Footloose & Car-Free
Slam the car door shut and grab your favorite walking shoes. With its quaint, narrow side streets and bustling traffic, Key West's Old Town, approximately one by 1.25 miles, begs to be explored on foot. Nearly Caribbean, the island is known for its renegade attitudes and good times. Should you tire of ten-toeing it up and down the historic district's streets, you can rent bikes (provided free by some accommodations), surreys and electric cars or hop aboard the sightseeing trolley or Conch Train.
In a car, we would have missed the guy biking down Duval Street with a dog hanging onto his neck piggyback-style. We would not have heard the dude drumming jazzy rhythms on upside-down plastic paint buckets or our stomachs growl at the aroma of frying conch fritters.
It works out well that some of the island's best resorts encroach on Old Town boundaries, including Hyatt Key West Resort and Spa, Ocean Key Resort and Spa, Pier House and Carribean Spa, and Sunset Key Guest Cottages, a Westin Resort, just a shuttle-boat hop away from Mallory Square.
The heart of Old Town, and at sunset the pulse, Mallory Square turns into a nightly street fair as the sun begins to set. Jimmy Buffett wannabes, fire-eaters, artisans, conch-fritter vendors and sun-tinted tourists converge to get the nightlong party going.
Walk This Way
You can find most of the action on an eight-block stretch along Duval Street from Mallory Square. Besides the famous and infamous clubs, bars and taverns - Sloppy Joe's, Margaritaville and others - that spill their music and frenzied crowd into the street, restaurants funky to fine keep up the momentum for those exploring on foot. Plus, there are some unusual attractions such as Ripley's Believe it or Not!.
Side streets off Duval hold still more surprises: The Harry S. Truman Little White House, where presidents from Taft to Clinton have stayed; the former ticket office of PanAm airlines, now a Caribbean restaurant and micro-brewery restaurant named after Top Gun actress Kelly McGillis; a Bahamian "Conch" (native Key West) village where orange-feathered chickens wander the streets; the Key West Shipwreck Treasure Museum, devoted to a heritage of wreck salvaging; a factory that sells inexpensive sandals off the assembly line; and corner shops carrying everything from cigars and sponges to thong bikinis and gold doubloons.
Take Front, Greene or Caroline Street to just north of Old Town proper, where the Historic Key West Seaport area presents a salty scene of seafood shacks, boat tours, water sports rentals and specialty shops.
Wander to the island's east side along Whitehead Street and you come across some of Key West's most celebrated attractions, including the classic Key West Aquarium, the Ernest Hemingway Home with its six-toed cats and the climbable Key West Lighthouse and Keeper's Quarters Museum. Even the Southernmost Point in the U.S.A. and the island's beaches are within a half-hour's walk from Mallory Square. Stop at Fort Zachary Taylor Historic State Park, off Southard Street, for a beach break and history lesson. Continue on to Higgs Beach, the White Street Pier and Smathers Beach, another good place to get into some water sports.
Stop in for liquid refreshment at Sun Sun, the beachside, poolside bar at historic Casa Marina, a Waldorf Astoria Resort. Return along Passover Lane, taking a moment to pay respects and score some chuckles off the quirky headstones at the Old Town Cemetery. At Eaton Street, you've come full circle. Stroll the residential streets to get an eyeful of the distinctive architectural approach that has come to be known as Key West style, homes built at the turn of last century by shipwrights and crowded by greenery and blossoms as vibrant as the paint jobs. Many of the oldest have been turned into bed-and-breakfasts and inns, including Curry Mansion Inn, Cypress House and Heron House.
Footloose & Car-Free