is world famous, with grand tropical mansions adorned with gingerbread railings dotting even the most ordinary of streets.

The resident population a combination of old Conchs, rich yuppies, middle-class families, Cuban immigrants, Bahamians, military employees and gays totals about 25,000, but when you add the million tourists who visit each year, the island can feel very crowded.

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A stop at the Caribbean Club for an early morning Bloody Mary, followed by a visit to the African Queen, lunch at Mrs Mac’s Kitchen, and a late afternoon stroll through the Florida Keys Wild Bird Sanctuary. 

The Upper Keys are about a one and half hour drive south of Miami Beach, which makes them far enough from civilization to be a haven for escapees from Miami and Fort Lauderdale, but close enough to the mainland to still feel connected. 

They are a weekend warrior’s paradise, a place to run away to even just for the day. 

Critics of the Upper Keys say they are nothing more than a Miami Beach playground, but if so, they are a playground or unparalleled beauty.

Just south of Florida City, the Overseas Highway begins and the first mile marker appears MM126, which means you’re 126 miles north of Key West and heading straight for Key Largo. Read more »

South of Miami Beach, follow Highway 1 to reach the inimitable Florida Keys, America’s near-tropical islands. As they trickle farther from the mainland, the Keys become noticeably more removed from mainstream tempos and rules. 

A laid-back, quasi-renegade attitude takes hold. 

Dress is fishing-boat casual. Life revolves around the water. Time is told more by tides and sun than by clocks. Much of the waters around the Keys are designated marine wildlife refuges, providing the state’s most popular destination for diving. 

Kayaking, fishing, and lobstering also draw water enthusiasts. 

The Keys stretch for more than 100 miles, starting with Key Largo of film fame. This is the site of John Pennekamp Coral Reef State Park, which lies at the town’s north end, about 40 miles from South Miami Beach. 

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The 31 islands that make up the Florida Keys are linked together by a series of 42 bridges and dozens of causeways. 

They are divided into three regions: the Upper Keys, Middle Keys and Lower Keys. 

Overseas Highway, a sometimes tedious but always panoramic road, snakes its way through the entire island chain and comes to a dead end at the creme de la creme – Key West. 

Each of the three regions deserves at least one full day to explore and can obviously take longer if you have more time to spare. The itineraries we suggest highlight the principal places of interest, while following the Overseas Highway, and leave you to select the areas that most appeal to you. 

Except for Key West, which can be explored on foot, it is almost impossible to travel in the Keys without a car. The itineraries refer frequently to the mile markers, which is how distances are given and locations identified in the Keys. 

These have been highlighted in order to make the routes easier to find. 

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In April of 1982, after the Federal government set up a series of road- blocks in the Keys to screen for illegal drugs and aliens, outraged residents banned together in a mock public protest. 

It was not that they wanted to shelter illegal aliens or help drug traffickers, but they resented the intrusion. 

Hoisting a flag adorned with a conch shell, hundreds of Key West residents gathered in Mallory Square, ceremoniously seceded from the state, handed out passports, and declared their land the new Conch Republic. 

The celebration, done in jest with more than a hint of sarcasm, lasted for a week and has since become a popular annual event that reinforces the distinct island mentality of the Keys. 

This island mentality pervades every aspect of life in the Keys. 

Today, descendants of the original Conchs still call themselves by that name and relish their independence. Although dwindling in numbers, the Conchs (a true Conch is someone who was ‘born on the rock” of Key West) are granted a certain amount of respect in the Keys and are somewhat supercilious towards the many newcomers who revel in their new-found island lifestyles. 

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Although Key West had already become a tourist mecca in the 1930s, the post-war years and the 1950s brought a substantial increase in tourism throughout the Keys. 

The fact that President harry Truman spent his vacations at the Key West Little White house no doubt added to the area’s popularity. 

What was good enough for the president of the United States had to be good enough or many of its citizens. Slowly but steadily, more and more Americans began piling into their station wagons and making the long journey down Overseas Highway in search of sunshine, sea air and the other components of relaxing vacations. 

Mom-and-pop motels, fishing lodges and campgrounds sprouted up to cater to their needs, as did restaurants, souvenir shops, and marinas. 

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During the 1880s the American government poured millions into the economy and Key West became a boom town. By 1890, it was not only the largest city in Florida, but the richest city per capita in the United States. 

Although the wrecking industry had died out, it was replaced by other money-making endeavors, which were within the law and far less anti-social and dangerous than wrecking had been, although not without their long-term problems. 

Sponging was one of them, and for a while the waters off the Keys provided 90 percent of all the natural sponges used in the US. 

Another prosperous industry was cigar-making. 

A group of Cuban settlers, employing over 6,000 Cuban workers, created a virtual gold-mine by manufacturing their world-famous cigars that usually you can find also in Ocean Drive in South Beach from a nice Cuban girls. 

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