Gulfport is the small town inside the county
An arts community on Boca Ciega Bay with a walkable waterfront main street, a monthly art walk and a casino building that is actually a ballroom.

Gulfport is a small city on Boca Ciega Bay, wedged between St. Petersburg and the barrier islands, and it has kept a character that most of the surrounding county traded away. Beach Boulevard runs down to the water past galleries, restaurants and independent shops, and it ends at a small beach and a fishing pier.
The Casino is not a casino
The Gulfport Casino, the prominent waterfront building at the foot of Beach Boulevard, is a historic ballroom and event hall. The name is left over from an era when "casino" meant a social gathering place rather than gambling. It has hosted dances for generations, and ballroom dancing still happens there regularly.
Art walks and markets
Gulfport runs a regular art walk in the evening along Beach Boulevard, with galleries open and vendors set up, and a weekly outdoor market during the cooler part of the year. Both are the kind of event where the residents outnumber the visitors, which is what makes them worth attending.
The water side
Boca Ciega Bay is calm, shallow and protected, which suits kayaking and paddleboarding better than the open Gulf does. The municipal marina and the beach both look west, so sunsets over the water are the daily event.
Across the water is the Clam Bayou Nature Preserve, a restored estuary shared with St. Petersburg, with trails and paddling access.
Why it feels different
Gulfport is physically small, it has its own city government, and it decided some time ago what it wanted to be. There are no high rises on the waterfront. The result is a place where a main street still functions as a main street, which in Pinellas County is rarer than it should be.
Cover photo: Uptownnow / Wikimedia Commons (CC BY-SA 3.0). Source.
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