Why Gulfport Is Pinellas' Most Charming Little Town
Local Guides

Why Gulfport Is Pinellas' Most Charming Little Town

The Pinellas Podcast TeamJune 2, 2026 6 min read

Artsy, walkable, and delightfully weird — Gulfport is the waterfront village that locals hope stays a secret.

Tucked along Boca Ciega Bay, Gulfport is a small waterfront town with a big personality. Independent shops, a beloved casino ballroom, art galleries, and a genuinely bohemian spirit make it one of the most charming corners of Pinellas County.

Beach Boulevard

The heart of Gulfport is Beach Boulevard, a walkable strip of local restaurants, galleries, and quirky boutiques. There are no big chains here — just independent businesses with real character. Come hungry and plan to browse.

The waterfront and Casino ballroom

The Gulfport Casino isn't a gambling hall — it's a historic waterfront ballroom famous for its dances, from swing to Argentine tango. The adjacent beach and fishing pier are perfect for a slow afternoon.

Markets and art walks

Gulfport hosts a lively Tuesday fresh market and regular art walks that fill Beach Boulevard with vendors, live music, and local makers. Check the town calendar and time your visit to catch one.

Make a day of it

  • Start with brunch on Beach Boulevard
  • Browse the galleries and vintage shops
  • Watch the sunset over Boca Ciega Bay
  • Stay for live music at a local haunt

Gulfport proves you don't need a big beach to have a great beach town. Go see for yourself.

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