Mark your calendars: tickets for the 13th annual Windermere Wine & Dine go on sale this Saturday at 9 a.m., and if history is any guide, they won't last long. The $175 tickets can be purchased at wochamber.com/windermere-wine-dine, giving buyers access to a night of unlimited tastings from dozens of Central Florida restaurants and wineries at the historic Windermere Town Hall on February 6, 2027.
The event, now carrying the tagline “Sip. Savor. Support.,” has become one of the hottest tickets in West Orange County, according to the West Orange Times & Observer. The West Orange Foundation is preparing next year's gathering, which will feature dozens of top-tier restaurants and premier wines at Windermere Town Hall, per the same report. Tickets have historically sold out within minutes of release, with recent editions capping attendance at roughly 700 guests, according to The Orlando Guy.
What's Included in the $175 Ticket
Admission covers unlimited tastings and a commemorative wine glass, with food samples from more than 30 Central Florida restaurants and over 100 wines, beers, and cordials on offer, The Orlando Guy reports. The scale of the spread has grown alongside the event's popularity, even as organizers keep the footprint anchored at Windermere Town Hall.
Longtime attendees Zach and Andi Stoumbos have only missed one Windermere Wine & Dine in the event's history. Zach Stoumbos said he and his wife keep coming back because of the people and the purpose of the funds, according to the Times & Observer.
A Grassroots Event Grows Into a Regional Fundraiser
The West Orange Foundation, the 501(c)(3) philanthropic arm of the West Orange Chamber of Commerce, officially took over leadership and hosting duties for Windermere Wine & Dine in October 2025, aiming to expand the event's reach while keeping its community roots intact, according to the Orange Observer. That shift moved an event founded by Windermere residents into the hands of a chamber-backed nonprofit with a much wider grant-making footprint.
The Foundation for a Healthier West Orange signed on as an official sponsor for the 13th annual event, the West Orange Chamber of Commerce announced earlier this month. The chamber's foundation disburses grant funding across 11 West Orange County municipalities and communities, including Windermere, Winter Garden, Dr. Phillips, Horizon West, and Ocoee, with a focus on priorities like food insecurity.
Where the Proceeds Go
Proceeds from past Wine & Dine events helped establish the Windermere Legacy Fund, a community grant-making nonprofit incorporated in 2025 that funds local charitable organizations including The Nurture Place. Chamber-backed philanthropic funds have also supported education locally, including $2,500 Danniel J. Petro Foundation Scholarships awarded to local high school graduates attending UCF, Valencia College, or Orange Technical College.
A Historic Backdrop for the Tastings
Windermere Town Hall, the centerpiece venue for the tasting event, was built in 1922 as a women's club, relocated to its current address at 520 Main Street in 1938, and listed on the U.S. National Register of Historic Places in June 1994, according to the National Park Service. The building's history adds a layer of small-town charm to an event that has otherwise outgrown its original scale.
During January's Windermere Wine & Dine, attendees queued outside Town Hall a half hour early in cold weather just to collect their wooden tasting trays and wine glasses, the Orange Observer reported at the time. With ticket demand only expected to climb for the 13th edition, organizers and longtime guests alike are bracing for another fast sellout when sales open Saturday morning.
