All summer, Sheila Loccisano went to the Longboat Key Historical Society cottage on Town Center Green every Thursday at noon and filmed herself at the door for her "Follow Me to Longboat Key" Instagram page. As the Longboat Observer reported, each video ended at a locked door, with a selfie in front of a sign promising Thursday-through-Saturday hours. One Thursday in October, the doors were propped open.
That small reopening explains the whole Green this season. Nearly everything happening at 600 Bay Isles Road this November depends on an island organization, a volunteer or a donor. The one piece that doesn't, a planned Sarasota County library, is the piece still waiting on a decision made off the island.
The Cottage Reopened Once Someone Explained the Locked Door
The rumors about the society shutting down turned out to come from a missing sign. Society President Michael Drake told the Observer that a notice with his name and phone number, saying the cottage was closed for the summer but open by appointment, had disappeared. Regular hours resumed in October, Thursdays through Saturdays from 11 a.m. to 1 p.m., and Drake plans to extend them during the busy season if enough volunteers sign up.
The building has its own history. It began as the linens and laundry cottage of the Whitney Beach Resort, which was built in 1926, and it was moved to the Green in 2021. Inside are:
- Photographs described as the earliest known images of Longboat Key, dated 1914 to 1920, plus pictures from the 1953 fish fry
- Bound copies of the Anna Maria Islander from 1963 to 1976
- Ralph Hunter's From Calusas to Condominiums and Lora Colvin Whitney's Hail This Feisty Village!
- Plaques that once hung on post offices and bridges, including one with John F. Kennedy's name
- A preserved skin from an eastern diamondback rattlesnake killed on the island decades ago
The society's requests are practical. Donations would pay first for a new front door and fascia repairs, then for display modules to show more of the collection, and they also cover ongoing costs such as electricity and insurance. Volunteers are the other need. Loccisano told the Observer she already knows of at least 10 people willing to help staff the cottage. The society also hopes to get 602 Bay Isles Road as its own address. It sits behind the Karon Family Pavilion.
November's Two Evenings, Both Run by Island Organizations
The pavilion turns three in November. The Karon Family Pavilion was dedicated on Nov. 11, 2023, with a ribbon cutting and the Sarasota Orchestra Brass Quartet's first performance there. Since then the Green has held community open houses with town departments, food trucks and local groups, and last November it hosted the town's 70th-anniversary and Veterans Day program.
This November has two evenings on the calendar, each run by a different island organization.
| Laughs On Longboat | Light Up Longboat | |
|---|---|---|
| Date | Thursday, Nov. 12 | Saturday, Nov. 21 |
| Time | 4:30 to 8:30 p.m. | 5 to 7 p.m. |
| Organizer | Longboat Key Foundation | Longboat Key Chamber of Commerce |
| What's planned | Live music, four comedians, food trucks | Food vendors, music, tree lighting, prizes |
| Cost | $35 per person, table and chairs included | No public admission price listed |
At Laughs On Longboat, Akiem Esdaile plays from 4:30 p.m., and the four comedians start at 5:30. The Chamber listing says the $35 ticket includes complimentary beer, seltzers, water and tea, and reserved tables are available for groups of eight or ten. The town's event page lists the Longboat Key Foundation as the contact and links to the Foundation's site for tickets.
Light Up Longboat is paid for by local businesses. The Chamber is selling sponsorships at $75, $150 and $300, with $300 also buying the music-and-sound sponsorship, plus $35 vendor tables. Its listing says that money pays for the decorations and lights that turn the Green into a holiday setting. The Observer's account of the 2025 event describes caroling, Santa, local vendors, a Rotary raffle for HOPE Family Services and a countdown to the tree lighting.
Both November evenings are in the late afternoon and early evening. That timing matters for the building planned next door.
Around the Green, Between Events
On Bay Isles Parkway, Reed Medical Group and Longboat Key Fitness reopened in expanded space at the Shoppes of Bay Isles in January. Reed's address is now 509 Bay Isles Parkway. Secur-All Insurance moved to 510 Bay Isles Road after its earlier north-Key office was damaged in storms.
Farther along Gulf of Mexico Drive, Longboat Key Provisions opened at The Centre Shops, 5370 Gulf of Mexico Drive, Suite 103, in December 2025. It took the space David Gregory Salon left that summer. At The St. Regis Longboat Key Resort, AGCF, the boutique founded by Alexandra Gucci Zarini, has announced a second location in the lobby for "later this fall," according to the Observer. It will carry handbags, leather goods, scarves, jewelry and eyewear.
There's also art on the island this month. Ringling College graduate Tori Abramov's first solo exhibition is at All Angels by the Sea Episcopal Church through Nov. 29, and the Observer reported that it includes scenes of Town Center Green.
The Building the Island Raised Money For
The Green's biggest project follows the same pattern as the cottage and the two evenings, up to one point. The Observer reported in September that Sarasota County is putting $11 million into the planned library, $1 million for design and $10 million for construction. Separately, the town and the Longboat Key Foundation raised donations to expand the building with event space. Their goal was $3 million, and according to the town-county funding agreement they raised $3.8 million, including a $1 million pledge from U.S. Rep. Vern Buchanan. The county had already received $1.6 million of that total by September.
Because of those donations, the 11,324-square-foot building will include an enlarged community room for special events, which county staff said can seat 200. The room is also why the Town Commission spent time on parking, according to the Observer's October report. The 78 spaces east of the Green are twice the 39 the town code requires for daily library use. For larger events, town staff counted 603 more spaces in nearby lots, including Mediterranean Plaza, the post office, churches, banks and the tennis center, all usable only with each owner's permission. Assistant Town Manager Isaac Brownman said those lots may have spare capacity "especially for late afternoon or early evening events, and especially for weekend events," the same times as this month's comedy night and tree lighting. Any event expected to need more than about 681 spaces would require its organizer to file a parking and transportation plan before getting a permit.
The commission gave the site and development plans first approval on Oct. 5 and scheduled the final vote for Nov. 2. The construction decision rests with the county. Before the Nov. 3 election, Sarasota County said it would not build a library on Longboat Key "at this time" if voters approved Amendment 3, a statewide measure to reduce property taxes, while it kept moving ahead with design and permitting in the meantime. Former Town Manager Howard Tipton said groundbreaking was scheduled for March. He also said that if the amendment passed, "we'll have to figure out how to refund the money that's been raised." The election result and the commission's Nov. 2 vote decide which of those two paths the project takes.
For now, the cottage is open Thursday through Saturday from 11 a.m. to 1 p.m., the comedy night is Nov. 12, and the tree lighting is Nov. 21. Everything else on the Green's calendar waits for the county.
Fuller Group follows how the island's shared spaces grow, from a reopened cottage to a library that may come next. If you'd like to talk through what the next few seasons could bring to the Bay Isles corridor, Fuller Group welcomes you to arrange a private consultation.
