The Wine Room on Park Avenue to Toast 20 Years With Weeklong Celebration of Sips, Stories and Spectacular Vintages

For two decades, The Wine Room on Park Avenue has been more than just a place to grab a glass of something special. It’s been a date-night staple, a girls’ night headquarters, a connoisseur’s playground, and, for many Central Floridians, a gateway into the world of wine. Now, the beloved Winter Park institution is raising a glass to 20 years with a weeklong anniversary celebration packed with tastings, winemaker meet-and-greets, giveaways and signature experiences that reflect the venue’s one-of-a-kind spirit.

Starting Saturday, January 31, the milestone celebration will unfold over seven days of free and ticketed events, inviting longtime fans and newcomers alike to sip their way through The Wine Room’s past, present and future.

“Our venue is known in Orlando and around the country as the place to enjoy the greatest wine experience anywhere,” founder and owner Bruce Simberg said. “We are pleased to share our 20th anniversary celebration with a wine community of over one million guests who have supported us since 2006.”

A Party That Pours On

The festivities begin Saturday, January 31, with a ticketed Vault Wine & Cheese Tasting Event featuring Silver Oak Winery, from 6:30 to 8:30 p.m. Held inside The Vault, a 75-year-old former bank vault turned intimate tasting room, the experience sets the tone for what’s to come: elevated, immersive and just a little magical.

Sunday, February 1, brings a double dose of celebration. From 1 to 3 p.m., The Wine Room will host its official 20th Birthday Party, complete with free wine and food samples. Later that evening, guests can attend a complimentary meet-the-winemaker event with Alberto Scarani of Italy’s Ca’ Montebello, from 5 to 7 p.m.

Monday, February 2, keeps the momentum flowing with another Vault Wine & Cheese Tasting, this one led by Max McCalman, Maître Fromager and one of the most respected cheese experts in the country. That same day, The Wine Room will roll out its popular Match It Monday wine card promotion from 2 p.m. to midnight, offering guests even more reason to linger.

On Tuesday, February 3, the Vault hosts a tasting themed “Our Favorites From the Last 20 Years,” highlighting standout wines that have defined The Wine Room’s history. Wednesday, Feb. 4, brings the venue’s beloved Ladies Night from 4 p.m. to close, while Thursday, February 5, offers perhaps the most personal experience of the week: a Vault tasting straight from Simberg’s own cellar, featuring curated 2006 vintage wines.

The celebration culminates Friday, February 6, The Wine Room’s official anniversary, with hourly raffle giveaways and a full day of festivities.

For tickets and more information call 407-696-WINE (9463).

A Concept That Changed How Orlando Drinks Wine

When The Wine Room opened its doors in 2006, it introduced something entirely new to Central Florida: a self-pour wine experience that felt both sophisticated and approachable.

Simberg and co-founder Misti Greene envisioned a space that broke down the intimidation factor of wine, allowing guests to explore at their own pace. The heart of that vision remains today in the form of 156 self-service Enomatic wine dispensers, each holding hand-selected bottles from around the world. With the swipe of a card, guests can sample, sip or savor full pours—no sommelier pressure required.

That interactive approach, combined with a warm, European-inspired ambiance, helped The Wine Room quickly establish itself as a Park Avenue fixture.

Over the years, the concept expanded beyond wine. Flatbreads, small plates and tapas-style offerings turned casual tastings into full evenings out. The retail selection grew, earning Wine Spectator’s “Best of Award of Excellence” year after year. Online shopping, delivery and private events followed.

And then there’s The Vault.

Once a functioning bank vault, the subterranean space has been transformed into one of the most unique private tasting rooms in the region. Its thick steel doors and softly lit interior create an atmosphere that feels equal parts secret club and Old World wine cellar—an experience that regulars often describe as unforgettable.

Awards, Accolades and a Loyal Following

The Wine Room’s resume reads like a greatest-hits list of Orlando dining honors. It has won the TripAdvisor Travelers’ Choice Award, been named Orlando Weekly’s “Best Wine Bar” 12 times, and received Orlando magazine’s “Best Wine Bar” title on multiple occasions.

But Simberg says it’s the loyalty of the community that matters most.

“We’ve always believed in pleasing every palate at every price point,” he said.

That philosophy is reflected not only in the wine dispensers—featuring selections from Europe, South America, California and beyond, but also in the cheese department, which sources varieties from around the world for guests to enjoy on-site or take home.

“The Wine Room is a completely immersive wine experience with a wine bar that evokes an exclusive chateau while you taste a global selection of wines and cheeses, or a whole tapas-style meal,” Simberg said. “We look forward to sharing that experience with even more wine lovers in the next 20 years.”

A Place That Grows With Its Guests

Ask any longtime patron, and they’ll likely tell you their own Wine Room story: first dates that turned into anniversaries, casual happy hours that became weekly traditions, spontaneous tastings that sparked lifelong wine obsessions.

That emotional connection is part of what makes the 20th anniversary feel less like a business milestone and more like a community celebration.

The upcoming lineup reflects that spirit, blending education, indulgence and pure fun. From winemaker meet-and-greets to vintage tastings, from raffles to free samples, the events are designed to welcome everyone—from novices to collectors.

It’s a fitting tribute to a venue that has always believed wine should be enjoyed, not fussed over.

Looking Ahead

As The Wine Room steps into its third decade, Simberg remains focused on innovation while honoring what made the concept successful in the first place.

“The heart of The Wine Room has always been exploration,” he said. “Trying something new, learning what you love, sharing that experience with friends.”

If the packed anniversary calendar is any indication, the next 20 years will be just as vibrant.

About The Wine Room on Park Avenue

The Wine Room on Park Avenue in Winter Park, Florida, first opened its doors Feb. 6, 2006. A unique concept combining a retail wine and cheese shop with a restaurant and wine bar, The Wine Room showcases 156 hand-selected wines from around the world, available via state-of-the-art Enomatic wine dispensing machines. All wines are also available for purchase. The Wine Room’s wine selection has received Wine Spectator’s “Best of Award of Excellence” 13 years in a row.

For more information, visit their website or call 407-696-WINE (9463).