Orlando Date Spots

James Beard-nominated gastropub with on-site brewery

Wood-fired Italian on Park Avenue, Winter Park institution

Self-serve wine bar with 150+ wines via Enomatic machines

Downtown Orlando's heart — mile-long lake path, swan boats, fountain light show

Hidden lakeside garden with massive oak trees and the Exedra monument

Curated food hall in a restored citrus packing house

50-acre botanical garden on Lake Rowena with 1,000+ rose bushes

Spring-fed river kayaking through bald cypress corridors, 20 min from downtown

Tapas and sangria in a cozy Hannibal Square setting

Independent cinema with Eden Bar garden — indie films and craft cocktails

Boutique hotel with curated art collection, walkable to Park Avenue

Unmarked speakeasy — text for reservations, craft cocktails, 30 seats

Downtown rooftop bar with Lake Eola views and sunset cocktails

Modern American with rooftop seating on Park Avenue

Upscale casual with lake views, no reservations — arrive early

Craft cocktail pioneers — bartender-driven menu, quiet enough to talk

Western Orlando preserve — genuine darkness for stargazing, hiking trails

Art-themed luxury hotel downtown with rooftop bar

Full luxury resort with spa, citrus-infused treatments, Greg Norman golf

Hidden urban oasis near Thornton Park with massive oak canopy

Quieter alternative to Leu Gardens — free admission, butterfly garden

Narrated boat tour through Winter Park's chain of lakes — since 1938

Neighbourhood restaurant with craft cocktails and seasonal American menu

Alfond Inn's restaurant — seasonal farm-to-table done right

Local specialty roaster — multiple locations, great for low-key first dates

Southern comfort brunch institution — massive portions, incredible baked goods

Half-pound cookies with cult following — expect a line at Disney Springs

Full dessert bar, specialty coffee, open later than most Winter Park spots

Eclectic Thornton Park gem with live jazz brunch on Sundays

Tiki bar on the Wekiva River — swim, paddleboard, drink, sunset

Crystal-clear spring with winter manatee viewing from boardwalk

Stunning gardens with a 205-foot neo-Gothic singing tower — 1 hour south of Orlando

Immersive tiki bar at Disney's Polynesian — walk-in only, 30-seat capacity

Atlantic City-style boardwalk at sunset — no park ticket needed

Long-running LGBTQ+ club — drag shows, theme nights, inclusive community

Drag brunch and dinner shows — interactive, inclusive, great first date energy

Best tacos in Orlando — casual, cheap, BYOB

Neighbourhood wine bar in Thornton Park — cheese boards, relaxed vibe

Crystal-clear spring-fed lazy river tubing run — arrive early, sells out

Franchise but well-executed couples treatment rooms in Colonial Plaza

Production-quality escape rooms — locally owned, cinematic sets

Spanish gastrobar with shareable plates and buzzy atmosphere

Park Avenue classic since 1980 — outdoor seating under live oaks

11-mile drive-through birding trail — golden hour is spectacular

Small art museum on the lake — $5, uncrowded, sculpture garden

Free art museum at Rollins College — rotating exhibitions, lakefront campus

Victorian-era lounge with dress code — Wall Street Plaza's classy secret

French brasserie downtown — soaring ceilings, prix fixe brunch deal

Southern-inflected restaurant with a patio overlooking Lake Eola

Elevated comfort food in a converted Craftsman bungalow with coveted porch seating

AAA Five Diamond, 7-10 course prix fixe — Central Florida's most acclaimed restaurant

Indiana Jones-themed hangar bar at Disney Springs with craft cocktails and waterfront seating

20-seat omakase counter — some of the best sushi in the Southeast

Dessert-only restaurant with elaborate sweets, cocktail pairings, and red velvet atmosphere

Turkish restaurant with house-made baklava, kunefe, and Turkish coffee worth a dedicated visit

Hidden speakeasy with mismatched furniture and off-menu cocktails — a wealthy eccentric's living room

Rooftop bar and restaurant with direct Lake Eola fountain views and live music nights

Upscale Latin tapas with a rooftop lounge — passion fruit mojitos and patatas bravas

Vintage-barbershop cocktail den with tableside smoked old fashioneds

Over 100 mezcals and contemporary Mexican food — the mole negro alone is worth the trip

Sunrise hot air balloon flights over Kissimmee with champagne toast on landing

Couples pottery wheel-throwing workshops — make something together and pick it up two weeks later

Sensory deprivation float tanks — 1,000 lbs of Epsom salt, complete darkness, profound relaxation