Hannibal Square


Today I decided to leave my usual zoom lenses at home and spend some time walking Hannibal Square with nothing more than a 35mm lens. Sometimes a single focal length forces you to slow down, observe, and appreciate a place for what it is rather than what you can make it look like. That mindset turned out to be the perfect match for Hannibal Square.


Most visitors immediately think of Park Avenue when they think of Winter Park. Park Avenue certainly deserves its reputation, with its boutiques, cafés, and constant activity. But after spending time wandering Hannibal Square, I was reminded that this is where Winter Park feels most authentic.

Tree-lined urban sidewalk with parked cars, historic building facades, and blue awnings in a charming Southern city street scene.
Historic corner building with wrought iron balcony, brick sidewalk, street lamp, and lush trees in a charming Southern downtown district.
Tree-lined historic downtown street with parked cars, iron bench, brick sidewalk, and vintage archway sign in warm sepia tones.
Historic building with ornate wrought iron balconies, wooden columns, and yellow stucco walls surrounded by lush trees.
White MINI Cooper Countryman parked on brick street beside lamppost with historic brick buildings and trees in urban setting.
Aeffect Hair salon entrance with elegant awning at Suite 100, framed by brick walls and lush trees.
Cozy cafe interior with ornate hanging pendant lights, a menu board, and a bright window view of trees outside.
Charming storefront with a bright yellow door, black awning, and decorative ironwork on a white brick building.
Charming outdoor sidewalk cafe with a chalkboard brunch sign, string lights, and lush trees lining a quaint downtown street.
Historic brick building at 444 The Plaza with street-level awning entrance, lined with parked cars and lush trees.
Ivy-covered brick restaurant facade with striped awnings and outdoor cafe seating on a charming urban sidewalk.
Historic brick building with arched gateway, tree-lined cobblestone street, and outdoor cafe seating in a charming Southern town square.
Silver Nissan Rogue SUV parked outside The Palms at Hannibal Square boutique in a scenic Southern town with Spanish moss trees.
Quaint storefront with dark awnings, outdoor seating, and lush trees on a sunny urban street corner.

Most visitors immediately think of Park Avenue when they think of Winter Park. Park Avenue certainly deserves its reputation, with its boutiques, cafés, and constant activity. But after spending time wandering Hannibal Square, I was reminded that this is where Winter Park feels most authentic.


Located just a few blocks west of Park Avenue, Hannibal Square carries a rich history that predates much of what visitors associate with modern Winter Park. Founded in 1881, it became the center of Winter Park’s African-American community and played a significant role in the city’s development. Today, that heritage is preserved through the Hannibal Square Heritage Center, which documents the stories, photographs, and contributions of generations who helped build the city.


What makes Hannibal Square special is its pace.


Unlike Park Avenue’s constant flow of shoppers and tourists, Hannibal Square feels relaxed. The sidewalks are quieter. Conversations seem to last longer. The restaurants and galleries feel more connected to the neighborhood than to a destination shopping district. It is the kind of place where a photographer with a 35mm lens can simply wander and discover scenes rather than chase them.


For many years, one of the anchors of the district was Chez Vincent.


For me, Chez Vincent was more than just a restaurant. It was arguably the finest French dining experience in Central Florida. Hidden away from the crowds, it delivered authentic French cuisine and hospitality that felt transported directly from a small European town rather than a suburban Orlando neighborhood.


Sadly, that chapter has come to an end.


After 28 years in Hannibal Square, Chef Vincent Gagliano and his family announced their retirement and the closure of both Chez Vincent and Hannibal’s Lounge. The restaurant served its final meals in December 2025, ending nearly three decades as one of Winter Park’s most beloved dining institutions. The family sold the business as they prepared to step into retirement.  


The loss of Chez Vincent feels symbolic in many ways. It represents the passing of an era when some of Central Florida’s best experiences weren’t heavily advertised, weren’t trending on social media, and weren’t packed with crowds every night. You simply had to know they were there.


The good news is that the space will continue its culinary legacy, with a new concept called The Reverie planned for the historic location. Still, for longtime visitors, there will only ever be one Chez Vincent.  


As I walked the neighborhood today, camera in hand, I couldn’t help but think that Hannibal Square and Chez Vincent shared something in common: both were quietly exceptional.


Neither needed the spotlight.


Perhaps that’s why Hannibal Square remains one of the most underrated areas in Central Florida. It doesn’t compete with Park Avenue. It complements it. One offers energy and activity; the other offers character, history, and the opportunity to slow down.


And sometimes, slowing down is exactly what both photography and travel are supposed to be about.


If you’re visiting Winter Park, by all means stroll Park Avenue. But then take the extra five-minute walk west. Bring a camera. Leave the itinerary behind. Wander the brick sidewalks of Hannibal Square.


You might just discover the side of Winter Park that many people overlook—and in doing so, find the side that’s most worth remembering.