A crab shack for the old Tommy Bahama. Tommy Bahama for the old Shore. And Shore rebuilding itself from the slab up in flood-proof glass.
—Within roughly a mile of one another, three of the district’s marquee restaurant addresses are trading tenants, cuisines and keys in a game of musical chairs played almost entirely in shellfish. Pinchers, the Gulf Coast crab-and-shrimp chain, is moving into the old Tommy Bahama space. Tommy Bahama has already reopened in the old Shore space. And Shore — the homegrown grouper-and-boutique institution the 2024 hurricanes chased off the Circle — has filed to build itself back, this time as a fortified, three-story piece of architecture.
—Layer in the flood-proof glass now headed for at least one ground floor, effectively turning a dining room into an inside-out aquarium, and the verdict is hard to miss. A year and a half after Helene and Milton put storm surge over the island not once but twice, the Circle has answered with seafood, sweets and structural engineering.
—Musical Chairs, Played in Shellfish
—The reshuffle is easiest to follow as a set of dominoes.
—At 300 John Ringling Blvd., on the Gulf-facing end of the commercial district, Tommy Bahama ran its restaurant and store until late 2024, when flooding forced it out. That space is where Pinchers is now headed, with a target opening this fall.
—At 465 John Ringling Blvd., at the opposite end of the northeast quadrant, Shore operated until December 2024, when the same back-to-back storms shut it down. Rather than leave the address dark, Tommy Bahama relocated there — less than a mile east — and reopened for the current season.
—And at 24 and 28 N. Boulevard of the Presidents, the flood-gutted former bank buildings on the northeastern lip of the Circle, Shore is planning its return: not a re-tenanting of an old shell but a ground-up, mixed-use flagship it hopes to reopen by early 2028.
—One district. Three addresses. A near-complete turnover of tenants — and a menu that keeps coming back to the water.
—Pinchers Drops Anchor at 300 John Ringling
—The newest arrival is also the most straightforward. Pinchers has signed a long-term lease for more than 8,000 square feet at 300 John Ringling Blvd. and is aiming to open in October.
—The restaurant plans to occupy both floors, with around 200 seats and a staff of roughly 75 to 100. A small portion of the space is set aside for retail — branded shirts and the like — but the emphasis is squarely on crab, shrimp and a relaxed, family-friendly, flip-flops-welcome atmosphere a short walk from Lido Beach.
—Pinchers is the flagship concept of Phelan Family Brands, a portfolio of more than a dozen restaurant concepts that began in 1997 with the original Pinchers Crab Shack in Bonita Springs and has since grown to include names like Deep Lagoon and Texas Tony’s Rib & Brewhouse. The St. Armands location will push the group to 27 restaurants along the Gulf Coast. Of the chain’s 10 existing Pinchers, from Naples to Wesley Chapel, the closest to the Circle are in Lakewood Ranch and Venice, roughly 14 and 20 miles away.
—The property at 300 John Ringling is held by a group of Michigan-based LLCs that paid $8 million for it in 2022, according to Sarasota County records. Ripco Real Estate represented the ownership in the deal. The company’s founder is said to be personally assembling the coastal art and crabbing paraphernalia that will line the walls, and there is talk of enlarging one of the building’s two bars so the levels match.
—Shore’s Return, Reengineered
—If Pinchers is a lease, Shore is a construction project — and the newest filing spells out just how ambitious.
—The plan knits 24 and 28 N. Boulevard of the Presidents into a single three-story, mixed-use building of roughly 17,000 square feet. The ground floor would hold more than 7,000 square feet of retail plus a café of about 1,820 square feet. The second floor would house a Shore restaurant of roughly 8,500 square feet. The buildings have already been gutted, and crews are fortifying the infrastructure underneath.
—The third floor is drawn as about 4,580 square feet of residential space wrapped around a central pool, with four rooms labeled as suites and a gym in the southwest corner. For now, the plan is to build that top level as a dried-in shell — walls, doors and windows to seal it, but the interior finished later depending on timing and budget. The likely sequence: open the retail and café first, the restaurant shortly after, and leave the top floor for another day.
—The ownership structure has come into sharper focus, too. The land is held by Kauffman Shore Properties LLC, a partnership between restaurateur Tom Leonard and the Sarasota development family led by Mark Kauffman and his daughter, Mindy Kauffman. The conceptual design is mid-century modern, pitched as a deliberate complement to the Circle’s eclectic mix of older façades.
—Shore, it’s worth remembering, never fully left the barrier islands: it continues to run its bayfront restaurant and boutique at 800 Broadway on the north end of Longboat Key, a 400-foot stretch of waterfront with stadium seating and a retractable roof.
—The Inside-Out Aquarium
—The most interesting part of the Shore plan isn’t the menu. It’s the glass.
—To keep the building operational through the next storm — and to satisfy the federal flood rules that govern any major rebuild on the island — the ground floor is slated for flood-proof glass, roughly 10 feet tall and running on the order of $5,000 per linear foot. A structural slab some 20 inches thick would run the length of the building. Total cost, the developer will say only, runs into the millions.
—Done right, it makes the corner one of the first buildings on the Circle engineered as an inside-out aquarium: water can rise against the glass, and the space inside stays dry. The logic is as much fiscal as architectural. If a building survives a surge without flooding, the owner isn’t waiting on a federal recovery check afterward — and the barrier island isn’t watching another gutted storefront sit dark for two years. On a Circle that took two floods in a single season, resilience has quietly become a design philosophy.
—The Third Floor Waits for July 15
—The Shore project makes its first stop before the city’s Development Review Committee on July 15, and the third floor is the piece neighbors and merchants will watch most closely.
—St. Armands sits in the city’s Commercial Tourist zoning district, which does not currently permit hotels on the Circle. The filing describes the top floor as residential, with the long-discussed possibility that it could one day operate as a boutique hotel if the code ever changes — a prospect residents have consistently opposed and one that would require a separate, uphill approval. For the moment, the plans call for a single residence and a shell. That debate will play out at City Hall over the coming months; the rest of the Circle’s revival is already underway.
—A Quadrant Rebuilt, Storefront by Storefront
—Shore and Pinchers are the headline acts, but the fuller story is how much of the storm-battered Circle has already come back.
—On the south side of Boulevard of the Presidents — one of the district’s hardest-hit blocks — a three-unit retail building at 28 S. Boulevard of the Presidents that took heavy flood damage in 2024 has been renovated and is now fully leased. The new tenant mix reads like a snapshot of the Circle’s next chapter:
—Le Shop, an aesthetic wine-and-coffee bar pouring handcrafted coffee and tea and a selection of natural wines, with fresh pastries from local bakers and a tidy market of global snacks. It sits across from The Met and is open daily except Monday.
—Acadia Jewels, which opened in January 2026 as the first Florida location of the Maine-based jeweler.
—Flambo, a Caribbean restaurant that opened in late 2025 at 40 S. Boulevard of the Presidents.
—Nōnnō Umberto, a newly opened Italian spot rounding out the district’s dining bench.
—Vacancies that gaped after the hurricanes are filling with national chains, first-to-Florida boutiques and homegrown names alike.
—The Sweet Finish
—The capstone on that rebuilt quadrant is a sweet one. Chocolate Emporium, the popular Anna Maria Island chocolatier, opened its first Sarasota shop on the Circle in June — a 1,446-square-foot store of handmade chocolates, fresh fudge and, in a nod to the setting, saltwater taffy, all within walking distance of Lido Beach.
—The shop is an offshoot of the original on Anna Maria Island, opened by a European candy maker who decided, after a single successful year up the coast, that St. Armands had exactly the clientele for high-end confection. It was the final tenant to fill the once-battered block — the last light switched back on.
—The Bottom Line
—Strip away the individual leases and a single trend line emerges: capital is flowing back onto the most protected — and most storm-exposed — commercial acre in Sarasota, and it is betting real money that the Circle is worth not just reopening but reengineering.
—Pinchers is wagering on 200 seats and a fall opening. Shore is wagering millions on flood-proof glass and a 2028 return. A rebuilt south block is wagering on wine, jewelry, chocolate and a mix of cuisines from Caribbean to Italian. Each of them is a vote of confidence in the same fundamentals — Lido Beach next door, foot traffic that never really left, and a clientele that has the means to spend.
—Real questions remain, and they’ll be argued at City Hall well into the fall: how high, how dense, and whether “residential” stays residential. But the direction of travel is no longer in doubt. The Circle took two floods in one season and answered with crab shacks, chocolate, flood-proof glass and a table set for 200.
—It is, unmistakably, back in the water.
