historic house Key West
  • Quintessential Key West pleasures include strolling the Old Town streets past pastel-painted homes adorned with flowers.

     

  • By: Carol Shaughnessy
  • November 20, 2019

My brother-in-law is a sophisticated New Yorker. He lives in a spacious, elegant apartment not far from Central Park, and escapes on summer weekends to a sprawling Victorian home on Long Island. He’s the kind of guy who looks genuinely comfortable in a designer three-piece suit.

Cuban bread might be enjoyed plain with butter, or stuffed with meat and cheese in a yummy sandwich like this one from Key West’s landmark El Siboney Restaurant.

So why did he transport half a loaf of (carefully concealed) Cuban bread through the Miami airport?

Simple. My brother-in-law, like so many people who visit Key West, fell in love a while back with the sights, colors and flavors of the island — particularly the crisp, floury taste of fresh Cuban bread. When he leaves after a visit, his leftover loaves leave with him, to be enjoyed in the metropolitan sprawl of Manhattan.

And what tops this urban sophisticate’s wish list every year as the holiday season draws near?

Cuban bread from his favorite Key West bakery in a cardboard mailing tube.

While fresh Cuban bread wouldn’t delight the heart of every visitor, purchasing and packing it (by some strange coincidence, a loaf fits perfectly in a standard mailing tube) reminded me of treats we Key Westers can enjoy every day — but that aren’t easily experienced in other places.

For example, there’s the old-time pre-sunset tradition of taking the pooch to play “coconut fetch” at Dog Beach. Tucked into the corner of a mostly residential neighborhood at Waddell and Alberta streets, this tiny beach fronting on the Atlantic is a favorite of locals and their dogs.

The Afterdeck Bar at Louie’s Backyard is a great place to sip cocktails and watch pooches play at the adjacent Dog Beach.

Just before sunset, it’s not unusual to see 10 or 12 canines playing with frisbees, coconuts, or each other in the shallow water — while their human companions watch from the beach or the water’s-edge cocktail deck at Louie’s Backyard, the popular gourmet restaurant next door. (Yes, Key West has a great dog park, but some longtime residents still prefer Dog Beach.)

FYI, sipping late-afternoon cocktails at Louie’s waterfront bar is also a quintessential Key West pleasure. Located in a pastel house once owned by a shipwreck salvage captain, Louie’s opened as a restaurant in 1971 with one waiter, a cigar box cash register, and seating for 12.

It quickly became famous for its cuisine, relaxed atmosphere and well-known patrons — including entertainer/author Jimmy Buffett, novelist Tom McGuane and Ten Speed, a legendary mutt who drank Kahlua and cream at the outdoor Afterdeck Bar.

These days, the bar still attracts regulars ranging from local treasure hunters and fishing guides to literary luminaries and celebrities hoping to remain incognito.

After dark, lights spill out from the restaurant to illuminate the bar area, the stars above look practically close enough to touch, and the Atlantic unrolls seemingly halfway to Cuba.

Hogfish Bar Florida Keys

It’s technically just outside Key West, but savoring seafood at the waterfront Hogfish is a treat for savvy island residents and visitors.

Whether after dark or during the day, another of my favorite pastimes is taking a leisurely stroll past historic homes in the Old Town district. Key West has what’s believed to be the U.S.’s largest predominantly wooden historic district, containing almost 3,000 structures — many dating from the 19th century.

There you’ll see lovingly restored Victorian frame houses with wraparound verandahs next to heart-meltingly gorgeous pastel cottages. Luxuriant vegetation is everywhere, thriving in the year-round subtropical temperatures: royal poinciana trees flaunting flame-colored blossoms, hibiscus blooms cascading over white picket fences, tall palms, the red bark of the “tourist tree” peeling like the overexposed legs of sun-hungry visitors.

And speaking of “hungry,” a trip to the Hogfish Bar & Grill also heads my list of only-in-Key-West treats (though actually, this hard-to-find hideaway stands just outside Key West on neighboring Stock Island).

Most diners at the funky locals’ watering hole sit outdoors at weathered picnic tables, overlooking picturesque houseboats and sailboats moored at the adjacent dock.

The restaurant’s signature dish is hogfish, a diver–caught fish with a light flavorful taste, but all kinds of fresh Florida Keys seafood is served (including a smoked-fish dip that may be the best in the known universe).

Another time, I’ll share more of my favorite Key West experiences — but right now, I’m off to pick up a loaf of Cuban bread and a mailing tube.

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