Siesta Key Village’s New Restaurants and Shops: Who’s Behind Them?

"We're seeing an upscaling of Siesta Key Village," a senior investment advisor with SVN Commercial Advisory Group told a reporter for Siesta Sand a while back, describing what happens to a beach town's commercial strip once national retailers start signing leases. He wasn't wrong. He also wasn't describing something new. He was describing something still in motion, and if you live here, you've watched it happen without necessarily connecting the dots.

Walk Ocean Boulevard on a Saturday and the Village looks busier than ever. More menus. More storefronts with fresh paint. More reasons to park twice before you find a spot. Several Village restaurants and retailers are connected to a small number of operators.

Restaurants connected to Above the Bar

Start with Avenida Messina and Ocean Boulevard, the busiest intersection in the Village. If you've eaten at Beach Club, Summer House Steak & Seafood, The Cottage, or The Hub Baja Grill, you've spent money with the same company. All four belong to Above the Bar Hospitality Group, the umbrella business built by longtime Siesta Key operators Chris Brown and Mike Granthon.

That footprint has only grown. Siesta Poke, the build-your-own poke and açaí spot next to Made in Rome Organic Gelato, is also a Brown and Granthon project, run under the same group with Katie Spelman overseeing operations. And MVP, the sports bar that took over the old Napoli's Italian Restaurant space at 5200 Ocean Blvd, brought in a third partner, Peter Geannopulos, previously the owner and chef of Hillview Grill and an investor in Mad Moe's Pub and Grill in Osprey. MVP has been open long enough now that it has its own regulars and its own reputation.

The table below lists six businesses connected to Above the Bar Hospitality Group, including MVP, which also has Peter Geannopulos as a partner.

The group's reach extends off the island too. Smokin' Joe's in downtown Sarasota and Mad Moe's Pub and Grill in Osprey both belong to the same partnership.

Not everything new in the Village fits that pattern. The Duo Doner & Deli, tucked into the Siesta Center across from what used to be Davidson Plaza, is an independent shop run by chef Jakub Skoczylas and his wife Maja Rakowiecka, a couple who moved from Poland by way of Sweden and the U.K. before Skoczylas worked as executive sous chef at the Founders Club and eventually opened their own place. It is one independent business among the recent food openings described here.

The pharmacy that held the plaza together for 65 years

The retail side of this story runs on a slower clock, but it's the same shape.

For decades, Davidson Plaza was anchored by Davidson Drugs, an independent pharmacy that had served the island since 1958. When it closed for good, the announcement caught longtime residents off guard. The pharmacy operation moved to Walgreens locations off the island, and the family that ran it, three generations deep by the end, described it as the end of an era brought on mostly by declining prescription reimbursement rates, a pressure that has squeezed independent pharmacies well beyond Siesta Key.

What came next was a rename and a re-tenanting. Davidson Plaza became Siesta Village Plaza, and the mix of businesses filling in the vacancies looks nothing like the plaza it replaced. Southern Tide, a sister brand to Lilly Pulitzer and Tommy Bahama, opened next door to Lilly Pulitzer, which had already been a tenant since 2019. Kilwins, the national ice cream and confectionery chain, took the corner store fronting Ocean Boulevard. Sea Bags Maine, which makes bags out of recycled sailcloth and operates roughly 40 locations in coastal towns, opened between Local Bean Coffee & Tea and Siesta Village Dentistry. Rochelle's on Siesta, a boutique with locations in Newport, Watch Hill, and St. Armands Circle, moved into the space the Siesta Key Chamber of Commerce had occupied for 25 years before the Chamber relocated to its own larger building on Avenida Navarra. Comfort Shoes Birkenstocks & More, a business that's served Sarasota for more than 30 years, shifted to the former Edward Jones storefront. And the old Davidson Drugs space itself, more than 10,000 square feet at the plaza's southern end, is under construction to become an Alvin's Island store.

After Davidson Drugs closed, the plaza added regional and national businesses, including brands with other Gulf Coast locations.

The same SVN advisor who described the "upscaling" put a number on what it means going forward, at least directionally: more national retailers coming in, he said, raises the value of both the retail and residential market on the Key. He also flagged the tradeoff nobody disputes. Parking, already tight, isn't getting easier as more traffic gets pulled into a fixed number of blocks.

How the changing mix shows up for residents

None of this means the Village is losing its character overnight. For residents, the changing business mix is one visible part of the Village’s character.

The restaurant connections described above sit alongside a retail mix that includes national and regional brands as well as independent businesses.

The Siesta Key Farmers Market is another feature of the Village. It sets up every Sunday from 8 a.m. to 1 p.m. in the parking lot of what's now Siesta Key Village Plaza, the same lot that used to belong to Davidson Plaza. It's still independent vendors selling local and organic produce, prepared food, and handmade crafts, rain or shine, year round.

The weekly market provides a recurring place for independent vendors within that wider mix.

If you're weighing what any of this means for property values on the Key, whether you're thinking about buying, selling, or simply trying to understand how your own neighborhood is shifting, the team at The VanDuren Group tracks these changes as part of daily work in this market. Request your white-glove consultation and get a read grounded in what's actually happening on the ground, not just what the listing photos show.