• Key West's Kermit Carpenter awaits visitors to his shop with a fabulous Key lime pie.


  • By: Steve Smith
  • September 16, 2015

It’s already the middle of September and Key West is still hopping with parties and events. Our Labor Day holiday and Womenfest have passed, and around Sept. 17 we roll out the pavement for the 43rd annual Poker Run.

Every day, locals flock to 5 Brothers for Cuban sandwiches, cafe con leche and other treats. (Photo courtesy of 5 Brothers)

Every day, Key West locals flock to 5 Brothers for Cuban sandwiches, cafe con leche and other treats. (Photo courtesy of 5 Brothers)

Estimates predict between 10,000 and 14,000 bikers will participate in this annual fundraising event. The idea is to ride your Harley (or the equivalent) down and through the chain of islands we call the Florida Keys. During the “run,” riders have time to snorkel, swim and sightsee as they traverse the Overseas Highway that stretches some 125 miles and crosses 42 bridges.

Check out the thousands of incredible “bikes” that will be parked on lower Duval Street this weekend. Poker hand winners compete for cash or a new Harley; the fun is spending time on Duval looking at and photographing bikes more unique than any you’ve ever seen before.

As you wander through Old Town Key West, explore some quaint cafés tucked around the neighborhoods. On the corner of Southard and Grinnell streets is 5 Brothers Grocery & Sandwich Shop operated by the Paez family. In 1996, Pepe Paez took control of the espresso machine from his father Heriberto. Like a symphony conductor, Pepe orchestrates cups of creamy sweet café con leche and the famous strong sweet Bucci — a tiny cup of rich, almost-black espresso and sugar. Add a Cuban bread cheese toast, and your morning treat is complete.

Cuban Coffee Queen Key West

Key West’s popular Cuban Coffee Queen serves eager customers in the Historic Seaport. (Photo courtesy of Cuban Coffee Queen)

Other Paez family specialties include a great Cuban Mix sandwich and my favorite, the Medianoche (which means “midnight” in Spanish). So named because it was served in Havana nightclubs after midnight, the sandwich includes layers of ham, salami, fresh Cuban pork, swiss cheese and pickles stacked on sweet egg dough bread and toasted in a press.

A few blocks away in the Historic Seaport is the Cuban Coffee Queen. This tiny oasis next to Mac’s Sea Garden serves iced café con leche and huge Cuban sandwiches to enjoy as you stroll along the harbor. Recently the Queen opened a second location off Duval Street in Key Lime Square, adjacent to the Southard Street intersection.

Key West Kermit Key lime pie

Kermit awaits visitors to his shop with a fabulous Key lime pie. (Photo courtesy of Kermit’s Key West Key Lime Shoppe)

Across the road from the Seaport, at the corner of Elizabeth and Greene streets, you’ll find Kermit Carpenter’s Key West Key Lime Shoppe and Kermit’s Kitchen Café. Known around the world for his famous Key lime pie, Kermit opened his café to serve breakfast, lunch and light fare. The menu offerings are prepared using Kermit’s own marinades and sauces (available to take home from his shop) and can be packaged to take to the beach or on a water adventure.

Take a short trip down Simonton Street to discover Deuce’s “Off The Hook” Grill, an intimate bistro-style seafood grill on the corner of Petronia Street. Rated 4.5 stars by TripAdvisor, this café serves fresh seafood, plus Greek and American dishes. A favorite is their Gobbler, consisting of freshly roasted turkey uniquely served over bacon “smashed” potatoes on a sage–stuffed waffle. Reservations are recommended since the cozy eatery only has six tables and six counter seats.

Taste your way around Key West, where you’ll find world-class food in the most remarkable places — and have a great trip to the island we locals call paradise.

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