Hannibal Square Date Night Ideas

Just minutes from Winter Park’s famed Park Avenue, Hannibal Square boasts many of the same charms in a more compact form with a quieter atmosphere. Romantic restaurants line the brick streets, boutiques and museums beckon you inside, and lengthy happy hours make dates budget-friendly. You’ll find most of the action concentrated along W New England Ave between S Pennsylvania Ave and Virginia Ave. Here are a few of our favorite restaurants for date night in this charming square.

Updated March 2024 by Meghan Roth

Restaurants with a Romantic Vibe

Vinia Wine Bar

444 W New England Ave

Since opening in late 2018, Vinia Wine Bar has developed a loyal following of regulars coming from near and far. Owned by husband and wife team Paula and Fabio, the cozy space oozes charm and class. Work from local artists lines the walls, candles dot every table, and the backlit bar is the perfect place to meet new friends. The wine list features primarily European wines from France, Italy, and Spain (I love the Cortese). There are also frequent wine dinners and tastings, plus live music select nights.

Savory dishes from Chef Ronnie Vance complement the curated wine list. Bite into the succulent Vinia surf & turf (slow braised brisket and roasted prawns) or melt-in-your-mouth Pancetta al Forno (roasted pork belly served with burnt onions and cantaloupe). Don’t skip dessert—the dessert flight allows you to try small portions of all three desserts for just $10.

Pancetta al Forno | Image credit: Stephanie Patterson


463 W New England Ave

Armando’s is ideal for a romantic date night. There’s a large and lively indoor dining area, and a more toned-down outdoor patio. The menu is comprised of classic Italian favorites plus unique Armando’s specialties. We highly recommend trying one of their handcrafted pizzas—our favorites are the San Giovanni (mushrooms, mozzarella, truffle oil, fried eggs) and the Prosciutto E Fichi (mozzarella, gorgonzola, prosciutto, fig jam). Armando’s also offers a great brunch menu on weekends, and a weekly happy hour at the bar with $2-$5 drink specials.

Chez Vincent & Hannibal’s on the Square

533 and 511 W New England Ave
chezvincent.com; hannibalslounge.com

Owned by Chef/Owner Vincent Gagliano and his wife, Teri Gagliano, Chez Vincent and Hannibal’s on the Square are date night staples in Hannibal Square. The former has been in business for more than 20 years, specializing in traditional French cuisine served in an upscale setting. Next door, you’ll find Hannibal’s on the Square, a trendy lounge with live music on the weekends, a spacious bar, and intimate dining. The menu focuses on classic French cuisine and global wines. The real stunner is the underground wine cellar, available for private dinners and events.

The wine cellar at Hannibal's on the Square

Casual Cuisine for a Chill Night Out

Park Avenue Tavern

558 New England Ave

Founded in NYC in 2010, Park Avenue Tavern is the quintessential American bar and restaurant, centered around a combination of classic elegance and over the top hospitality. Located in the heart of Winter Park, FL, the second location of Park Avenue Tavern serves lunch, dinner, weekend brunch, and a full beverage menu with martinis and cocktails, wine, and cold beer.

The center bar is the focal point to a vibrant dining and bar scene enhanced by the large windows providing expansive views. Cozy up in a booth accented by comfy leather seating and warm lighting.

Craving a burger? PAT is known for the best burger! Order the Park Burger with melty cheese, caramelized onions, and special sauce or the Tavern Burger with savory gorgonzola and red onion. Other favorites include the Spinach & Artichoke Dip and Burrata, perfect for a snack or appetizer to start the meal. Really hungry?  Try the Guinness Battered Fish & Chips or PAT’s Roasted Chicken. Don’t forget to end your dining experience with a Chocolate Chip Cookie Skillet, served warm, straight from the oven with vanilla gelato.

Pepe’s Cantina

433 W New England Ave

The food, the drinks, and the upbeat atmosphere make Pepe’s Cantina a real Winter Park gem. They offer an extensive menu of classic Tex-Mex cuisine, plus fun and innovative twists on the favorites you know and love. Pepe’s is a great place for vegetarians and vegans, as they offer multiple veggie-centric selections plus vegan cheese and Beyond Meat. No matter when you go, you’re sure to find a great drink deal at their adorable outdoor bar.

They offer happy hour Monday through Friday from 11:30am-5pm. Happy hour includes $5.75 house margaritas, sangria, well liquors, and Pepe's Lager.

If you miss happy hour, there are specials almost every day, which include:

  • Margarita Monday: $5.75 house margaritas
  • Taco Tuesday: 3 baby tacos for $7.99
  • Pitcher Wednesdays: Grab a pitcher of sangria, house margarita, or draft beer for $19.99 all day
  • Sunday Funday: Brunch and bottomless mimosas, sangria, and Pepe's Lager from 11:30am-3:00pm
Pepe's Cantina | Image credit: Stephanie Patterson

JAM Hot Chicken

400 W New England Ave

JAM Hot Chicken was born through through odd jobs, culinary awakenings, a handful of pop-ups, some freakin’ awesome people, and one finely tuned, supremely simple, hot chicken sandwich.

You could say this little chicken shack is a dream come true — from a food cart pop-up to settling into a place that has always been home to the owners. They’re an Orlando food joint that does two things right: hot chicken and good vibes.

Mynt Fine Indian Cuisine

535 W New England Ave

One thing to love about Hannibal Square, and Winter Park in general, is the diversity of global cuisine available at every corner. A favorite among date nighters (and a past runner-up for Best Indian in Orlando Sentinel Foodie Awards), Mynt is a go-to for authentic and artfully presented Indian cuisine in an upscale setting. There are a few outdoor tables for dining al fresco. 

Image credit: Mynt

CFS Coffee

430 W New England Ave

Located next door to Sausage Shack, CFS Coffee (short for Café Frutos Selectos) is a warm and inviting place to savor coffee or linger over a light meal. In addition to Colombian coffee, CFS also serves tea, wine, beer, sangria, salads, smoothie bowls, toast, sandwiches, pastries and more. The highlight of the Winter Park location is the picturesque corner seating area, complete with decorative pillows, eclectic art on the walls, and a coffee table. If a world nomad decided to open a local coffee shop, I imagine it would look a lot like CFS.

Image credit: CFS Coffee

Explore Free Things to Do…

You don’t need to spend a dime to visit this charming corner of Winter Park. For a totally free date, start the day perusing the local shops, like Rifle Paper Co. Inside you’ll find an assortment of colorful paper goods, like art prints, stationary, planners and more.

Pause for a picnic in Shady Park, a small but scenic city park with paved walkways, picnic tables, benches, and plenty of green space. Bring along your own provisions or pick up budget bites from the aforementioned Sausage Shack.

Lastly, plan a visit to the Hannibal Square Heritage Center. This free museum, opened by the Crealdé School of Art, is an ode to the area’s African American community and history. Inside you’ll find an impressive permanent exhibition, which includes oral histories and photographs from the community, plus traveling art exhibits. For a more in depth experience, join the monthly Hannibal Square walking tour led by Chief Historian Fairolyn Livingston (3rd Saturday of each month from 10-11:30am). The museum also hosts an annual Folk and Urban Art Festival in April.