26 miles S of Palm Beach, 40 miles N of Miami, 21 miles N of Fort Lauderdale

Boca Raton is a well-manicured, but mostly soulless suburban city, home to ladies who lunch, country clubbers, and retirees. The city’s name is often mistranslated as “rat’s mouth,” but the phrase is actually a nautical term meaning rocky or jagged inlet. The original settlers were the people of the Glades Culture, who lived here for a thousand years before being driven out in the 1800’s by pineapple farmers and land speculators, the latter drawn there by the development of the intracoastal waterway, and the railroad. Today the greater Boca Raton area is home to some 250,000 people.

If you’re looking for funky, wacky, and eclectic, look elsewhere. Boca is a resort community that, though it has come a long way from Seinfeld’s Del Boca Vista visions of old people and HOAs, is still pretty boring. With minimal nightlife, entertainment in Boca is restricted to leisure sports, good dining, and upscale shopping. Its 2-mile stretch of beach is well maintained and crowded, though never mobbed.

Delray Beach, named after a suburb of Detroit, is a sleepy-yet-starting-to-awaken beachfront community. Its bustling, buzzy downtown area includes Atlantic Avenue, which is known for restaurants, quaint shops, and art galleries. Delray’s bars and restaurants make for a lively scene after nightfall especially, and lodging costs are lower here than in Boca Raton. Because of their proximity, Boca and Delray can easily be explored together. Still, compared to Boca, Delray is much more laid-back; it’s trendy, but hardly as chichi, and definitely a cuter little beach town than sprawling, suburban Boca.