Delray Beach may have humble origins, but its evolution into one of Florida’s most vibrant coastal communities feels almost inevitable. Incorporated in 1911 with just 250 residents and a bustling pineapple industry, the town began as a quiet stop along the Florida East Coast Railroad. By 1927, the addition of “Beach” to its name marked the city’s expansion eastward to the Atlantic, setting the stage for its future as a lively seaside destination.
Today, Delray Beach counts more than 64,000 residents and draws visitors from across the country—especially boaters and snowbirds who appreciate its waterfront lifestyle. The Intracoastal Waterway physically divides the city into two distinct areas, downtown and the beach, but both pulse with a shared energy shaped by the rhythm of the drawbridge. Traffic pauses each hour as the bridge lifts, a reminder that life here revolves around the water.
The beachfront remains one of Delray’s treasures. Umbrellas and wooden chaises line a carefully maintained shoreline bordered by natural sand dunes and coastal vegetation. It’s a postcard-perfect setting, but the downtown district is what truly fuels Delray’s reputation. Atlantic Avenue is lined with eclectic boutiques, from Snappy Turtle to Periwinkle, keeping fashion lovers busy throughout the day. After sundown, restaurants and bars come alive. Favorites include Blue Anchor for live jazz and classic rock, and Boston’s on the Beach for its well-known reggae nights.
The Pineapple Grove Arts District adds another layer of personality with its Artists Alley, where more than two dozen creators open their studios each month for public strolls and conversations.
Boaters will find excellent docking options at both The Yacht Club at Delray Beach—ideal for vessels up to 130 feet—and the Delray Beach Municipal Marina, though transient slips there fill quickly.
Great dining is easy to come by, with local staples like Caffe Luna Rosa, Deck 84, and The Grove offering everything from waterfront views to elevated cuisine.
What began as a small agricultural town has become a lively, artsy, beach-loving community—a place fully deserving of its title as America’s most fun small town.
Harlan Kilstein the publisher of this website is a resident of Delray. He has lived in Palm Beach County since 1997, In that time he has explored everything for surfing on private beaches in Delray to walks up and down Atlantic Avenue.
He is known to drop everything at a moment's notice to fish in Delray Lakes, bird watch, goes horseback riding or play pinball at the Delray Pin Ball Museum.
You can find him either sipping a coffee on Atlantic Avenue or drinking a flight of whiskey at Warren's.
One thing is certain, he knows Delray Beach.
