For the last few years, I’ve been strangely gripped with an urge to see the southernmost part of the U.S., Key West, Florida.

I must have read that Key West is overrun by friendly cats and chickens….and well, we love us some cats and chickens.  Or, it could have been the Key Lime Pie.

Mmm…pie.

What landed us in Key West, and in Florida in general, was a process of elimination.  Having committed to a late December family wedding in D.C., where winter temperatures often hover around 20 degrees, we began to toy with East Coast-adjacent escapes to the sun.

With only six days to play with during Christmas week, the Caribbean was laughably exorbitant and flights to our dream trips in Central America proved too complex and time-consuming.  So then there was Florida, dangling before us like a coconut on a palm tree.

Our direct flight to Miami from Dulles was just over two hours long, though the drive to Key West was three-and-a-half more. Flying into Ft. Lauderdale would have been cheaper, but would have added another 45 minutes’ drive time.  Flying into Key West would have been both more expensive and required a change of planes.  Miami seemed a good compromise, and considering the gorgeous drive down, it was.

The greatest advantage of taking a tropical vacation in our own country was the feeling that time could expand. Assured by the relative proximity of Florida, we felt content to spend whole hours in the pursuit of little.

View from Simonton Court's Camellia Room

Our historic B & B, the Simonton Court, was the perfect spot to get on Key West’s laid-back wavelength.  I’d booked us the Camellia Room, with a big second-story balcony overlooking a lush garden of silvery palms and a gently heated pool.  One quiet afternoon, we found we had the whole property to ourselves, and swam, sunned, stretched, and read.

You know, like vacation.

While the Simonton staff couldn’t have been more helpful or friendly, their Achilles heel is their tragic coffee.  (Listen, you can’t have everything.)  For a better brew, we ventured to the Coffee & Tea House of Key West (1218 Duval Street), where a rich cappuccino comes with a little snark from the quirky proprietress (who, despite her attempts to convince you otherwise, clearly likes human beings).

Once caffeinated, we just took to wandering.  Key West only seems to be about 20 blocks long in any direction, so you can either rent a bike or, like us, walk almost everywhere.  We mostly left our car parked on the streets, since Key West holiday tradition dictates free parking for a few days before and after Christmas.

Cat at the Ernest Hemingway House

We took the money we saved and shelled out $12 bucks apiece to visit The Ernest Hemingway Home.  A modest 1850s house set amidst a lush tropical garden, it’s prowled by about 60 six-toed cats who’ve come to expect the constant adoration of strangers.  Check out the gorgeous ceramic tile everywhere and the terrible living room artwork donated by decades’ worth of Hemingway’s fans.  Our favorite was an oil portrait of the house with two cats in the extreme foreground; the felines and home appear to be exactly the same size.

We snaked in and out of the gently run-down streets of the Bahama Village neighborhood, where every single person, often sitting on lawn chairs on their scrabbly front lawns, smiled and said hello to us.  Seabirds clustered on electric wires overhead, chickens scratched the dirt and hopped fences, and weary clapboard houses were sometimes spruced with pink, blue and orange paint.  In a sad sign of the times, the entire site of the outdoor flea market here is currently for sale.

We strolled as much of boorish, kitschy Duval Street as we could stand.  Amongst the weaving drunks, there are occasional bright spots, like the salads at the big ol’ Victorian The Grand Cafe and the pastries at Croissants de France.  However, the closer you get to the north end of Old Town, the more Duval devolves into day crowds pouring off docked cruise ships, sad and shabby bars, and offensive t-shirt shops.

A t-shirt that has about thirty expletives followed by a cheery “Key West” at the bottom seems a bizarre ad for a sleepy little place on the water, but then…no one asked us what we think.

True Key West culture is actually a mix of flashy drag revues, country club refugees in golf shirts and Bermuda shorts, quiet and church-going folk, bemused European expats, and aging, nicotine-stained drunks weaving along the streets in broad daylight.  Eclectic, yes, but somehow there’s room on this small island for everyone.

From L: Bahama Village; just off Duvall Street; house on Poorhouse Lane

In particular, Key West attracts middle-aged gay men looking to escape the big city for a quieter life.

One such man, David Case, abandoned a career at the famous New York City teahouse chain, Sarabeth’s, only to start Sarabeth’s Key West (530 Simonton Street) in a vibrantly-painted Victorian-era synagogue; he now happily greets his patrons in outfits that would make the writers of The Official Preppy Handbook weep with joy.  They do a beautiful breakfast here, but skip the dry potatoes in favor of their fresh-baked muffins.

Much of the gay community lingers on the elegant patio at Square One (1075 Duval Street) to smoke, drink, and indulge in the best (house-made) Key Lime Pie we had on the whole trip.  While you’re there, try not to miss the roasted garlic with feta and dill, either.

Hmmm.  I think I’m beginning to piece together how we both gained five pounds on this trip…

One afternoon, we stumbled upon the Key West AIDS Memorial, an austere concrete bridge leading out into the choppy teal sea, and read just some of the hundreds of names of inscribed on its path.  With tears in my eyes, Adam gallantly steered me next door, past the also heartbreaking African Cemetery, where almost 300 of the last intended slaves, sick from their forced journey, were buried by Key West locals in 1860.

The cemetery’s beach park sits adjacent to the slightly shabby but altogether charming Key West Garden Club. After oohing over their sparkly, shell-strewn Christmas tree, we plunked ourselves down at a tiled table beside the ocean and listened to a salty breeze shiver the palms.

Christmas tree at the Key West Garden Club...and Sea Sponge Man

We beat the tourist rush at downtown Mallory Square by poking around before 10am. Any later, and the monstrous cruise ships unleash their human cargo upon countless souvenir shops, bars, and a pirate museum.  In the morning quiet, we saw skinheads getting tattoos, a few well-fed chickens, an old-timey conch fritter stand, a tinsel-trimmed Christmas tour train, a few stalwart red-brick municipal buildings masquerading as castles, and our favorite — Sea Sponge Man.

Later that evening, we booked a two-hour sunset sailboat ride through Floridays and sailed past the Square again, where hundreds of revelers gathered for the nightly tourist ritual of greeting the sunset.  Ruffled by the cool sea air, we were sometimes kept company by the friendly female first mate, a young Venezualan woman who’d three years earlier followed her love from San Francisco to Key West.

She told us a few things about the island:

Fancy people steer their yachts from all over the world to dock in Key West free of charge and rules.  Sure, this practice has all but killed the lovely coral reefs that used to hug the coast, but now we all get to ogle the shiny boats instead.

If you’re hell-bent on the perfect Key West sunset, visit in late May or early September.

Right beside swanky, private Sunset Key Island, there’s a scrubby, uninhabited isle, home only to a few transients. The former owner, a grande dame of Key West society, died not long ago, stipulating that the island be kept safe from development; her grown children, left behind in an encroaching recession, apparently now have other ideas.  Might not make a great resort, but perhaps a good soap opera.

Travels With Two