Lakes &
Live Oaks. 🌳
Orlando is built on water and shaded by ancient trees. The best dates here embrace the natural beauty of "Old Florida"—slow, scenic, and surprisingly lush.
The Swan Boats
Downtown
"It’s the definitive Orlando experience. Paddling out to the center of the lake gives you a stunning 360-degree view of the skyline. It’s quiet, private, and nostalgic."
💡 Date Tip
Go at sunset (around 7 PM). The fountain lights up in different colors, and the city buildings start to glow. It’s the most photogenic hour.
Lake Eola Park.
A sinkhole turned city jewel. The walking path is exactly 0.9 miles—perfect for a stroll with coffee in hand.
Farmer's Market
Every Sunday. It’s huge, loud, and full of food trucks. Grab a coconut, sit on the grass, and people-watch.
Dickson Azalea Park. 🌿
A historic park built *into* a ravine. The temperature drops noticeably as you descend the stairs. It feels like a secret tunnel hidden beneath the city streets.
Date Tip
Pack a thermos of coffee. There are quiet benches along the creek where the city noise completely disappears. It’s perfect for a morning date.
Washington St. Bridge
"The historic 1926 bridge arches high over the park. Looking up at the stone arch framed by ferns and towering trees gives the spot a moody, almost gothic romance."
Scenic Boat Tour. 🚤
An 18-passenger pontoon boat that cruises through the canals connecting the Winter Park chain of lakes. It’s charming, breezy, and historic.
Pro Move
Go for the 10:00 AM tour to beat the mid-day heat. Afterwards, walk two blocks to Park Avenue for brunch at The Briarpatch (get the raspberry lemon pancakes).
Venice of America
"The canals are narrow and lined with ferns and massive mansions. The guides tell terrible jokes, but that's part of the charm. It feels like stepping back into the 1920s."
The Dock
Lake Killarney
"Skip the dining room. The real move is to grab a glass of wine and snag two Adirondack chairs on the wooden dock. Watching the sun dip below the lake horizon here is an Orlando rite of passage."
💡 Date Tip
There is a dress code (no hats, no tank tops), and they enforce it. It keeps the vibe elevated and special.
Hillstone Winter Park.
It’s arguably the most famous sunset spot in the city. The sloping lawn, the fire pits, and the lake view create an atmosphere of relaxed luxury.
The Spinach Dip
Yes, it's just an appetizer, but it's legendary. Sharing it on the lawn with a cocktail is a perfect low-pressure date.
The Tiffany Chapel
Masterpiece
"Walk into the Byzantine-Romanesque chapel interior designed by Louis Comfort Tiffany for the 1893 World's Fair. It is a kaleidoscope of glass, mosaics, and light. It’s quiet, spiritual, and stunningly beautiful."
💡 Date Tip
On Friday nights from November to April, the museum offers free admission from 4pm–8pm. Combine it with a dinner reservation on Park Avenue.
The Morse Museum.
Home to the world's most comprehensive collection of works by Louis Comfort Tiffany. The jewelry, lamps, and leaded-glass windows create a warm, glowing atmosphere perfect for wandering.
Daffodil Terrace
Don't miss the reconstructed Daffodil Terrace. It’s an architectural gem where art and nature blend seamlessly.
The Exedra
Lake Maitland
"A secluded 5-acre park dominated by massive cypress trees. The centerpiece is the 'Exedra'—a towering semicircular stone monument framing the lake. It is arguably the most romantic sunset spot in the county."
💡 Date Tip
It’s a popular wedding spot, so if you see a ceremony, just loop around to the banyan trees on the south side. They are equally impressive and usually empty.
Kraft Azalea Garden.
Known locally as "The Secret Garden." It feels like a piece of ancient Greece dropped into a Florida swamp.
The Great Egrets
This is a nesting site for massive white herons. Watching them swoop between the Spanish moss at twilight is magical.
Camellia Forest
Audubon Park
"50 acres of tropical and semi-tropical gardens. The ancient oaks dripping with moss create natural canopies that feel private and secluded."
💡 Date Tip
Check their calendar for "Movie Night." You can bring a picnic blanket and a bottle of wine (alcohol is permitted during movies) and sit on the lawn under the stars.
Harry P. Leu Gardens.
A historic estate turned botanical wonderland. It’s quiet, expansive, and smells like jasmine and citrus.
Butterfly Garden
The most romantic spot in the park. It’s filled with nectar plants that attract hundreds of butterflies.
Wekiwa Springs. 🛶
Orlando's natural swimming pool. The water is a constant 72 degrees, crystal clear, and emerald green. Rent a double kayak and paddle upstream into the jungle.
Pro Move
The park hits capacity quickly on weekends. Go on a weekday morning or arrive by 8:00 AM. The silence of the river in the morning mist is worth the early wake-up.
Real Florida
"Forget the lazy river at the hotel. This is the real thing. You’ll see otters, turtles, and birds. It’s an adventure date that feels a million miles away from the theme parks."
Orlando Museum of Art. 🎨
Founded in 1924, OMA is the cultural anchor of the city. The architecture combines mid-century modern with contemporary glass, housing a fantastic collection of American and African art.
Date Tip
Visit during "1st Thursdays." It’s a monthly party from 6-9 PM with local artists, live music, and a cash bar. It turns a museum visit into a social event.
The Lawn
"The museum sits in Loch Haven Park, surrounded by massive, ancient oak trees including 'The Mayor' (one of the oldest oaks in Florida). It’s the perfect spot for a post-gallery walk."
Eden Bar
Under the Oaks
"The outdoor bar alone is a destination. Wrapped in 400-year-old live oaks and strung with lights, it is sultry, humid, and impossibly romantic. Sip a 'Gator Bite' cocktail before the show."
💡 Date Tip
You can order dinner and drinks *during* the movie. The theater has tables and servers. It’s dinner-and-a-movie, upgraded.
Enzian Theater. 🎬
Orlando's only alternative cinema. They screen independent, foreign, and classic films. It’s the hub of the Florida Film Festival and a haven for culture lovers.
Wednesday Night Pitcher Show
A free outdoor movie on the lawn every Wednesday. Bring a blanket/chairs. It’s casual, fun, and totally free.
The Library
Downtown Hideaway
"Hidden on the third floor of an antique furniture store building. You are greeted by a bookshelf that swings open. Inside, it’s 1920s glamour—leather sofas, brick walls, and swing music."
💡 Date Tip
Dress sharp. They have a strict "smart casual" dress code. Dressing up makes the date feel like a special occasion.
Mathers.
This isn't a club; it's a cocktail parlor. The bartenders are chemists, and the vibe is sophisticated.
Bathtub Gin
Try a cocktail served in a miniature bathtub. It’s gimmicky, but adorable and delicious.
The Foodie
Guide.
We are currently eating our way through the Mills 50 District (so many tacos and noodles) to bring you the definitive guide to Orlando's best food neighborhood.
Space Coast
Rocket Launch Viewing
Disney Springs
The Local's Guide
Mills 50
Asian & Tacos