29 Unconventional Date Ideas in Orlando

Since I’ve lived in Orlando all of my life, it never surprises me when someone on campus asks me what I like to do for fun. I usually start with the tourist-inspired destinations. I’ll rattle off the most obvious (I’m paying for both Disney and Universal annual passes so this is my only opportunity to brag about it), and then talk about their counterparts; Disney Springs and CityWalk. However, since I did mention that this question is most frequently asked on college grounds, the follow-up question is usually along the lines of a rephrased one.

"I mean, like… What do you like to do for fun… that’s cheap?”

This is the part where I admit my parents are paying for both those annual passes.

As I’ve continued through my college experience, many of my friends have met boyfriends/girlfriends, and the tourist destinations often make for expensive and repetitive afternoons. When the topic of date ideas with the college budget in mind comes up, many of my peers are reduced to ramen a la dorm experiences by the romantic candlelight of their portable mini fridges. After a close friend of mine begrudgingly told me how her boyfriend decided to make her dinner in his apartment by throwing a slice of cheese on dinosaur chicken nuggets and called it chicken parmesan, I refused to let the sacred art of college dating die. Instead of saving up money to splurge once a month on date night, I scoured my hometown (and a few surrounding areas) for the cutest, thriftiest, underground, or unique date venues that won’t require you to take out more student loans.


Stardust Video & Coffee – In the afternoon, Stardust Video & Coffee is a relaxing space for deep conversation or to unwind with a group. At night, the venue stages free concerts, skits, and movies. There are board games to play, books on the shelves to read, and special events from local artists. This makes for a fantastic group date playing games and supporting Orlando bands. 


Drunken Monkey Coffee Bar – This coffeehouse offers some of the best vegan food around. Every Friday and Saturday night Drunken Monkey Coffee Bar hosts free stand-up comedy. If sharing a dairy-free scone and listening to some of the funniest local comics sounds entertaining, it would make a unique, lighthearted date.


Sleeping Moon Cafe – In my personal opinion, their iced raspberry mocha is the most delicious coffee I’ve enjoyed throughout my coffeehouse-scouting. Much like Stardust Video & Coffee, Sleeping Moon offers free concerts and an aesthetic atmosphere. The menu is refreshingly healthy, and the portions of food are definitely worth the money. 

UPDATE: Unfortunately, Sleeping Moon Cafe is relocating. You can visit their relocation fund here to donate!


Austin’s Coffee – The atmosphere in Austin’s Coffee is a mixture of Bohemian and art deco. The live music is exceptional and the menu offers assortment ranging from freshly brewed coffee to wine and beer. It is a cozy nook perfect for curling up on their couches and having an intimate conversation. 


Vespr Craft Coffee & Allures – It’s a contemporary coffeehouse serving both coffee and organic, fair-trade teas. Most locals rave about its relaxing atmosphere that allows for more intimate conversation, and trendy coffee art. 


Downtown CREDO – The store is a nonprofit, donations-only business that contributes to charities such as Downtown and Parramore Branches of Central Florida Boys and Girls Clubs, New Image Youth Center, Keeping Orlando Beautiful, and Green Up Orlando. Downtown CREDO hosts live music and charity events. If your girlfriend/boyfriend is passionate about helping the community as well as coffee, it is a perfect casual afternoon to have. 


Natura Coffee & Tea – There are plenty of things to do at Natura Coffee & Tea that would appeal to almost everyone. The menu serves coffee and boba tea. Entertainment is almost nightly, and it includes everything from open mic nights to live music. It also has a large selection of hookah, if that is something you and your date enjoy. 


Boston Coffee House – This coffeehouse by far has the richest coffee in the area. The coffee art designs are colorful and the atmosphere resembles a cozy living room. Prices are a little more steep than the average Starbucks, but definitely worth it for the warm atmosphere and unique flavors of coffee. 


Krungthep Tea Time – Thai flavors are the biggest influence throughout their tea, sandwiches, and desserts. Krungthep Tea Time could definitely take your palate out of your comfort zone if you are looking for a special kind of date. 


Dandelion Communitea – It’s a colorful vegetarian restaurant with fresh food and live entertainment. The atmosphere is earthy and alternative. And if your girlfriend/boyfriend is interested in catching them all, its sign is also a Pokestop. 


Rabbitfoot Records & Coffee Lounge – In a room straight out of 500 Days of Summer, there is an immediate alternative vibe to Rabbitfoot Records & Coffee Lounge. It is a perfect date for a couple that enjoys sipping coffee and browsing through vinyl. One Orlando native once described it as, “a hipster location without trying too hard.” 


Black Bean Deli – There are three locations: mills50, Winter Park, and the Amway Center. All three include authentic Cuban cuisine for all times of the day. Enjoy a coffee date in the morning, or go in the afternoon for masitas de puerco served with rice, beans, plantains and a salad. There are also weekly specials to guarantee your favorite meal will be served. 


Ethos Vegan Kitchen – Many people are going vegan for reasons ranging from animal rights to eating healthier. If your sweetheart is on a strict diet, take them to this 100% vegan menu restaurant. Most of the food is organic, and it is served fresh daily. 


Gringos Locos – In my twenty years of living in Orlando, I have never found a better taco than at Gringos Locos. Not to be confused with the restaurant downtown, this particular location is in a small yellow building in the Milk District. From giant burritos to a late-night craving for cheese quesadillas, it’s the best date to have late at night under the fairy lights behind the restaurant. 


The Geek Easy – Are you and your date comic book readers? Ever wanted to combine your love of alcohol, live music, and fandoms? The Geek Easy is a comic-themed lounge with superhero-inspired drinks and events every week. 


BART // Bar + Arcade + Gallery – BART combines the best of 70’s, 80’s, and 90’s video games with craft beers and local art. It is half art gallery, half retro arcade.



Lake Eola – It’s hard to not have a romantic time out by the lake. Whether you take the swan boat ride, browse the local art and groceries at their Sunday market, bring your own picnic, or listen to live music in the park, the possibilities for a perfect date are endless. 


Winter Park Festivals – Winter Park hosts an abundance of events on its street to appeal to every type of date. Usually located on Park Ave, these festivals include art, food trucks, live music, and amazing sales. Some of the most anticipated festivals include the Bach Festival Society of Winter Park, Florida Film Festival, Winter Park Autumn Festival, and Winter Park Sidewalk Art Festival. My personal favorite as an Orlando native are their art festivals. I’ve never left without a new painting for my apartment and a few whacky accessories. 


Tasty Tuesday’s – Every Tuesday from 6:30 PM to 10 PM, local food trucks drive out to the Milk District to share their best cuisine. The venue is pet-friendly, and promise to show up rain or shine. 


Popcorn Flicks in the Park – Every second Thursday in Winter Park’s Central Park, the Enzian Theater screens a completely free movie. These films range from cult classics to family-friendly animations. It’s the perfect atmosphere consisting of old Hollywood under a starlit park. 


Date Night at Leu Gardens – Hosted in the beautiful venue of bright flowers and rolling (Floridian) hills, Leu Gardens shows movies for $6. Not only is the scenery breathtaking, but the movies appeal to a vast audience. It’s BYOB (bring your own blanket), and having a picnic is highly encouraged. 


Ocala Drive-In – Step back in time to one of the only lasting drive-in movie theaters in existence. The Ocala Drive-In features recent movies, but allows you to watch them from the comfort of your car. If your girlfriend/boyfriend is an old soul, it’s a romantic idea if you don’t mind the drive. 


Car Shows at Old Town – Old Town has recently been renovated to a shopping district with live entertainment, historical architecture, and distinctive storefronts that give Floridians a break from the typical theme park shopping plazas. One of Old Town’s most exciting events is their car shows. Whether you’re an automobile enthusiast or just a sucker for nostalgia, these cars always impress. They take a cruise down the street, and every model is dated before 1979. 


Canoeing at Wekiwa Springs – Wekiwa Springs is one of Florida’s most beautiful state parks. If your significant other has a thirst for adventure and a love of outdoors, this natural spring offers inexpensive canoeing and kayaking. Additionally, it is a breathaking destination to swim, lay out, and enjoy nature. 



East End Market – Filled with an array of artisanal vendors, East End Market is a shopping plaza dedicated to delicious food. The vendors offer cuisine from several different countries, and the atmosphere is modernly chic. 


Artegon Marketplace – One of the most diverse shopping plazas I’ve encountered, Artegon Marketplace has every kind of shop imaginable. There are kiosks filled with local art, records, games, clothing, and home décor. It’s the best destination to grab a coffee and come home with a souvenir. 


Adjectives Market – An upscale antique store, Adjectives Market has clothes, furniture, books, toys, and decorations from as early as the 1800's. Each room is well-stocked with thirft items you could only find at a quaint, eccentric gem like Winter Park.



Orlando Science Center – It’s a mixture between Wonder Works and NASA itself. The Orlando Science Center isn’t just a destination for elementary school field trips. The museum hosts adult events like Science Night Live for those over 21, and fun activities throughout the week. 


Record Stores – Whether you’re a rock ‘n roll junkie or just romanticize nostalgic music, there are plenty of record stores around Orlando to browse on a date. As an Orlando native, some of my absolute favorites with the best prices and atmosphere are:

  • Park Ave
  • Rock & Roll Heaven
  • Retro Records
  • R n R Record Shop


Orlando Museum of Art – Nothing is more romantic than interpreting art with someone you care about. The Orlando Museum of Art has various exhibitions from a vast array of esteemed artists. 


Special thank-you to Vicki S., Alaina O., Isabelle P., and Lisa C. for helping me develop this article.

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