Windermere Wine & Dine 2027 Tickets | Feb 6 Date, Time & Location
Windermere Wine & Dine 2027: Date, Tickets, Location, and What to Expect
Windermere Wine & Dine is Central Florida’s most anticipated annual food and wine tasting event. Held in the heart of the Town of Windermere, this sold-out evening brings together dozens of top restaurants, premier wineries, live music, and neighbors who want to give back. The 2027 event takes place Saturday, February 6, 2027, at Windermere Town Hall and Town Square Park.
The official tagline says it best: Sip. Savor. Support.
2027 Windermere Wine & Dine Event Details
- Date: Saturday, February 6, 2027
- Time: 6:00 PM (historically runs until 9:00 PM)
- Location: Windermere Town Hall and Town Square Park
- Address: 520 Main Street, Windermere, FL 34786
- Ticket Price: $175 per person
- Ticket Sales Begin: Saturday, October 24, 2026
Tickets sell out quickly every year. In recent editions only about 700 tickets were released, and they disappeared within minutes. Anyone hoping to attend the 2027 Windermere Wine & Dine should mark October 24, 2026 on the calendar and sign up for notifications on the official West Orange Chamber page.
What Is Windermere Wine & Dine?
Windermere Wine & Dine is an outdoor tasting event under the stars. Guests move between stations set up around Town Square Park, sampling gourmet bites from more than 30 Central Florida restaurants and tasting more than 100 wines, beers, and cordials. Each ticket includes a commemorative wine glass and unlimited tastings.
The event is now hosted by the West Orange Foundation, the philanthropic arm of the West Orange Chamber of Commerce. It was founded more than a decade ago by civic-minded Windermere residents who wanted to raise money for local causes. That community-first spirit remains the core of the evening.
Participating restaurants have included names such as The Ravenous Pig, Cask & Larder, Ocean Prime, Capital Grille, Stonewood Grill, Dexter’s, Pilars, and many others. The exact 2027 lineup will be announced closer to the date, but organizers typically contract 30-plus restaurants, with a wait list for additional vendors.
What’s Included With Your Ticket
A $175 ticket typically includes:
- Unlimited food tastings from 30+ restaurants and caterers
- Tastings of more than 100 wines plus beer and cordials
- A keepsake commemorative wine glass
- Live music throughout the evening
- High-top tables and an elegant outdoor setting in the center of town
- The chance to connect with neighbors, local leaders, and fellow supporters
Dress is elevated casual. Comfortable shoes are recommended because guests spend the evening walking between stations. Non-drinkers are welcome; food stations and non-alcoholic options are available.
Community Impact: More Than $2 Million Raised
Every ticket purchased supports the West Orange Foundation and the Windermere Legacy Fund. Over the event’s history, Windermere Wine & Dine has helped fund more than $2 million in grants for:
- Educational opportunities and scholarships for local students
- Food insecurity programs
- Health and wellness initiatives
- Economic empowerment programs
- Community revitalization efforts
The 2025 event alone generated more than $200,000 for local charities. A portion of proceeds now flows to the Windermere Legacy Fund, which awards grants that keep dollars and volunteer energy inside the Windermere community while also encouraging broader civic engagement.
History of Windermere Wine & Dine
The event began as a grassroots effort by a small group of Windermere parents. The first Wine & Dine featured 13 restaurants and raised $35,000. It quickly became an annual tradition. Attendance grew past 1,000 guests in some years, tickets began selling out in minutes, and the event evolved from a local fundraiser into one of West Orange County’s signature nights.
In 2025–2026 the original volunteer organizers transferred leadership to the West Orange Foundation so the event could scale while preserving its community character. The Foundation now handles operations, sponsorships, and grant distribution while keeping the same high-end, neighborly atmosphere that made the event famous.
How to Get 2027 Windermere Wine & Dine Tickets
Tickets for the February 6, 2027 event go on sale Saturday, October 24, 2026. The price is $175. Sales are handled through Ticket Tailor via the official West Orange Chamber website.
Because demand far exceeds supply, the best strategy is to:
- Visit wochamber.com/windermere-wine-dine and use the “Notify Me” option.
- Set a reminder for the morning of October 24, 2026.
- Be ready to purchase immediately when sales open.
Tables and group options have been offered in past years; details for 2027 will be released with ticket information.
Practical Tips for Attending
- Arrive early. Lines form before the official 6:00 PM start.
- Wear stylish but comfortable clothing and shoes suitable for standing and walking on pavement and grass.
- Bring an appetite. Stations are generous and variety is high.
- Parking is limited in downtown Windermere; plan extra time or consider rideshare.
- The event is outdoors. Check the weather and dress in layers if a cool February evening is forecast.
- The event is 21+ for alcohol service.
Why Windermere Wine & Dine Sells Out Every Year
Few events combine this level of culinary quality, convenient location, and clear community purpose. Guests leave with full glasses, full plates, and the knowledge that their ticket funded scholarships, food programs, and neighborhood projects. That combination—great food, great wine, and a genuine local mission—has made Windermere Wine & Dine the must-attend winter event in West Orange County.
Mark your calendar: Saturday, February 6, 2027, 6:00 PM, Windermere Town Hall, 520 Main Street. Tickets go on sale October 24, 2026. Sip. Savor. Support.