Do date night right in Orlando, whoever you are. If you're new to town, it's hard to know how to plan out the ideal agenda for maximum (or minimum?) hookup potential. Our editors put together three very different dates, for three very different (hypothetical) couples.
Date No. 1:
Caffeinate ... somewhere
We love a daytime date, but if you're in it for a long haul, you'll need to stay peppy. Orlando absolutely abounds in excellent coffee houses — Deeply and Craft & Common downtown; Lineage in Mills 50 and Audubon Park; New General and Kos in Winter Park; Easy Luck in the Milk District — so your choice may depend on what's the most convenient to your respective starting points. For the purposes of this guide let's pick Framework Craft Coffee House for its proximity to our next stop. Framework (1201 N. Mills Ave.) offers creative coffee drinks like smoked Thai tea, macadamia matcha latte and the "baklavatte," a latte with honey and a toothpicked baklava garnish.
Look at cool stuff at Orlando Museum of Art
Orlando's flagship art museum is the Orlando Museum of Art (2416 N. Mills Ave.), and if it's summer, then OMA's Florida Prize in Contemporary Art exhibition is up. This annual show brings together the best and brightest of Florida artists working today, and takes over the museum's galleries with a trove of exciting and challenging work. If this is a first (or early-on) date, reactions to/comments on art are always a great way to learn about someone new.
Eat something at the Strand
Now it's time to have a bite to eat, a glass of wine, and a deeper dissection of what you just saw. Or go for it and grab the third rail: Bring up the nitty-gritty stuff like politics, religion, and dairy versus oat milk. Staying in the Mills 50 corridor, the Strand (807 N. Mills Ave.) is the most romantic choice you can make for a dinner à deux, with flattering lighting and a small, seasonal menu. The chocolate olive-oil cake is a perennial favorite, and perfect for splitting.
Quick nightcap, or keep it going?
Now you have a decision on your hands. The predictable choice would be to grab a cocktail at one of the several nearby bars — Wally's, Zymarium, Guesthouse etc. — and you wouldn't go wrong imbibing at any of those establishments. But if you feel a spark and don't want the day to end, a trip to the Enzian Theater (1300 Orlando Ave., Maitland), our only arthouse cinema, makes for a magical capper to a magical day. The building surrounded by oaks dripping Spanish moss is charming, and the cuddle-friendly seating indoors has led to many, many relationships launched on these quaint Maitland grounds.
Date No. 2:
Start the evening at Light on the Sugar Bakery
Take a break from Starbucks at this French/Asian fusion bakery and café. There are two locations, and the Winter Park one (4270 Aloma Ave.) is open until 8 p.m. It'll be a delightful dilemma to choose just one among the exquisite selection of treats: Will it be the fluffy matcha croissant, the velvety ube macaron, or perhaps the rich and nutty black sesame éclair? You and your partner can opt to enjoy your treats in the cozy ambience of the bakery or take them to go, as our next location welcomes drinks and snacks.
Get creative at All Fired Up
Ignite your creativity and spark a romance at this cute, funky pottery painting spot. With over 200 clay pieces to choose from, you and your partner can channel your inner artist. Whether you opt for solo masterpieces or combine your artistic forces, it's a fun chance to create something unique together and test out your teamwork skills.
Fuel up at the Park Avenue Tavern
If you're hungry from all your creative work, grab a bite to eat at the newly opened Park Avenue Tavern (558 W. New England Ave., Winter Park). The NYC-influenced decor brings a more serious vibe to the table, allowing the perfect space to get into those necessary deep conversations. Clubby though it is, the restaurant retains a lighthearted feel that doesn't fully weigh down the mood with its comfortable booth seating, natural lighting, and live music.
End the night at the Axe Trap
If things are going well and you don't want the night to end just yet, roll on over to the Axe Trap (2600 Lee Road). At Winter Park's first-ever axe-throwing venue, enjoy signature cocktails, a bite to eat or a well-brewed coffee in a circa-1920s industrial warehouse. It's the perfect blend of caffeine and adrenaline, ensuring a date that's sharp, stimulating and hits the bull's-eye.
Date No. 3:
Meet at Stardust Video & Coffee
Rendezvous at this Audubon Park staple (1842 E. Winter Park Road) to grab a drink and work through all the getting-to-know-you chitchat jitters. The bartenders serve up all the spirited staples, and most nights you'll also find a menu of specialty cocktails. There's a lot of disaffected cool in the air here, but what do you want, the robotic politeness of Chick-Fil-A? (Watch your date react!)
Grab a bite at Bikkuri
Yes, there's Tori Tori right down the road, but this second-floor sushi destination (1919 E. Colonial Drive, upstairs) is great for the dating dynamic. Slide into a booth and order some rolls or sashimi to split — or a boat if you're trying to really razzle-dazzle — and sip some tea, Kirin or a cocktail while negotiating the next stop at ...
Catch a gig
By this point you're both weary of small talk but would rather die than talk about politics/religion, so why not go catch some live music? Do you go to Uncle Lou's? Will's Pub? Timucua? Conduit? The Abbey? Do you stick to local bands or catch a touring act? Do you head for the front and park yourself in front of the stage or linger in the back? It's a cornucopia of Rorschach tests! Inspired by some audio artistry or ready to roast the no-hopers you just witnessed, keep this party rolling ...
End the night with a drink — but where?
You're now caught in the date-night version of Robert Frost's "Stopping by Woods on a Snowy Evening." You could pop into Lil Indie's or Sunroom and grab a very specialty beverage to sip with your companion while people-watching, or you could storm into Whiskey Lou's or St. Matthew's or Caboose. Do you still tolerate each other? Are you attempting to prolong the evening, or ditch this loser? These are decisions that you must make soon, as last call approacheth. Choose wisely. We've got faith in you, tiger.
