Jay was dressed head to toe in black, sporting a frayed Abe Lincoln goatee and standing around 6½ feet from his steel-capped boots to the rim of his tall top hat. Our ghost host had one simple rule for our after-dark tour of Key West’s most haunted spots – if anyone so much as whispered ‘boo’ in our direction, we were to cast a loud, collective ‘You’re Doomed!’ at them.
We really had walked into a nightmare.
Still, the locals seemed to get just as much of a kick out of this nightly show as the visitors, and we soon found our corny groove, ‘dooming’ just about everyone in town over the next two hours.
Jay proved to be one of many colourful characters that populate the tiny little sun-and-sand mecca of Key West, the southernmost point of the continental US, just a stone’s throw from Cuba and ‘Home of the Sunset’.
It’d been a journey just getting here – a 180-kilometre jaunt along the impressive Overseas Highway, a long road with 42 bridges linking dozens of tiny islands. As road trips go, driving out to sea is up there.
But back to Jay. Despite his dramatic storytelling, or perhaps because of it, our ghost hunt turned up nada, although we did head back to the Chameleon theatre the next night to tap on the glass and whisper ghostly summonses. No joy. Where’s Oda Mae Brown when you need her?
Waiting for signs at the spooky Artist House and the haunted Chameleon theatre.
It was on to ghosts of the literary past the next day in the ancestral polydactyl cats and stories of charming Hemingway House, home to legendary author Ernest Hemingway in the 1930s.
Here Drake, another quirky Keys guide who looked remarkably like Jay only shorter, regaled us with tales of the legendary tiffs between Hemingway and his extravagant second wife Pauline. We lingered over the period furniture and gardens here, paying special due to the in-ground pool, the first of its kind in Key West and a steal at what would be around $330,000 dollars today. You’d want a cold splash after spending that.
We followed up six-toed cats with exotic birds and butterflies at the peaceful Key West Butterfly and Nature Conservatory, a great place for communing with winged creatures and practising your macro photography.
Of course, a trip to the ‘Home of the Sunset’ wouldn’t be a fait accompli without some kind of sunset homage, which is why our last afternoon found us on a party boat downing plastic cups of bucket-made Margarita and beer to the tunes of a Beach Boys cover band well past their prime.
Several hours later we teetered back onto dry land and into the thronging mayhem of Duval Street, locally known as ‘Hysterical Street’ to counter ‘Historical Street’ one block over.
The name is apt: 200-odd bars duel it out nightly with live music while scantily clad girls and raucous guys spill out into the street with giant plastic tubes of Daiquiri. If American films are anything to go by, we were smack in the middle of one massive college street party. It was loud, crowded and surprisingly good fun!
And just like that, our 48-hour taste test of Key West was up, but as two more laid-back travellers, we’d had more than our fill of quirk and party. We left the keys and settled in for the magic highway back to Miami.
Good to know
Key West is the southernmost city in the US and a 3½ hour drive from Miami. As road trips go, the Overseas Highway is considered one of the greats.
There are plenty of places to stop and stay along the drive, from bigger towns like Key Largo to smaller villages like Islamorada.
We visited Key West in April and while it was still busy, March to April is apparently the best time to go as the crowds are smaller, hotel prices come down but days are clear and in the mid to high 20s (high 70s to mid 80s Fahrenheit).