Road Trip Through the Florida Keys

The most dramatic drive on the East Coast, from party-hearty Key West up to the Everglades

Key West Beach in Florida

Key West Beach in Florida

(Typhoonski /

The Seven Mile Bridge

(Steve Giralt)

Day 1: Fort Myers beach to Key West

Two years ago my parents began participating in the migratory patterns typical of many northerners, making seasonal peregrinations between Canton, Ohio, and Naples, Fla. During visits south, as I drove past one gated community after another, I often wondered where I might find more of the colorful Florida that occasionally peeks out from behind the condos. So I proposed a road trip to another part of their adopted state: the Keys.

We start not in a car, but in a boat--Key West Expressoperates a high-speed catamaran service from Fort Myers Beach. A short walk beyond the Key West Ferry Terminal brings us to Mallory Square, a wide plaza at the foot of Duval Street, Key West's main road. Lined with Victorian mansions and late-19th-century commercial buildings, Duval is a picturesque thoroughfare pocked with rocking-loud bars. In a shop window, I notice a T-shirt emblazoned with THE LIVER IS EVIL. IT MUST BE PUNISHED, which seems to sum up many visitors' philosophy.

A quieter side of Key West is immediately apparent when we turn onto Petronia Street, heading into the Bahama Village neighborhood. AtBlue Heavenrestaurant, in a courtyard that was the scene of boxing matches during the Depression, tables sit under a canopy of trees, a balmy breeze stirring their leaves, and at least a half dozen of Key West's free-roaming chickens scratch around for crumbs. (More on them later.) The special is a lobster melt--yes, it's like a fancy tuna melt--and it sounds too good to pass up. A beer for both my dad and me and a margarita for Mom also seem appropriate. When in Rome . . . 

Walking off lunch, we stumble upon theKino Sandalsfactory, founded by two Cuban refugees in 1966. It feels like old Havana. Ceiling fans churn languidly while men and women hunch over workbenches making stylish leather sandals, none of which cost more than $13 a pair.

There's just time to catch the last tour atThe Little White House, an 1890 house on Key West's former naval base. Harry Truman vacationed there 11 times during his presidency. Our guide, a real Truman buff, leaves us all but humming "The Star-Spangled Banner," feeling immense pride in a country in which a plain-spoken haberdasher from Missouri could become thepresident.

Evening is settling in as the crowds wander toward Sunset Celebration at Mallory Square, a daily event since the '60s. We grab a margarita from a stand and wander among the crowds and street performers. The sunset takes 20 minutes, and then we head back to our hotel for a swim. TheChelsea House, our B&B, is in a converted Victorian house surrounded by a garden that makes it feel private and tranquil, though it's just a stone's throw from Duval Street.

We have dinner atB.O.'s Fish Wagon, an old truck and a shack in a corner of a parking lot in the historic seaport section of town. The fish sandwiches, on Cuban bread with key lime sauce, are legendary for a reason. Afterward, we look at the boats, decorated with Christmas lights for the annual parade and competition.



  • Chelsea House Pool & Gardens709 Truman Ave., Key West, 800/845-8859,, no guests under 16, from $99


  • Blue Heaven305 Petronia St., Key West, 305/296-8666, lobster melt $14
  • B.O.'s Fish Wagon801 Caroline St., Key West, 305/294-9272, fish sandwich $8.75


  • The Little White House111 Front St., Key West, 305/294-9911, $11


Day 2: Key West to Marathon

Breakfast at the B&B is basic--coffee, pastries, and fruit--so we head to the French-inspiredBanana Cafefor omelets and cafés au lait. The restaurant has taken over the ground floor of a yellow house done up, like most buildings in Key West, with gingerbread woodwork. Tables spill out of French doors onto a wide porch. From ours, I spot a sign forThe Chicken Storeon a semi-decrepit shotgun cottage.

Approximately 2,000 feral chickens meander around the island, descendants of birds brought by the first settlers in the early 1800s. The store, which raises rescue money by selling T-shirts and artwork celebrating the chickens, was established "to smooth the sometimes-rough relations between man and bird in Key West." It's also a sanctuary where ailing chickens recuperate in relatively posh surroundings. I'm glad I'm not wearing sandals, since some of them like to peck toes. The store even ships the birds anywhere in the country as a "living souvenir." (It's also since moved to Homestead). 

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Note:This story was accurate when it was published. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.

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