People seem to think that dating needs to be expensive. We at Orlando on the Cheap feel that this does not need to be so. Orlando offers many options to make sure your dates are not only romantic, but also friendly on your budget. Here is our roundup of romantic Orlando dates under $30.
ARTS, CULTURE & MUSIC
- Frontyard Festival
The Dr. Phillips Center has transformed its huge lawn into a dedicated outdoor entertainment venue showcasing a lineup of music, comedy, film and more. Experience the Central Florida’s local arts scene from the comfort of your own pod during the most beautiful time of year in Orlando. Tickets start at $5 per person for some of the events. Check out the Frontyard Festival schedule to schedule your next date night.
- 1st Thursdays at Orlando Museum of Art
The first Thursday of each month, the museum showcases a new theme of art by local artists accompanied by live music, a cash bar and café with selections by area restaurants. Tickets are $15 and include admission to the museum’s featured exhibitions.
- Bach Festival Society
Add a little culture to your date night calendar with community events by the Bach Festival Society. Check their website for special events throughout the year.
- Sanford Art Walk
Stroll through art venues, mingle with artists, and enjoy live music on the fourth Friday of every month. While in downtown Sanford, take in the views of Lake Monroe from the Riverwalk and stop at one of the best German restaurants, Hollerbach’s Willow Tree Cafe, where you can prost (cheers) with Das Boot, share a gigantic pretzel and enjoy live authentic German music.
- WineArt Marketplace in Lake Mary
On the first Wednesday of every month, this event features local artists, food trucks and a beer and wine garden. Stroll along the sidewalk lined with displays by local artists, sip on wine and listen to live music in Central Park.
- Casselberry Art & Music in the Park & Food Truck Bazaar
Spend an evening at the beautiful Lake Concord Park in Casselberry to enjoy live music, artisan booths and a variety of culinary flavors from local food trucks. Held the second Friday of every month from 6 p.m. to 9 p.m.
- Thornton 2nd Thursday Wine & ArtWalk
On the second Thursday of every month, celebrate the arts with an evening of food, wine, shopping and showcases by Orlando-based artists. For $10 (pre-sale ticket price), you’ll receive a wristband, wine glass and a map of 25+ locations where you will be greeted with a complimentary libation.
- Visit Mount Dora
With quaint streets, boutiques, and small-town charm, Mount Dora is one of the most romantic towns in Central Florida. There are plenty of special events throughout the year like the Lighting of Mount Dora during the holidays and art and craft festivals; but any day is a good time to check out this local gem.
- SAK Comedy Lab
The couple who laughs together stays together. Get your giggle on at SAK Comedy Lab where a professional ensemble of improv actors graces the stage every night. Tickets are reasonable and they usually offer a Florida Resident special.
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- Enzian Theater
This alternative cinema offers independent, foreign and classic films and has arguably one of the prettiest outdoor bars in Orlando, Enzian’s Eden Bar. It also hosts the monthly free outdoor movie series, Popcorn Flicks in the Park, in Central Park.
- Movie Night at Leu Gardens
On starlit evenings, you and your sweetie can snuggle up on a blanket in the beautiful 50-acre Harry P. Leu Gardens. Hundreds of lovebirds flock to Date Night at Leu Gardens on the first Friday of most months (and Valentine’s Day) when the outdoor screen shows romantic flicks and blockbuster hits. Tickets are just $6.
FOOD & WINE
- Wine Room at Winter Park
Wine aficionados and newbies alike will enjoy a DIY wine tasting experience at The Wine Room at Winter Park, where the Enomatic Wine Serving System gives guests the chance to sample selections of over 150 different types of wine simply with the touch of a button. Couples load up a debit card with cash and then wander through the living room-esque locale sipping wines and noshing on gourmet cheese plates.
- The Food Truck Bazaar
The Food Truck Bazaar offers couples an atypical dining experience with a reputation for gourmet food like lobster rolls, chorizo tacos and root beer flavored cupcakes. Don’t forget chairs or a blanket; seating is typically scarce.
- Lakeridge Winery
Travel through the rolling hills of Clermont for an unexpected Florida wine experience. Lakeridge Winery entertains visitors with free or inexpensive ($5-$10) events featuring live music, artist vendors, crafts and food. You can also stop by any day of the week for complimentary wine tours and tastings.
- Farmers’ Markets
Buy fresh flowers for your date, taste local fare and stock up on produce to cook dinner together. Our favorite markets are Winter Park on Saturdays and downtown Orlando with live music and a wine/beer garden on Sundays. We also love to shop at Plant Street Market in Winter Garden and East End Market in Orlando. Both are indoor markets that are open daily.
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- Pick your own strawberries
If you are interested in harvesting your own fresh fruit at a local farm, check out Oak Haven in Sorrento where you can pick strawberries and sample wine on the weekends. Throughout the year, you can also pick your own blueberries, visit sunflower fields, pick pumpkins during the fall season, and explore other U-pick farms near Orlando.
There’s nothing more romantic than a picnic, especially in a picturesque setting. Fortunately, Orlando has many to choose from such as: Lake Eola in downtown Orlando, Cranes Roost Park in Altamonte Springs, or Central Park and Azalea Park in Winter Park. Pack a spread of finger foods, a bottle of wine and blanket for a relaxing day at the park.
- Old Sugar Mill Grill at De Leon Springs
Start off your morning by making your own pancakes at the Old Sugar Mill Grill located next to the natural swimming hole of De Leon Springs. The server will provide you with the batter and toppings for you to cook on your own griddle. After your meal, take a dip in the chilly springs or rent a canoe.
- Sample local brews
For beer connoisseurs, brewmasters mix up fermenting magic at a variety of local breweries. Stop by one of these breweries for a flight or pint: Orlando Brewing or Ivanhoe Park Brewing Co. in downtown Orlando, Sanford Brewing in Sanford and Maitland, Crooked Can Brewing Company, and the flagship of Plant Street Market in Winter Garden. For more breweries in Orlando, check out this list.
RECREATION & ATTRACTIONS
- Orlando Sports
Orlando has a wide variety of teams to support including Orlando Magic basketball and Orlando City soccer. And for the most part, you can find tickets for a reasonable cost. Orlando Solar Bears hockey tickets start as low as $20 each.
- Lake Eola Swan Boats
Paddle out on Lake Eola via a swan boat during the next warm evening. Boat rentals, which cost $15 per half hour, can be secured at the swan dock across from Relax Grill. Reservations are not required.
- RDV ice-skating
Don’t forget your sweaters and socks when you visit to RDV’s Ice Den, where the Olympic size ice skating rink is kept at a chilly 50 degrees Fahrenheit. Skate rentals, as well as hot chocolate, are available on site. If a solid, dry floor is more your speed, Semoran Skateway Rollerskating, has an adult night every Sunday.
- Winter Park Boat Tour
Float through the canals and lush landscape of Winter Park’s waterways on a tranquil Scenic Boat Tour. The hour-long tour is $16 for adults.
- The Springs
Think about renting a canoe at Wekiwa Springs, a tranquil and untouched state park north of Orlando where a beautiful spring and river gives couples the option for swimming and kayaking. During a cold snap, put the Blue Springs on your list for a chance to spot hundreds of manatees. Check out more of Central Florida’s natural springs.
- Wekiva Island is that secret watering hole locals don’t want visitors to discover. Located along the shore of spring-fed Wekiva River, this eco-friendly oasis has it all — from recreational activities to a bar that serves beer and wine. Spend the day lounging in Adirondack chairs, playing volleyball, swimming in the cool waters and listening to live music. Admission is free during the week, and the charge is usually only a dollar or two on the weekends.
- Go for a hike
For a true Florida primitive adventure, hike through Black Bear Wilderness Trail, a 7.1 mile loop through wetland habitats and along the St. John’s River.
- Stroll through gardens
- Harry P. Leu Gardens: 50-acre botanical oasis boasting a rose garden, butterfly garden and a vegetable garden. $10 for adults, $5 for kids and free for 3 and under. Free entry on select first Mondays.
- Mead Gardens: free 47-acre park with an amphitheater, butterfly garden, boardwalk and bike trail.
- Kraft Azalea Gardens: free with old cypress trees, a fountain, benches and a view of Lake Maitland.
- Rent bikes or scooters
Explore the City Beautiful with your date by renting bikes or scooters through the Orlando Bike Share program. Simply reserve a bike/scooter online or through the app, release the ride and then return at any one of the designated stations.
- Ride the Sun Rail
Another fun way to explore together is by riding the SunRail. Stop off in Winter Park for lunch on Park Avenue or take the train to Church Street for a cocktail and apps.
- Lake Apopka Wildlife Drive is an 11-mile drive with a chance to view native animals in their natural habitat including 174 bird species. The drive is open Fridays, Saturdays and Sundays.
- Explore the trails
Seminole County’s award-winning recreational trail system is a Central Florida best kept secret with more than 60 miles of paved and natural trails. Whatever adventure you choose, it’s free to journey through the trails of Central Florida. Explore Central Florida’s trails:
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- The Wheel
Take a ride on the observation Wheel for breathtaking views of Orlando from 400-feet up. After the ride, explore the shops, experiences and restaurants at ICON Park.
THEME PARK EXPERIENCES WITHOUT A TICKET
With a nod to Central Florida’s refreshing natural springs, this outdoor escape features 120-acres of unique boutiques, award-winning restaurants and lively entertainment in four distinct neighborhoods: The Landing, Marketplace, West Side and Town Center. Relax by the water, stroll through shops, make fun memories and take plenty of selfies.
Check out the latest Florida Resident deals for Disney.
This action-packed hotspot features an eclectic collection of themed restaurants, nightclubs, a movie theatre, shopping and non-stop entertainment. Parking at City Walk is free for everyone after 6 p.m. Take in the sights and sounds, and then board the free water taxi service to cruise canals that meander throughout Universal Orlando Resort. Hop off to explore the resorts and entertainment along the way including Musica della Notte (Music of the Night), a free evening of music at Loews Portofino Bay Hotel.
Take a step back in time at Disney’s Boardwalk, a quarter-mile promenade boasting endless charm and architecture inspired by 20th century coastal destinations like Coney Island. Watch street entertainers, take a boat ride through the Disney waterways, and tour one-of-a-kind shops.
Romantic things to do in Orlando that are ON HOLD at this time:
- Moonlight Walking Tour at Greenwood Cemetery
If your date appreciates history and isn’t afraid of the dark, stroll through the Moonlight Walking Tour at the historic Greenwood Cemetery. Explore the 100-acre cemetery with visits to 100 graves of notable individuals in Orlando’s history like T.G. Lee, James Parramore and Joseph Bumby. The tour is free, but advance registration is required and donations are accepted.
- Music at the Casa
Casa Feliz in Winter Park opens its doors on Sunday afternoons from 12 p.m. to 3 p.m. for live music and free tours of the historic house and James Gamble Rogers II Studio. Bring along a picnic to enjoy in the beautiful flower gardens. Entry is free but donations are accepted ($5 suggested).
Take your date night out of this world, literally, with a visit to the Planetarium at Seminole State College where weekly interactive shows bring thousands of stars and the stories behind them into clear view. Cost per person is typically $6 (cash only).
MORE THINGS TO DO IN ORLANDO:
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- Outdoor movies in Orlando
- Orlando Happy Hour Specials
- Best free and cheap outdoor adventures in Orlando
- Outdoor movies in Orlando
- Best Groupon deals for things to do in Orlando
- Bottomless mimosas and brunch in Orlando
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By Laura Perry & Kristen Manieri, founder of Orlando Date Night Guide, a website that’s been giving date night ideas to Orlando couples since 2007.