Gulfport

Between the view of Tierra Verde across the bay, the artsy and quirky shops, fabulous waterfront restaurants and thriving art scene, Gulfport is a funky community all its own.

Gulfport is known for GeckoFest, an annual celebration of the end of summer. This isn’t a typical small-town street festival—it’s a circus-like event with offbeat street performers, people dressed in crazy costumes, groovy music and everyone just having a grand ole time in true Florida fashion. If you don’t make it to GeckoFest, you should definitely get to one of Gulfport’s other events such as the Art Walks, which take place on the first Friday and third Saturday of every month, or the farmers market every Tuesday.

Nightlife here is casual and laid back. Take a seat at a barstool at any of the waterfront bars like Salts Gulfport or head to Beach Boulevard for a string of art shops, restaurants and bars. Head on over to Little Tommies Tiki for a fun Key West-themed spot with craft beers and live music performances most days of the week.