Two years after Helene and Milton, the Circle is not the same place it was in September 2024. It is not diminished, either. It is reshuffled. The tenants that closed have been replaced by larger operators, the tenants that stayed have moved into better addresses, and the fall 2026 calendar is the first full season where residents get to see the new lineup at working volume. If you live on St. Armands, Lido, Bird Key, or the south end of Longboat, here is what has actually changed in your walking and driving radius, and what is worth putting on the calendar between now and Thanksgiving.
The 300 John Ringling shuffle
The single biggest change on the Circle is happening at one address. Until late 2024, the location at 300 John Ringling Blvd. was the home of Tommy Bahama, which relocated to 465 John Ringling Blvd. in the former Shore restaurant spot after the hurricanes. That vacated corner is now spoken for. Pinchers, a seafood restaurant with 10 locations around the Gulf Coast, 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.
The target date is specific. "We are shooting to be open in October," Pinchers vice president of marketing Kevin Rooney told the Business Observer. For residents, the practical read is this: a full-service crab-and-shrimp house is landing in an 8,000-plus square-foot box at the north edge of the Circle, and the nearest comparable Pinchers today sits in Lakewood Ranch. Pinchers has 10 restaurants along the Gulf Coast, from Naples to Wesley Chapel. The closest to St. Armands are in Lakewood Ranch and Venice, about 14 and 20 miles away, respectively. If you have been driving across the bridge to Lakewood Ranch for that specific format of casual seafood, you will not need to after October.
One detail worth holding onto if you follow commercial real estate at the Circle: several LLCs based in Michigan are the owners of 300 John Ringling Blvd, after purchasing it for $8 million in 2022, according to Sarasota County property records.
The return at 22 S. Boulevard of the Presidents
The other headline for residents is a reopening, not an opening. Le Colonne, an anchor of the Circle's Italian dining for decades, closed after the storms. It has come back under a new name at the same address. Nōnnō Umberto, an Italian seafood and steakhouse, is located at 22 S. Boulevard of the Presidents. The naming is a family gesture. 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.
The soft opening was not soft.
The owners of Nōnnō Umberto 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.
Eight hundred covers in seven days is a signal about pent-up demand on the Circle after two seasons of interrupted service. It is also useful context for how the rest of the fall will trade. If you have been on the fence about a reservation, the family also kept their bridge business running through the closure. To keep the business afloat, Simone and Mayner opened an Italian food truck called Buonissimo Mobile Italian Kitchen last year.
A block north, the newer Neapolitan operator continues to hold the second-story balcony seats. 15 South By Napulè sits at 15 S. Boulevard of the Presidents with a downstairs family room and an upstairs bar program, and the kitchen runs on Neapolitan-style woodfired pizza from a gold-tiled oven under chef Giancarlo Di Cosmo.
The fall calendar, in one place
The Circle's event schedule this fall is denser than most residents realize until they miss two of them. Rather than string these across paragraphs, here they are on one line each so you can put them on the fridge.
| Event | Date | Where |
|---|---|---|
| 4th Annual St. Armands Circle Art Festival with Craft Marketplace | Sept 19–20, 2026, 10 a.m.–5 p.m. | St. Armands Circle Park |
| St. Armand's Circle Fall Art & Craft Show | October 2026 | Circle Park |
| Pinchers grand opening (target) | October 2026 | 300 John Ringling Blvd. |
| Fright Night, 17th year | October (Halloween week) | The Circle |
| 37th Annual St. Armands Circle Art Festival | Nov 14–15, 2026, 10 a.m.–5 p.m. | S. Boulevard of the Presidents and Circle Park |
| Exotic Cars on the Circle, Jaguar Festival d'Elegance | Rolling fall/winter Sundays | Circle Park |
A note on the November show, which is the largest of the fall. Each year, 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. Two hundred booths on Boulevard of the Presidents is a scale worth planning parking around. If you live inside the Longboat Club gates or on Bird Key, expect the Ringling Causeway to move slowly between 10 and 2 on both days.
For the Halloween crowd, Fright Night, in its 17th year, returns for the young, and spooky at heart. The Circle Association's event page is the source of truth for the final date and street-closure map.
Where residents actually eat between events
Once the tents come down and the streets reopen, the everyday dining question is what a fall Tuesday looks like. Four venues carry a disproportionate share of resident traffic.
Cirque St. Armands. The resort's culinary program has expanded into three distinct rooms, which matters if you want a drink versus a full dinner without leaving the property. Cirque St. Armands is home to Sarasota's newest and most creative restaurant: Ringside, which also services Midway, the lobby bar lounge, and Ringmaster, the pool bar. Expect inventive dishes in the main restaurant, then light bites and daring cocktails in the bars.
Drift Kitchen & Bar at Lido Beach Resort. For residents who want a Gulf view without giving up a walkable dinner, Drift Kitchen & Bar is located on the 8th floor, featuring 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.
Crab & Fin. The Circle mainstay continues to run two everyday value windows that residents lean on more than visitors do. The early dining discounted menu runs nightly 4:45 to 5:45 p.m. seven days a week, when most entrees are offered at a 20% discount, with a complimentary soup or salad and coffee and tea included. Happy Hour is available at the bar from 4 to 6 p.m. seven days a week, with all craft cocktails, spirits, beer and wines offered at 50% off.
Columbia Restaurant. The Cuban-Spanish anchor at 411 St. Armands Circle remains the default for large-party reservations and out-of-town guests who want a Sarasota history lesson with dinner.
The bigger read for anyone who lives here
Take the three moves together. Tommy Bahama did not leave the Circle after the storms, it upgraded to a former restaurant footprint. Le Colonne did not close permanently, it came back as Nōnnō Umberto and served 800 people in its first week. The 8,000-square-foot vacancy at 300 John Ringling did not linger, it was leased to a multi-unit operator that has been waiting for a location on the Circle. This is not a district in retreat. It is a district where the tenants absorbing the space are, on average, larger and better capitalized than the ones they replaced. For residents, that trades some of the small-shop texture that made the Circle in the 1990s for a schedule of tentpole events and dining rooms that will run reliably through the season. Whether that trade suits you is a personal question. That it is happening is not.
If the shape of the Circle is changing what you want your next home to look like, whether that means trading up to a Longboat Key gulf-front condominium, right-sizing into a Bird Key waterfront, or timing a sale to the season now filling out around you, The Koy Group is happy to walk the block with you and talk through what your address is worth in this market. Request a home valuation when you are ready.