If you have lived in Gulfport for more than a couple of years, you already know the map by heart. Beach Boulevard runs down to the pier, the Casino anchors the waterfront, the tuesday market fills the street, and 49th Street South has always been the quieter industrial-adjacent stretch where the tile shop and the auto place sit next to a few longtime holdouts. That mental map is quietly getting redrawn this summer, and the shift is worth paying attention to before the Labor Day weekend crowds arrive.
The short version: Beach Boulevard is filling back in with independent openings after the 2024 hurricane turnover, and 49th Street South is picking up a second wave of small businesses that would have looked out of place there three years ago. It is not one big story. It is a cluster of very small ones that, taken together, mean the streets you walk on a Saturday morning look different than they did last summer.
Beach Boulevard is still turning over from the storms
The clearest example sits at 3129 Beach Boulevard, in the space that used to be Paw Paw's pet supply store. Paw Paw's closed in late 2024 after back-to-back hurricanes, and the storefront sat empty for months. It reopened on May 23 as Drift + Story, a boutique specializing in coastal-inspired apparel, accessories, and locally made goods, run by owner Haley Santamaria. If you have not stopped in yet, the inventory leans toward women's apparel, sunglasses, hats, swimwear, candles, and children's beach accessories, with more men's and kids' merchandise on the way as the shop grows into the space.
Santamaria's own explanation for why she opened when she did is the sentence I keep returning to when I think about this summer on Beach Boulevard. "Over the course of the past year, we've been able to see everything in Gulfport kind of bounce back, with new businesses opening as well," she told St. Pete Rising. That "everything bouncing back" is not marketing language. It is a description of a specific commercial street that lost tenants after October 2024 and is only now, in mid-2026, refilling those storefronts with independent operators rather than chains or vacant windows.
49th Street South is becoming a second commercial spine
The more interesting change is not on Beach Boulevard at all. It is a few blocks north, on 49th Street South, where two openings in the last two months have shifted the character of the street.
The first is Arcana, which held a grand opening June 14 at 1303 49th St. S., offering tarot readings, astrology readings, reiki healings, and mediumship in what its owners describe as "our little corner of magic." The shop keeps a tight schedule, open Tuesday through Saturday from noon to 6 p.m., which tells you something about who it is built for. It is not a tourist-hours operation. It is set up for people who already live in walking or short-drive distance.
The second is a subtraction that opened a new opportunity. Coastal House Vintage, which had been at 919 49th Street South, closed that Gulfport shop on April 25 and moved to a larger space in St. Pete's Grand Central District. The new location at 2820 1st Avenue North grew from roughly 500 square feet to about 1,700 square feet in a 1926-built home converted for commercial use, and the concept expanded to include a craft cafe. The Gulfport space it left behind is now available, on a street that is quietly building critical mass for the kind of daytime browsing that used to only happen down on Beach.
The pattern to watch on 49th is not any one shop. It is that the businesses opening there are the kind that need repeat local customers rather than weekend foot traffic. That is a different economic model than Beach Boulevard's, and it changes what the street will look like a year from now.
A returning name that most residents will recognize
For anyone who lived through the last decade of downtown St. Pete, the biggest news of the Gulfport summer is a name coming back. Longtime St. Pete favorite Moon Under Water is reopening in early 2026 at 2832 Beach Blvd. S. in Gulfport, bringing back its famous curry, bangers, and fish and chips. The pub closed its Beach Drive location in downtown St. Pete about five years ago, and the return has been in the works for a while.
The Gulfport building has its own recent history worth remembering. The space became available following the closure of The Drunken Taco, which had operated in the building for two years. The team behind the revival is a mix of the original leadership and new local partners: former executive chef Mike Crippin, his wife and former HR manager Alison Crippin, and Grand Central Brewhouse owners Kevin and Jeanne Milkey. The reworked footprint will include a traditional British pub front, a London-style gin bar in back, and a sports area with roughly 20 screens, which is a genuinely new format for a Beach Boulevard address.
Two details are worth the trip if you already know the old Beach Drive version. First, including the courtyard, the new location will be nearly double the size of the original restaurant. Second, the choice of Gulfport over St. Pete was deliberate. "We initially looked in St. Pete, in the EDGE District and Grand Central District. But nothing felt quite right until the opportunity in Gulfport came along," Kevin Milkey told St. Pete Rising. Read that sentence again if you have been in Gulfport a long time. Operators who used to default to downtown St. Pete are now choosing Beach Boulevard first.
What to circle before Labor Day weekend
The late-summer calendar is short but the dates matter, because they set the traffic and parking pattern for the whole neighborhood.
- Saturday, September 5 is the anchor. GeckoFest takes over 3000 Beach Blvd. S. from 10:00 a.m. to 8:00 p.m., and the setup begins at 6 a.m. that morning. If you live within a few blocks of Beach, this is the day to move your car early if you want it accessible. This is the 25th annual GeckoFest, and the 2026 theme is "Still Weird," which is being framed as a celebration of the small independent shops and galleries that make up the downtown strip.
- The week before brings the Gecko Ball at the Gulfport Casino. If you have never gone, it is the costume-and-coronation kickoff to the festival week, and it is where a lot of the neighborhood's small business owners actually cross paths in one room.
- 6:00 p.m. on GeckoFest Saturday is the walking parade, which is followed by a birthday moment for G. Gordon McFly, Gulfport's newest sculpture and an instant iconic photo op, designed by our talented local marine artist, Ray Domingo. If you have not yet walked past the sculpture in daylight, this is the excuse.
- All summer, the Gulfport Merchants Chamber of Commerce is running the run-up Gecko World events. A portion of proceeds this year goes to the Tampa Bay Butterfly Foundation, the Sonia Plotnick Health Fund, and one additional community recipient.
One practical note that longtime residents will already know but newer neighbors sometimes miss: GeckoFest closes Beach Boulevard from the marina end up to the intersection with 49th Street area cross traffic, and the courtesy shuttle system runs from off-site lots. If you plan to shop or eat at any of the new spots on Beach that day, walk in, do not drive. If you want to introduce someone to Drift + Story or the incoming Moon Under Water space, GeckoFest is the day the whole street is at maximum energy, and it is also the day the sidewalks are hardest to move through.
Why the map has shifted, and what to watch next
The through-line for all of these openings is that Gulfport's storefront turnover is still being driven by two forces that started in late 2024 and have not finished playing out. The first is the hurricane-related closures, which knocked out tenants like Paw Paw's and reshuffled where independent operators could get a lease on Beach Boulevard. The second is the pull of Grand Central District in St. Pete, which has taken longtime Gulfport shops like Coastal House Vintage into bigger spaces but has also, in the case of The Moon Under Water, been passed over in favor of Gulfport by operators who wanted the smaller street and the parking.
If you are trying to guess what the fall will bring, the storefronts to watch are the ones that opened up in the last two months rather than the ones that have been vacant for a year. Drift + Story on Beach and Arcana on 49th both signal owners who chose to open with limited hours and specific customers in mind, rather than trying to catch tourist traffic. That is a Gulfport-shaped bet on Gulfport, and it tends to be a good leading indicator for what the next round of tenants looks like.
For now, the practical takeaway is small and useful. Walk Beach Boulevard from the pier back up toward 49th and take a look at the storefronts you last paid attention to a year ago. A surprising number of them have someone new behind the counter, and a couple of them have someone you already knew, in a new address. It is a good summer to reintroduce yourself to your own street.
If you have questions about a specific block, a specific building, or how any of this is affecting the tone of the neighborhood you already call home, The Waugh Group has been walking these streets in Pinellas County for more than 25 years. We are always happy to talk about Gulfport, no appointment required. Schedule a free consultation whenever you're ready.
