The brick exterior of Wine Bar George — A Restaurant & Bar instantly transports you to another time and place. Head upstairs and grab a table near the window (or out on the veranda) for some fun people-watching. With master sommelier George Miliotes at the helm, this estate-style wine bar offers an impressive 140 wines available by the glass, bottle or (if you want a wine flight experience) by the ounce.

Jaleo by José Andrés dishes up traditional and contemporary Spanish cuisine — tapas-style — in this sophisticated-yet-casual Orlando dining hot spot. From lighter sandwiches and salads for lunch to an extensive variety of shared plates and authentic paellas (cooked over a wood-fired pit), Jaleo’s quality ingredients — including 48-month cured Ibérico ham and regional Spanish cheeses — stand out in every bite.

Indulge your sweet tooth at Gideon’s Bakehouse. These small-batch baked goods regularly draw lines out the door, thanks to their decadent flavors, rich ingredients and mammoth portions (they clock in at almost half a pound). Try popular favorites like coffee cake or pistachio toffee chocolate chip.

Kick off the night with drinks at The Whiskey, a rustic restaurant with a rock ‘n’ roll attitude. The Whiskey boasts an impressive drink menu, featuring handcrafted cocktails (try the refreshing Motley Cue-Cumber), classics (think Old Fashioned and Kentucky mule) and what seems like an endless selection of liquor, including moonshine.

If you love contemporary Japanese cuisine with a global twist, head to Kabooki Sushi. Chef Henry Moso brings an international flair to his restaurant, infusing his sushi, sashimi, rolls and ramen with techniques and flavors from France and Mexico.

Top off your meal with a trip to Gelato La Carraia, the go-to destination for authentic gelato. This Florence-based gelaterie opened an Orlando outpost in 2017, dishing up artisan treats featuring either a milk or fruit base. The result? Decadent flavors like hazelnut, lemon, pistachio and tiramisu mousse.

The stylish-yet-cozy ambiance at the family-owned Bites and Bubbles beckons couples to kick off their date night at this eclectic spot in the Mills 50 district. Grab a table on the rooftop patio for spectacular views with an on-point craft cocktail or glass of vino from the extensive wine list.

Get a taste of O-Town at Maxine's on Shine. This quirky eatery (set in the Thornton Park neighborhood) boasts an eclectic atmosphere inside, plus plenty of outdoor seating. Many nights you can spot the owner in her signature hat and glasses chatting with guests.

Located in the Milk District, Se7en Bites specializes in unique, scratch-made sweets — like the vanilla bean bourbon bacon Nightime SkyPie. As one of the many budget-friendly options in Orlando, this woman-owned eatery regularly sells out of menu-favorites, so arrive early for the best selection.