If you have lived on Longboat, Lido, or St. Armands for more than a season or two, you already know the rhythm of the Circle. You know which windows go dark in August and which parking spaces open up first after Easter. What you might not have tracked is how much of the tenant roster has quietly turned over in the last twelve months, and how little of that turnover shows up when you drive past at 25 mph.
The short version: the Circle is not recovering from Helene and Milton so much as re-sorting. Legacy names are coming back under new banners, and a handful of independent operators have moved into anchor addresses that used to belong to national brands. If you have been waiting for the Circle to "feel normal again," this fall is probably the closest it has looked to a full deck since 2023, and the mix on that deck is genuinely different.
The story is not who is back. It is who is back under a different name, and who took the spot they used to have.
Addresses you know, tenants you don't
The most visible shuffle is at 300 John Ringling Boulevard, the corner that spent years reading as Tommy Bahama. Tommy Bahama vacated in late 2024 after the storms and relocated to 465 John Ringling Blvd. in the former Shore restaurant spot after the hurricanes. The old flagship space did not sit empty for long. Pinchers signed a lease for more than 8,000 square feet at 300 John Ringling Blvd. in Sarasota, where it plans to begin serving customers this fall, with an October target confirmed by Kevin Rooney, vice president of marketing and advertising for Phelan Family Brands.
Two things are worth pulling out of that. First, Pinchers is not a boutique concept: it is a ten-location Gulf Coast chain out of the Phelan Family Brands group that also runs Deep Lagoon and Texas Tony's. Second, until this lease, the closest Pinchers to St. Armands were in Lakewood Ranch and Venice, about 14 and 20 miles away, respectively. Signing an 8,000-square-foot lease on the Circle when your closest sibling location is Lakewood Ranch is a bet on year-round traffic, not just tourist volume. That is a useful tell for anyone reading the market.
A quieter version of the same story is happening at 7 N. Boulevard of the Presidents. St. Armands Jewelers is taking the place of Jewelry by Cole with new ownership. The closed shop's namesake master goldsmith, Stephen Cole Powell, began handcrafting fine jewelry in 1974. He co-owned the shop with Karyn Powell. The new operator is Mia Tohar Eylon, and the transition is being helped along by Diane DelloRusso, who has worked in the jewelry business for 36 years and been a longtime manager at Jewelry by Cole. She came out of retirement to assist with the transition. If you have walked past that corner for a decade assuming the same case layout, expect a different showroom this season.
Reopenings that aren't quite reopenings
Le Colonne was a Circle fixture for years. It is not coming back. What is coming back, at the same address, is Nōnnō Umberto, and the distinction matters if you are the kind of resident who tracks these things by name rather than by storefront.
When hurricanes Helene and Milton forced the family to close Le Colonne, they didn't know what the next steps would be. To keep the business afloat, Simone and Mayner opened an Italian food truck called Buonissimo Mobile Italian Kitchen last year. The rebrand followed. Nōnnō Umberto, an Italian seafood and steakhouse, is located at 22 S. Boulevard of the Presidents, and the reopening in early January was louder than anyone planned: the owners expected a fairly quiet soft opening for the rebranded Italian restaurant on St. Armands Circle the first week of January. But it was anything but quiet as staff served more than 250 people on the first night, growing to 800 people over the course of the first week, according to co-owner Amber Mayner.
The naming choice reads as intentional. Mayner and Simone decided to reopen the restaurant under the new name, recognizing the legacy of Simone's father, Umberto Salustri, who opened the original Le Colonne. Same family, same corner, different concept. That is the pattern to watch this year.
Independents filling in around them
The other half of the turnover is smaller operators moving into spaces that used to belong to established shops or national chains.
At 410 St. Armands Circle, the newest addition to St. Armands Circle's business community, a lifestyle and clothing brand, opened last week. The Sarasota Style, after holding a soft opening earlier this month, held ribbon-cuttings with the Sarasota Chamber of Commerce on Jan. 14 and the Longboat Key Chamber of Commerce on Jan. 16. The store celebrates everything Sarasota with its branding on clothing, water bottles, beach towels and more. The shop keeps generous hours for a Circle tenant, open from 9 a.m. to 9 p.m. daily at 410 St. Armands Circle, which tells you something about how the owner reads evening foot traffic on this stretch.
Chocolate Emporium is the second-store story. Liv Baker's first job was working at a chocolate shop, and she quickly found she had a talent for slinging sweets. Now, as the store manager of the original Chocolate Emporium on Anna Maria Island, she is putting that love for lollies to use in helping pilot the next steps for a multistore brand with the opening of a second location on St. Armands Circle. The read on the two spaces is instructive for anyone trying to understand who the Circle is now catering to. "On Anna Maria, you can sit down for an ice cream or a coffee," Kevin Schreiner said, explaining that St. Armands is more tailored to the on-the-go shopper. However, the second location still carries plenty of favorite treats from the original shop.
That framing, Anna Maria for sitting down and St. Armands for walking through, is a small comment with a larger point behind it. Operators are treating the Circle as a stroll-and-buy district first, a linger district second. If you have wondered why more benches and pocket seating have not materialized in the retail zones, that is your answer.
Worth noting alongside these openings: the pocket park between The Met and Le Colonne remains a real amenity for anyone treating the Circle as a walking loop, with a park on the Boulevard of the Presidents located between The Met and Le Colonne, the space includes artificial turf, rocking chairs, and a larger-than-life chess set.
The calendar to actually put on your fridge
The retail turnover matters more when you overlay it against the fall and early-winter event calendar. This is the stretch when the Circle earns most of its shoulder-season foot traffic, and when the new tenants get their first real test.
| Event | Date | Notes |
|---|---|---|
| 4th Annual Fall Art Festival with Craft Marketplace | Sept 19–20, 2026 | Two days on the Circle, national and local artisans |
| 17th Annual Fright Night | Oct 31, 2026 | Free trick-or-treat around the Circle, storefront decorating |
| Pinchers grand opening (target) | October 2026 | 300 John Ringling Blvd, former Tommy Bahama |
| 37th Annual St. Armands Circle Art Festival | Nov 14–15, 2026 | Roughly 200 artists, Howard Alan Events |
A few specifics for planning. The September show is the smaller of the two art weekends: over the course of two days, attendees will have the opportunity to explore creations from the finest local and national artists and crafters, including both established festival favorites and emerging talents in the contemporary art scene. The November festival is the bigger production, with the St. Armands Circle Art Festival showcases the talents of 200 artists, featuring a diverse range of artistic mediums such as sculpture, photography, glasswork, paintings, ceramics, jewelry, mixed media, and more.
Fright Night is on Halloween itself. The 17th annual Fright Night takes place from 6-8:30 p.m. Oct. 31. Youngsters can trick or treat around the Circle, while the whole family can enjoy taking in the sight of decorated storefronts.
Parking, as ever, is the friction point. The municipal garage has 504 spaces (first two hours are free, the third hour is $3 and each additional hour is $1 or part thereof) and there are 197 surface lot spaces in the lot on South Adams Drive (cost $1 per hour), and there are 186 FREE unrestricted parallel and diagonal parking spaces located north of Madison Drive on No. Boulevard of the Presidents and south of Monroe Drive on So. Boulevard of the Presidents (3-hour limit). On art-festival weekends, plan on the free spaces being gone by 10 a.m.
What this shoulder season actually looks like
If you have been on the Circle only occasionally since the 2024 storms, three things will read differently this fall.
The tenant mix at anchor addresses has shifted from national retail toward regional and independent operators. Pinchers replacing Tommy Bahama at 300 John Ringling is the loudest example, but St. Armands Jewelers, Chocolate Emporium, and The Sarasota Style are all pointing in the same direction. The Circle is trading some of its recognizable-mall character for operators who chose this specific address on purpose.
The dining lineup is stratifying. Nōnnō Umberto and the coming Pinchers sit at two very different price points and two very different service models. Alongside longtime tenants and the Cirque St. Armands / Lido Beach Resort side of the equation, where Drift Kitchen & Bar, located on the 8th floor, features elevated decor and floor to ceiling views of the Gulf of Mexico, open daily for Breakfast, Happy Hour and Dinner, Drift's menu features local ingredients with an emphasis on fresh seafood and contemporary American fare, a resident now has meaningfully more range within a five-minute walk than a year ago.
The event calendar is compressing into a September-through-November window that carries most of the shoulder-season energy. If you have out-of-town guests coming in, that stretch is where the Circle has the most to offer beyond the beach.
For residents who own a home nearby, none of this changes the fundamentals of Lido, St. Armands, or Longboat. What it does change is the answer to "what's new?" when someone asks. This year, the honest answer is: quite a bit, and most of it in the last nine months.
If you are thinking about how the barrier-island market is repositioning after the 2024 storm season, or how retail turnover on the Circle is affecting nearby property demand, the team at Bruce Myer tracks this closely. Talk with us about your real estate plans.
