St. Armands Circle's Holiday Season Is on the Calendar. Its Next Restaurants Aren't Yet.

"We are shooting to be open in October," Kevin Rooney of Phelan Family Brands told the Business Observer in June. He was talking about Pinchers, the seafood restaurant going into 300 John Ringling Blvd. By the time the Circle's November events arrive, that target month will have passed. The November calendar, meanwhile, was set long ago, the same way it was last year and for decades before that.

That is the shape of the Circle this season. The restaurants and shops are still shifting from one address to another as businesses rebuilt after the 2024 hurricanes settle into new spaces. The events stay put. The 48th Holiday Night of Lights is on Dec. 4, and Porsches in the Park returns for its 22nd year on Dec. 12. If you live on Lido Key, St. Armands, Bird Key or the south end of Longboat Key, here is where things stand going into the holidays.

One chain of moves, four addresses

The current changes make the most sense as a series of moves, each one opening space for the next.

• 465 John Ringling Blvd. Shore closed this location after the 2024 hurricanes. Owner Tom Leonard still owns the building and now leases it to Tommy Bahama.
• 300 John Ringling Blvd. Tommy Bahama was here until late 2024, then moved to the former Shore spot. Pinchers has leased more than 8,000 square feet in the old Tommy Bahama space.
• Boulevard of the Presidents at Madison Drive. This is where Shore wants to come back, in a rebuilt building on a different corner.
• 380B St. Armands Circle. Sloan's Ice Cream is planning its first Sarasota location here. The Sarasota Herald-Tribune reports a target of the first quarter of 2027.

The same thing happened just over the bridge. The Lido Key Tiki Bar reopened on June 20 at the Ritz-Carlton Beach Club. Juan Cordoba, the club's director of operations, told Your Observer that storm damage and permitting kept it from rebuilding in exactly the old location. Places people know came back in new spots, not their old ones.

What Pinchers is bringing to the old Tommy Bahama space

Pinchers started in 1997 as Pinchers Crab Shack in Bonita Springs. It is one of more than a dozen restaurant brands in the Phelan Family Brands group, which also runs Deep Lagoon and Texas Tony's Rib & Brewhouse. Rooney said the St. Armands location would bring the company to 27 restaurants on the Gulf Coast.

The plan calls for about 200 seats and 75 to 100 employees. Rooney described the mood as "relaxed" and "always family-friendly," and expects plenty of diners in flip-flops. That is a much more casual use of a big corner space that for years held a retail store and restaurant. With 200 seats, it will also be one of the larger dining rooms on the Circle.

The October target came from the company in June, and the Herald-Tribune repeated it in early July. Before you build a dinner around it, check the restaurant's own channels to make sure the doors are open.

Why Shore's new corner is still on paper

Shore's return is moving more slowly, and the reasons come down to how the building fits the Circle's zoning. Leonard and the Kaufman development family want a three-story building at Boulevard of the Presidents and Madison Drive. The ground floor would hold a boutique shop and a casual café, the restaurant would be on the second floor, and the third floor would be residential. The site is currently a gutted two-story shell.

Your Observer reported on Oct. 21 that three issues came up when the plan went back before the city's Development Review Committee on Oct. 7:

1. Height. The way the team plans to build the ground floor limits the building to 35 feet in the Circle's Commercial Tourism zone district, the only district of its kind in the city. A three-story plan needs more room than that.
2. The balcony. The design puts outdoor dining on a second-floor balcony over the sidewalk. City staff are treating the balcony like an awning, and awnings can't extend past the property line.
3. Parking. The building needs 17 on-site spaces, and the plan shows 11. The partners are talking with the city's Parking Division about leasing more spaces in the garage next door at Madison and North Adams drives.

A city spokesperson told the Observer, "The next step for this site plan is for the applicant to resubmit." That puts Shore's return on the city's review schedule, which means it won't open this holiday season.

The dates that don't move

Next to all those open questions, the St. Armands Circle Association's calendar is fixed. Every remaining event this year has a date, hours and years of history behind it:

The November festival uses St. Armands Circle Park and South Boulevard of the Presidents. Your Observer reports that Howard Alan Events expects about 200 artists. It closes out a busy fall for the park lawn. Howard Alan Events opened the art season there in September. Paragon Festivals brought several dozen crafters in mid-October, and Blue Ribbon Events held its Fall Art and Craft Show on Oct. 24 and 25. The sidewalk sale part of the weekend means the shops get involved too, which matters more in a year when several storefronts are between tenants.

The Holiday Night of Lights is the clearest example of how long these events have been around. Forty-eight years is longer than nearly any storefront on the Circle has kept the same tenant. In past years, according to Sarasota Style, the evening has included a Santa parade, photos with Mr. and Mrs. Claus, caroling and the lighting of a 60-foot tree. So far the Association has posted only the date and hours for 2026. Check its events page for the full program closer to Dec. 4.

Getting over the water this season

Driving to any of these events from the mainland takes you over the John Ringling Causeway, where cones and equipment have been part of the trip all fall. The $12.3 million project adds bus-only lanes and dedicated bike lanes, improves drainage, resurfaces the road and installs new traffic signals. In its Oct. 9 report on the joint Sarasota and Longboat Key commission meeting, Your Observer said the work should wrap up later this year. In April, the same paper listed completion as early 2027, so the finish date has shifted before.

The longer project is the Little Ringling Bridge, the short span between the causeway and the Circle. Design work costs $4 million, and the bridge itself is expected to cost about $74 million. Construction isn't expected to start soon. Expect to cross the current bridge for every event on this year's calendar.

For parking, the city's St. Armands garage has 484 spaces. On a festival weekend it is usually simpler than circling for curb spaces near Circle Park. For a beach stop before or after, Lido Key got 300,000 cubic yards of sand this year from the New Pass dredge, under the sand-sharing agreement between the city and Longboat Key.

How the season lines up

Ferraris on the Circle and the November art festival will come and go while Pinchers works toward opening. The Night of Lights tree will be lit while Shore's plans are still going back and forth with city staff. When Sloan's opens at 380B St. Armands Circle in early 2027, Porsches in the Park will already be over for the year.

Monica Verinder lives and works a short drive from the Circle and follows every change of address on John Ringling Boulevard. If you're thinking about what these changes mean for a home on Lido Key, St. Armands or Bird Key, Monica Verinder would be glad to talk it through. Schedule Your Private Consultation.