On Monday, September 14, Longboat Key handled more transitions in a single commission meeting than most towns manage in a year. It was Howard Tipton's last day after three years as town manager. It was George Landry's first. The Town Commission met for the first time since its summer recess, gave initial approval to a budget with a higher millage rate, and then, in Landry's first live controversy on the job, voted 7-0 to yank a long-debated tree ordinance off the agenda for more scrutiny.
Nine days earlier, a different piece of news landed with far less ceremony: the Florida Department of Transportation told the town that its long-planned roundabout at Broadway Street and Gulf of Mexico Drive, the project residents on the north end have pushed for since 2021, would not go out to bid until July 2027. Design work is finished. Money is largely secured. The bid just isn't happening yet.
Put those two stories together and you get the real shape of what changed here this month. The person now responsible for finishing the island's most argued-over intersection took the job the same week that intersection's timeline slipped again. If you live on Longboat Key, that overlap matters more than either headline on its own.
The Handoff
Landry isn't a stranger to following Tipton. He spent 13 years in St. Lucie County government, working his way from human resources and risk manager into the top job as county administrator in 2023, the same year Tipton left St. Lucie for Longboat Key. Before that career, Landry served more than 20 years in the U.S. Army, including deployments to Iraq, and earned two Bronze Stars and a Purple Heart along the way.
When Tipton told commissioners in April he'd be retiring for health reasons, he was asked to find his own replacement. He recommended Landry. The Town Commission approved a five-year contract on June 22 without a national search, at a starting salary of $255,000, a $25,000 cut from what Landry was making in St. Lucie County. The contract includes a $2,500-a-month housing allowance, $500 more than Tipton received, which the town attorney's memo attributed directly to housing costs and supply on the island.
In his cover letter, Landry leaned on a phrase he said he'd heard repeatedly while researching the job: "Keep Longboat Longboat." He framed his role as protecting the island's identity rather than reshaping it. He spent his first week shadowing Tipton, started Monday, and was fielding resident questions at a Let's Talk Longboat forum at the Bayfront Park Recreation Center by Tuesday afternoon, his second day on the job.
The Intersection He Inherited
The Broadway Roundabout has been a fixture of Longboat Key North meetings for half a decade. The problem it's meant to fix is specific: Gulf of Mexico Drive traffic doesn't stop at Broadway, but Broadway itself has stop signs on both ends, and the road curves down from a bridge just north of the intersection with a sightline that District 5 Commissioner Sarah Karon has described as genuinely unsafe for the people walking from the Village to the beach, "pulling a wagon, holding grandchildren's hands."
The project has already survived one full restart. In 2023, FDOT rejected the town's design after it was nearly 90 percent complete, citing the road's banking. That sent the town back to Kimley-Horn and Associates for a redesign that flattens the curve entirely. By late 2024, the Sarasota/Manatee Metropolitan Planning Organization agreed to move funding originally scheduled for 2030 up to 2026, and by 2025 FDOT had committed to cover most of an estimated $6 million project, with the town responsible for roughly $1.7 million in utility relocation, landscaping, and brick pavers.
Here's how the target date has actually moved over the past 18 months:
| When | What changed |
|---|---|
| February 2025 | Total cost estimate lands near $5.1 million, split between FDOT, the town, Manatee County, and the MPO |
| April 2025 | Town budgets for an added $1.7 million in utility, landscaping, and paver costs |
| January 2026 | Town staff expect design to finish by February, with bids opening in July |
| September 2026 | FDOT pushes the bid and construction-letting target to July 2027, citing budget constraints |
The design itself hasn't changed. Once built, the roundabout will carry a 25 mph design speed, a shared-use path widened from 8 feet to 12 feet, 7-foot buffered bike lanes, and a landscaped median, the first piece of the town's larger vision for the full 10-mile Gulf of Mexico Drive corridor. Maureen Merrigan, who co-chairs the Longboat Key North homeowner coalition, called the intersection "definitely a dangerous intersection" and said fixing it has been the group's top priority for five years running. The engineering is done. What's left is a state agency's bid calendar, and now a new town manager who has to keep pressing FDOT on a project he didn't start.
Two Different Clocks
While the roundabout moves on a bureaucratic calendar measured in years, the island's small business scene is running on a much faster one. The Longboat Key Chamber of Commerce holds its Membership Awards Gala on September 24 at The St. Regis Longboat Key Resort, and for the first time this year, the Small Business of the Year category includes three nominees that all opened their doors in January.
ClearView Windows and Doors opened a Longboat Key showroom at 3150 Gulf of Mexico Drive modeled on its original Bradenton store, built specifically around storm-resilient inventory in the years since Hurricanes Helene and Milton. Herb Methodology, a line of plant-based treatments developed by sisters Tryla Brown Larson and Crystal Brown from techniques their grandmother taught them, has grown enough in eight months to earn a nomination its co-owner said she didn't expect. The Sarasota Style, a home goods boutique at 410 St. Armands Circle, built its pitch around being a one-stop shop for homeowners furnishing a new place on the key.
Three businesses launched, built a customer base, and got nominated for a chamber award in under nine months. The roundabout has been in active planning for five years and still doesn't have a construction date. That's not a criticism of anyone involved in the roundabout process. State transportation funding runs through a different set of constraints than a storefront lease. But it's a useful reminder for anyone trying to read the pace of change on this island: private investment here moves fast, public infrastructure moves on FDOT's clock, and the two rarely sync up.
Chamber president and CEO Kim Verreault said this year's theme, "Honoring the Brilliance of Our Community," fits a year that saw new enterprises open and find ways to serve regulars. The gala runs 6:30 to 9 p.m., tickets are $125 and include dinner, and registration is open through LongboatKeyChamber.com.
What's Actually on the Calendar
A few dates worth knowing if you're keeping track of island business this fall:
- September 24: Chamber of Commerce Membership Awards Gala at The St. Regis, with the Small Business of the Year winner announced live.
- September 28: Town Commission's final vote on the fiscal year 2027 budget, which currently carries a millage rate increase from 1.960 to 1.999.
- July 2027: FDOT's revised target for putting the Broadway Roundabout out to bid, assuming no further budget-driven delays.
None of that changes what the intersection looks like today, and none of it changes who's running Town Hall this week. But it does tell you where to look if you want to know whether the island's newest administrator can keep a five-year-old promise moving after inheriting it from the man who made it.
If you're weighing what any of this means for a home or a rental on Longboat Key, Pointer Property Group tracks these kinds of local shifts as part of knowing the island, not just the listings on it. Reach out anytime you want a straight read on the market here.
