By Chris McBeath

Lying at the southernmost point of the United States, just 90 miles north of Cuba, Key West rests at the end of a raffish string of islands that attracts all manner of souls whose hearts beat to a different drummer – fishermen, salvagers, ecologists, writers, poets, artists, and national leaders. Many of these folks are known only by their first name … which is exactly the way they want to keep it. After all, this is a place to escape to.

1. Duval Street

The busy and eccentric thoroughfare of Key West draws people-watchers galore. Most head for Sloppy Joes which is one of the more celebrated (ie: touristy) Hemingway haunts. For a more authentic experience, head across the road to Ricks, grab an outdoor stool, a pail of peanuts and get set to enjoy offbeat conversations with passers-by.

2. Sunset Celebration

About one hour before the crimson-orange sun sinks into the Caribbean waters, the waterfront promenade at Mallory Square becomes one sixties-styled festive love-in of street performers, popcorn vendors, artsy displays and musicians. Go early to secure your spot to watch the sharpening silhouettes of ships, parasailers and starry eyed lovers create some stunning Kodak moments.

3. Peppers of Key West

It’s billed as the hottest spot on the island with good reason. Look for the red pepper-mobile parked outside and expect to find fire-inspired sauces, spices and pepper-related paraphernalia galore. Titles that tell the tale include Dave’s Insanity, Capt Phil’s Wreck-Tum Fire, Colon Cleaner, and the house specialty, Goin’ Bananas, a terrific basting sauce made out of bananas, raisins, tamarinds, Worcestershire sauce and, of course, dynamite chilli-peppers.

4. El Siboney

This unpretentious café is run by mammas as generous in size as the platters of Cuban food they serve. It’s one of the best values in town, for appetites that aren’t for the faint of heart.

5. Key West Seafood

Although Mark Phillips is one of the area’s best charter captains, he turned his fishing savvy into creating the best seafood restaurant in Key West. The modest entrance belies what you’ll find inside: a romantic, open-air garden with secluded café tables tucked into gorgeous greenery complete with fountains, stone angels and pagodas. Go for the seafood and stay for the Key Lime Pie which far outshines any other in the Keys. Little wonder that Mark has also parlayed his seafood offerings into a very successful online seafood shipping company, www.keywestseafood.

6. The Best Stay-Overs

Forget designer-name hotels, go for historic character and comfort. Simonton Court, which once housed the workers and operations of a 19th century cigar factory, is a lushly landscaped haven from busy Duval Street. Another winner is The Marquesa, a superbly appointed boutique hotel that’s on the National Register of Historic Places. Heron House is also a must-see, if only for its hand grown rare orchids.

7. Pelicans

You’ll find them congregating where-ever there’s the prospect of another fishy meal which in the Keys in virtually off every shore and boat dock. Feed them some morsels, watch them scrap, but keep them at a good wing’s length. These birds have enough attitude to rival a New York cabbie.

8. Hemingway House

Fan or not, this wonderful mansion is peppered with Hemingway eccentricities, not least of which is a drinking fountain made out of a urinal and the home’s famous six-toed cats. There’s 31 polydactals of the 61 resident felines, all of which are named after famous folks such as Charlie Chaplan, Ava Gardener, and Edgar Allen Poe. Did any tell Liz Taylor she’s actually in the cat cemetery? Incidentally, Hemingway’s boat, Pilar, is at World Wide Sports at Islamorada.

9. Scooters

Parking is a tight commodity around Key West’s busy and narrow streets which is why folks zip around on mopeds and scootcars. Believe it or not, a great place to rent the former is at the Moped Hospital. The latter can get a bit pricey but are heaven sent if it rains.

10. Bones & Bullies

Nicknamed the “gray ghosts of the flats”, bone fish put up a warp-speed chase that will challenge the best of anglers, provided a bully doesn’t get into the fight. Four and five foot long barracudas are hook savvy predators but the promise of their explosive sky-dives and cartwheeling jumps are a lure that will convert wannabes into sports-fishing enthusiasts.

Words for the road

First stop towards Key West should be Alabama Jacks on the “old road” to the Keys. It’s a bit off the beaten track but a favourite haunt of Harley riders and those in the know. It looks rough and ready from the outside, but dishes up the best conch fritters in the Keys. Second stop should be breakfast at Robbies, a tiny 1950’s style diner at Islamorado, where man-size pancakes, bacon and eggs are served alongside the opportunity to hand-feed some pretty feisty (finger-grabbing) tarpon. Marker 88 nearby is a good option for dinner and patio cocktails. Take the time to detour through Pine Key; the thigh-high Key deer are a delight to find and unexpectedly tame. And if you want to experience how the other half lives, take a boat across the flats to Little Palm Island, at upscale resort off Little Torch Key where thatched-roofed cabanas house guest rooms, restaurants and an exotic outdoor spa.

Photo credit:

Header Image by Pixoman from Pixabay

Mallory Square sunset celebration images by Sridhar Saraf under CC 2.0 license

Pelicans at Robbies by Ed Schipul under CC 2.0 license