The chances are that unless you’re from Pinellas County or spent some time in St Pete, you probably don’t know about the little town of Gulfport.
No, not that one in Mississippi. The funky, eclectic, progressive, and sometimes weird town tucked in between St Petersburg and the Boca Ciega Bay.
If you’ve been following our blog for any time, you might recognize the name from our post on the city’s Clymer Park Art Walk.

The History of Gulfport
Gulfport has been known by several names over the years. Initially, it was named “Disston City” after Hamilton Disston, who purchased the land in 1884. But, it seems the U.S. States Postal Service would not accept that name because it conflicted with the name of a town across the bay in Hillsborough County. So, it was changed to Bonifacio. Then in 1890, the name was changed to Veteran City. And in 1910, the name officially changed to Gulfport.
Gulfport’s Eclectic and Weird
Yes, Gulfport is eclectic and weird, but in a wonderful way.
It tends to be pretty progressive and, over the years, has attracted lots of artists and is amazingly LGBTQ-friendly. There are no chain stores and no meter parking.


But, what it does have is an excellent mix of fun. Gulfport has an incredible First Friday Art Walk that attracts lots of artists from across the region. It also has a Third Saturday Indie Faire and a Tuesday Fresh Market.
Gulfport is also known for its quirky GeckoFest, a family-friendly celebration of the end of summer.
Beyond those, it has an incredible local theater, an LGBTQ Film Series, Toddler Storytime, and even ballroom dance lessons at the historic Gulfport Casino.
No, Not That Kind of Casino
The Gulfport Casino actually has nothing to do with gambling, and it never has. The name casino was taken from the Italian ‘casa’ for home and referred to a public gathering place.

From what we know, the original building fell in 1921 during a hurricane, with the second coming down in the early 1930s. The current building was erected in 1935 with a dedication and gathering of nearly 1,200 people.
It acted as a gathering place for locals and visitors, a trolley stop, and you could take a ferry across the water to Pass-a-grille.
Beaches, Boating, and Fishing
Sitting on the Boca Ciega Bay, Gulfport has calm waters, and white sand beached. The waterfront has a beautiful fishing pier and picnic areas, kids’ areas, a skate park, a community center, and about a half dozen beach volleyball courts.




On the edge of town is a marina and easy access to Tampa Bay and the Gulf of Mexico.

The Waterfront District
The Waterfront District is our local go-to place for an evening stroll and dinner. There are local galleries and boutiques and some fantastic local food.

Recently, Gulfport got GulfPerk Coffee Bar, an excellent coffee shop in a 1930s bungalow. And, right down the street is the Gulfport Brewery – someplace we’re anxious to check out.
The street is dotted with 1930s bungalows and historic buildings. Some of which are private homes, and others have been converted into businesses.



The local Welcome Center is actually located in what looks to be a mid-century motel.

Farther up the street is the Historic Peninsula Inn which has been part of Gulfport since 1905. Originally known as the Bay View Hotel, it became a veteran’s hospital during WW II, a nursing home in the 80s, and was abandoned and almost demolished. Thankfully it was rescued, renovated, and reopened in 2002.

Dinner and Drinks in Gulfport
Gulfport has some great options for dining. A few of our favorites are:
O’Maddy’s
An excellent waterfront place with an eclectic menu, outdoor seating, and live music. We know we’ve used the term eclectic several times, but there is no other way to describe their menu. We’ve never had a bad meal there and always try to get something different.
Their Lobster BLT is ridiculous with big chunks of lobster meat. Be sure to check out a regional favorite, Fish Spread.

Fish Spread is a local phenomenon. You smoke oily fish like mullet or amberjack and mix it with celery, onions, and mayo. You’ll find them served with saltines or club crackers, veggies, and a spicy jalapeno topping.

Fish Spread was reportedly started by a local, Ted Peters, back in the late 1940s. But the story and their iconic smokehouse and drive-in restaurant are a story for another blog post.
Caddy’s
A relative newcomer to the Gulfport Waterfront, but not the area, with several restaurants up and down the local coast. Great food and drinks, a second-story deck with fantastic views, live music, and we’ve walked by some nights when they were hosting Drag Bingo.

Neptune Grill
Neptune Grill is a family-owned restaurant serving Greek and Mediterranean food. They have indoor (air-conditioned) and outdoor dining and live music and have recently added a walkup take-out window.
Stella’s
This fun place is a go-to for breakfast, brunch, or lunch. Names for the owner’s late aunt Stella, who devoted her life to the church as a nun. It’s all about family and good food.
They’ve recently moved up the block from their former location, offering more space and lots of outdoor seating.

Seriously, you can’t miss with anything on their menu! It’s Mark’s go-to when he wasn’t an amazing Rueben Sandwich.
After nearly four years in St Petersburg and living just up the street, we always find something new and fun in Gulfport. Be sure to check it out. You’ll be glad you did.
The mailboxes are so innovative. Loved them. I am not a casino man, but would love to picnic there someday. Thank you so much.
You’ll love Gulfport and Saint Petersburg! BTW, the ‘casino’ actually has nothing to do with gambling – it’s a beautiful dance hall, event venue and gathering place!