Rediscovering A Colorful Community On The Bay

by Curt Kovener

Gulfport, Florida is an open, welcoming, age and culturally diverse ‘Old Florida’ community on Boca Ciega Bay nestled between St. Petersburg and Clearwater. We learned about it in early 2018 after hearing it had a ‘Key West vibe and a Costco price’. We stayed; we liked.
After a flight to Tampa, we returned to the colorful little city by the bay on Christmas Eve and spent a restful and exercise filled two weeks.
Chuck and Karen Colley were our hosts at Gulfport Beach Cottage. Fans of John Mellencamp will be pleased to know that their 1925 vintage ‘little pink house’ fits right in with all of the other colorful community locations.
Looking out the front window of our second story quarters we can see the sailboats and yachts on Boca Ciega Bay, some always active beach volleyball courts, and The Tiki Hut Bar & Grill is only 23 steps across the street from where we stayed. A stroll down Shore Blvd, will bring you to The Neptune Grill, then Caddys, followed by Salty’s Gulfport Bar and finally O’Maddy’s Bar & Grille. All have music every night and all are within a two block crawl of where we stay. All offer indoor and outdoor drinking/dining and a relaxing view of the bay off the Gulf of Mexico.
Walk north in the middle of the two block strip onto Beach Blvd. for more restaurants. Stella’s (THE place for breakfast), along with Tangelo’s, Fortunato’s, Backfin Blue Cafe, Isabelle’s in the Historic Peninsula Inn for classic southern cuisine along with coffee bars, and artsy boutiques are within three blocks of the bay.
Gulfport got its name in the 1800’s when the area was palmetto scrub and tidal flats. A road was cleared (Beach Blvd.) to allow residents, businesspeople, and fishermen access to the bay to take a ferry across through the inland isles to the Gulf of Mexico, thus the city’s name: Gulfport.
We ate at different places (none of which were franchises) nearly every day and never had a bad meal.
Pia’s Trattoria, a wonderful Italian restaurant on Beach Blvd., deserves a second or third visit…but then we might have missed Crabby Bills in St. Pete Beach, Ted Peters Smoked Fish in South Pasadena or Central Ave. Brew & BBQ in St. Petersburg.
Gulfport is very walkable which is good, otherwise Becky & I would have returned from our vacation 10 pounds heavier.
We enjoyed looking at the eclectic homes, some with well manicured lawns and some looking like an overgrown jungle. Nearly wherever we went, little brown geckos and skinks scurried about. On the east side of the community, Clam Bayou offered a peaceful stroll over crush seashell paths and wooden bridges in a grotto offering refuge to manatees (which, unfortunately, we did not see). But we did see Osprey on the nest, brown pelicans fishing and white egrets dining on those brown geckos.
Having none in this area, we learn a lot about the value of public transportation. Bus 23 quickly became our favorite tour bus into St. Petersburg and the city’s art and museums along Central Avenue. And it was only $1.10 to ride.
A 40-minute trip to Myakka State Park provided views of some large alligators from the safety of our tour boat.
Times Square has nothing over Salty’s Bar in Gulfport on New Year’s Eve as we and about a thousand close friends awaited the colorful grouper to drop heralding in the new year.
And except for New Year’s Eve, all the bars and their music close at 11 p.m. each evening. And we are grateful for the quiet night sleep with our windows open in December and January.
On our last afternoon in the eclectic community, we took our umpteenth stroll on the Williams Pier where we saw what made our southern trip complete: dolphins swimming in the bay.
If you’d like more information about this little know community close to everything long on to: or