Light Up Longboat lasts two hours. Christmas in the Garden runs for 33 nights. Those two events bracket the island's holiday season, and they have something in common. Neither one is a resort production. Both are put together by neighbors and local groups, and both are listed as free.
Almost everything else on the Longboat Key calendar between now and New Year's Eve follows the same pattern. A congregation hangs its members' art. The Garden Club hosts a design night in the town's recreation center. A Chamber member enters the Sarasota boat parade. Apart from a Chamber networking night and a Garden Club class, the parts that need a reservation and a credit card are at the resorts, during Christmas week and on New Year's Eve.
Saturday, Nov. 21: The Oaks at Town Center Green
The season starts with Light Up Longboat on Saturday, Nov. 21, from 5 to 7 p.m. at Town Center Green, 600 Bay Isles Road. According to Longboat Key News, the Longboat Key Chamber of Commerce and the town organize it. The centerpiece is lighting the oak trees on the green, and the evening includes hot chocolate, cake and a visit from Santa. Longboat Key News also lists the Longboat Key Garden Club and Save Our Seabirds among the local groups taking part, and the event is free. The Longboat Observer's 2026 events roundup adds vendors, live music, food trucks and a costume contest.
The Chamber's listing shows where the decorations come from. Island businesses pay for them. Sponsorships for the "coastal holiday magic" that decorates the green come in at $75, $150 or $300, a music and sound sponsorship costs $300, and a vendor table costs $35. Those amounts are sized for a shop owner. A national sponsor would be spending far more. The lights over the green are paid for by the businesses along Gulf of Mexico Drive.
Nov. 29 Through Dec. 31: The Chapel Garden
Eight days later, the season moves north to Longboat Island Chapel at 6200 Gulf of Mexico Drive. A Town of Longboat Key memo prepared for the Nov. 2 commission meeting lists the chapel's Christmas in the Garden as running daily from Nov. 29 to Dec. 31, 2026, from 5 to 9 p.m. The town treats it as a community-wide event. The memo asks the commission to waive the $100 permit application fee, and staff recommended the waiver. Longboat Key News lists the event as free.
The garden is built the same way the green is decorated, by many local hands. Here is how the Longboat Observer described last season's display:
- Themed trees decorated by island businesses, organizations and residents
- Illuminated paths through the chapel garden
- Most of the displays assembled by volunteers
- Music from local performers and hot chocolate made by volunteers
The chapel first staged the event in 2021, and the Observer covered that opening season. The Chamber is also holding its Off the Clock networking event in the garden on Wednesday, Dec. 2, from 5 to 7 p.m.
Because the garden is open every night until New Year's Eve, it fits around the rest of the calendar. Any of the dated events below can be paired with a walk through the garden later in the evening.
The Dated Events Between the Two
These smaller events fall in the first half of December. Every one is organized by a local group, and most of them are free.
- Friday, Dec. 4: St. Armands Circle Holiday Night of Lights, 5:30 to 8:30 p.m. It features a 60-foot tree lighting, carols, dancers and Santa, according to the Observer's roundup.
- Sunday, Dec. 6: Hanukkah Open House at Temple Beth Israel, 567 Bay Isles Road. The Jewish Federation of Sarasota-Manatee's listing describes the temple's first Member Art Show, with congregants' art, Judaica and refreshments, plus a community candle lighting at 5:30 p.m. The event is listed as free.
- Thursday, Dec. 10: Holiday Floral Design with the Longboat Key Garden Club, 5:30 to 7:30 p.m. It takes place at the Bayfront Park Recreation Center. The Garden Club lists the cost as $85 for members and $100 for guests, with supplies and refreshments included.
- Saturday, Dec. 12: The 40th Sarasota Holiday Boat Parade. Suncoast Charities for Children and Marina Jack present it. It is free and open to the public, and the organizer points viewers to Bayfront Park and Marina Jack on the Sarasota side of the bay.
Two of these dates bring residents back to places that recently changed. The Dec. 10 floral night is at the town-run recreation center in Bayfront Park, 4052 Gulf of Mexico Drive. The pickleball and basketball courts in that park reopened on Oct. 23 after a $193,995 resurfacing project closed them over the summer, according to the Longboat Observer. Anyone arriving early can try the new surface before the class starts.
The boat parade has a Longboat Key connection too. Barefoot Tiki Tours, a member of the Longboat Key Chamber, is an official parade entry and is offering its whole boat for a private group that night. Boarding is at 5:30 p.m., and the outing runs until 8:30 p.m., per the Chamber listing. The same day, the Chamber calendar lists a wine tasting at LaNorma Ristorante & Pizzeria from 11:45 a.m. to 2 p.m.
Where Reservations and Prices Come In
The late-December events at the island's resorts are the main part of the season that comes with a price and a reservation requirement. The Longboat Key Club and Zota Beach Resort have both posted their 2026 holiday plans:
| Date | Event | Where | Price | Reservations |
|---|---|---|---|---|
| Dec. 24, 5 to 6 p.m. | Santa visit | Longboat Key Club lobby | Not listed | Not listed |
| Dec. 24, 6:15 to 7 p.m. | Carolers | The Tavern & Whiskey Bar, Longboat Key Club | Not listed | Not listed |
| Dec. 25, 10 a.m. to 3 p.m. | Christmas Day brunch | Viento Kitchen & Bar, Zota Beach Resort | $67 adult, $26 child 12 and under | Required |
| Dec. 25, seatings every 30 minutes, noon to 5:30 p.m. | Christmas dinner | Longboat Key Club | $120++ adult, $50++ child 5 to 12 | Required |
| Dec. 31, 9:30 p.m. to 1 a.m. | Adults-only New Year's Eve with food stations, open bar and Big Z Band | Longboat Key Club | $275+ per adult | Required |
Details are posted on the Longboat Key Club holiday page and Zota Beach Resort's holiday page. The Longboat Key Club's New Year's Eve party has a "Studio 54" theme.
Christmas in the Garden is scheduled through Dec. 31, so the garden paths stay lit until 9 p.m. on New Year's Eve, a half hour before the Longboat Key Club party begins. Times, prices and seatings can change in the weeks ahead, so check each organizer's page before you go.
The Season at a Glance
| Date | Event | Organizer | Cost |
|---|---|---|---|
| Nov. 21 | Light Up Longboat, Town Center Green | Longboat Key Chamber and the town | Free |
| Nov. 29 to Dec. 31, nightly | Christmas in the Garden | Longboat Island Chapel | Free |
| Dec. 2 | Off the Clock networking in the garden | Longboat Key Chamber | See listing |
| Dec. 4 | Holiday Night of Lights, St. Armands Circle | St. Armands Circle | See listing |
| Dec. 6 | Hanukkah Open House and Member Art Show | Temple Beth Israel | Free |
| Dec. 10 | Holiday Floral Design | Longboat Key Garden Club | $85 member, $100 guest |
| Dec. 12 | 40th Sarasota Holiday Boat Parade | Suncoast Charities for Children and Marina Jack | Free |
| Dec. 24 to 31 | Holiday dining and New Year's Eve | Longboat Key Club, Zota Beach Resort | By reservation |
For more on life around the island, see our Longboat Key neighborhood guide or our look at the north end's dining investments.
Ryan Miller grew up in Sarasota and keeps track of the island calendar all year, from the green on Bay Isles Road to the chapel at the north end. To get dates like these before each season starts, sign up for the newsletter.
