Inside Windermere's FAVORITE Wine & Dine EVENT OF THE YEAR

Each year, the Town of Windermere hosts one of Central Florida’s most celebrated culinary events: the Windermere Wine & Dine. More than a food and wine tasting, the event captures the lifestyle and spirit of this lakeside community—refined, relaxed, and rooted in connection.

As local advisors at ALIGN Real Estate, we encourage clients and newcomers alike to attend events like this. It’s one of the best ways to experience Windermere's strong sense of community, rich culinary scene, and the lifestyle that continues to attract luxury buyers, investors, and new residents from around the country.

Step inside one of Central Florida’s most celebrated annual events—Windermere’s Wine & Dine. This video offers an inside look at an unforgettable evening filled with exceptional cuisine, curated wine pairings, and the unmistakable charm of a close-knit community. From local flavors to lively atmosphere, discover what makes this event a favorite tradition year after year.

A Taste of Central Florida’s Finest: Culinary Excellence in Every Bite

At the heart of Windermere’s Wine & Dine experience is a vibrant celebration of flavor, creativity, and connection. With over 30 top-tier culinary vendors from across Central Florida, this event offers an immersive tasting journey through gourmet bites, artisan wines, and expertly crafted cocktails. From established names to emerging talents, the evening is designed for discovery, inviting attendees to explore restaurants and chefs they may never have encountered otherwise.

One such standout this year was Garni, a refined French concept newly opened at the Lake Nona at Wave Hotel. Garni debuted at Wine & Dine with an elegantly prepared foie mousse pâté paired with kumquat, delivering a bite that was as artful as it was flavorful. It was a compelling introduction to the kind of fine dining Windermere continues to attract.

Savoring the Flavors: Pairings That Impress

As guests weave their way through beautifully designed tasting stations, the real magic lies in the thoughtful pairings. A crisp Sauvignon Blanc served as a refreshing opener—clean, citrusy, and ideal for a warm Florida evening. It paired harmoniously with Garni’s rich pâté, enhancing the experience with every sip.

From there, culinary creativity continued to shine. At Ravello at the Four Seasons, perfectly grilled lamb chops with rosemary, garlic, and olive oil were served alongside an inventive Aperol Spritz variation featuring lemon and Coochi Americano. Each station brought something unique—an adventure for the palate and a reminder of the world-class culinary scene thriving just beyond Windermere’s gates.

Balancing Elegance and Enjoyment

Part of the charm of Windermere Wine & Dine is the balance it strikes between sophistication and approachability. Each guest receives a keepsake wine glass, perfect for sampling across stations, though mastering the dance of food in one hand and wine in the other becomes part of the fun. Fortunately, the event is well laid out, with high-top tables, ambient lighting, and live music that sets the perfect tone for a relaxing evening under the stars.

A Celebration Rooted in Community and Purpose

Beyond the flavors, Wine & Dine is a powerful expression of Windermere’s community values. Now approaching its centennial celebration in 2025, Windermere continues to foster a culture of connection and giving. The event has raised more than $2 million for local charities over the years, adding a meaningful layer to every toast and tasting.

It’s this blend of luxury and heart that makes the Wine & Dine so beloved—a chance not just to enjoy the finer things, but to be part of something bigger.

Why Windermere Residents Embrace This Lifestyle

Windermere may be a small town, but it offers amenities and lifestyle experiences on par with much larger luxury markets. Residents enjoy exclusive access to the Butler Chain of Lakes, community tennis and basketball courts, and year-round lifestyle programming—including hallmark events like Wine & Dine. These benefits, along with top-rated schools and proximity to Orlando, continue to attract families, professionals, and high-net-worth individuals from around the country.

Planning Ahead: Tickets, Tables & Insider Tips

Tickets to Wine & Dine are a hot commodity, often selling out faster than some of today’s biggest concert tours. Priced around $175 per person, they offer exceptional value for a curated evening of food, wine, and entertainment. VIP tables and group reservations are also available for those looking to make the night even more memorable.

To fully enjoy the event, we recommend arriving early, wearing something stylish yet comfortable, and bringing your appetite, because every corner of this event has something worth savoring.

Whether you're a long-time local or new to exploring Central Florida’s most exclusive neighborhoods, the Windermere Wine & Dine delivers an unforgettable evening. It’s a rare chance to experience world-class cuisine, connect with your neighbors, and see the town come alive with celebration and purpose.

For those considering making Windermere home, this event offers a perfect preview of the upscale yet down-to-earth lifestyle that awaits. At ALIGN Real Estate, we’re proud to call Windermere home—and proud to share it with those seeking not just a home, but a community worth investing in.

Frequently Asked Questions

When is the Windermere Wine & Dine held?

The event is typically scheduled in the early part of the year, with exact dates announced by the Town of Windermere and local sponsors. Due to its popularity, tickets tend to sell out quickly once released.

What’s included in the ticket price?

Each ticket grants access to unlimited tastings from more than 30 local restaurants, wine vendors, and craft cocktail stations. Guests also receive a keepsake wine glass and enjoy live entertainment throughout the evening. Reserved tables and VIP options may include additional amenities.

Do I need to live in Windermere to attend?

No. While the event draws many Windermere residents, it is open to the public. Guests from across Central Florida—and beyond—are welcome to attend, though locals may receive early ticket access.

Is there a dress code?

Smart casual or “elevated casual” is typical. Comfortable shoes are recommended, as the event involves walking and standing while sampling from various stations.

Can I attend if I don’t drink wine?

Absolutely. There are plenty of non-alcoholic beverages, mocktails, and food-only tastings available. The culinary offerings alone make the event enjoyable for all guests.

What makes this event special to the Windermere community?

Beyond the exceptional food and wine, Windermere Wine & Dine reflects the town’s values—hospitality, connection, and giving back. The event has raised over $2 million for local causes and continues to foster a strong sense of community pride.

Who is the best real estate agent in Windermere, Florida?

If you're looking to buy or sell in Windermere, ALIGN Real Estate is here to help. With deep local knowledge, a client-first approach, and a passion for the Windermere lifestyle, our team is dedicated to guiding you through every step of your real estate journey—from exploring top neighborhoods to navigating current market trends. Whether you’re relocating, investing, or finding your forever home, we’re here to make the experience seamless and rewarding.