With Key West’s proximity to Cuba, it should come as no surprise that cafe con leche, the heady mix of espresso shots and piping hot milk hand-whipped into a froth, and its phalanx of accompaniments — buttery, crispy Cuban toast, thick Cuban sandwiches bursting with fatty ham, fried pork and more — have become as deeply woven into the fabric of the area as Duval Street’s ubiquitous drag queens. And the establishments that serve these brews are often colorful hives in which one can sneak a peek at the daily rhythms of local life. So, on a return visit to Key West last year, I decided to visit some old favorites.

Five Brothers

Ask any local where to get coffee, and most of the time, two words will emerge: Five Brothers. This cozy corner coffee shop and grocery on Southard and Grinnell Streets has been a local grocer for more than 70 years. But in 1978, a Cuban immigrant named Heriberto Paez took it over, adding Cuban coffee and snacks to the lineup.

If you want to take the pulse of Key West, head to Five Brothers just after 7 a.m. on any given day. The well-heeled, the artists, the blue-collar workers all congregate here, wedged among the tall shelves stocked with everything from wine to cereal, and patiently wait in line, gabbing with one another as Pepe Paez, who took over the business from his father in 1996, swiftly and silently whips up little cups of coffee.

“I see the same people here every day and wish them a great day at work,” said Debra Butler, owner of Debra Butler Design Studio, an interior design firm a few blocks away. In fact, Five Brothers is such a Key West staple that during the rare occasions each year that Mr. Paez closes the shop to take his family on vacation, “people will still meet in front,” Ms. Butler said. “They’ll bring their own coffee and talk about their day.”