25 Romantic Orlando Dates under $25

By Laura

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 has a few things to make sure your dates are not only romantic, but also friendly on your budget. Here is our roundup of 25 romantic Orlando dates under $25.

ARTS, CULTURE & MUSIC

1^st 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 $10 and include admission to the museum’s featured exhibitions.
Bach Festival Society

Add a little culture to your date night calendar with free community events by the Bach Festival Society. Check their website for special events throughout the year.
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.
Art & Music in the Park

Snuggle up for a fun evening under the stars with live music and culinary delights from the Food Truck Bazaar at Concord Park in Casselberry. Free entry.
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.
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 with Das Boot, share a gigantic pretzel and enjoy live authentic German music.
Stargazing

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.
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 Mount Dora Art Stroll, 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 giggles at SAK Comedy Lab where a professional ensemble of improv actors graces the stage every night. Tickets can start as low as $5 each for select shows.

FILM

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.
Date 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 when the outdoor screen shows romantic flicks and blockbuster hits. Tickets are just $6. There are many free outdoor movies in Orlando as well.

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

With over a dozen starlit shindigs scheduled each month, 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. One weekend every month, the Lakeridge Winery entertains visitors with free (or $2 donation entry) 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. 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.
Picnic

There’s nothing more romantic than a picnic, especially in a picturesque setting. Fortunately, Orlando has many to choose from such as Lake Eola, Cranes Roost, Central Park or 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.
Thornton Park Wine & Art Walk

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, you’ll receive a wristband, wine glass and a map of locations where you will be greeted with a complimentary pour of wine. The Lake Mary WineArt Wednesday features local artists, the Daily City Food Truck Bazaar and a beer and wine garden on the first Wednesday evening of every month.

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 at $15. Check out the Baseball Spring Training schedule that includes the Atlanta Braves at Disney.
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. On Friday and Saturday evenings, DJs fill the rink with TOP 40 tunes for the coupled-up skaters gliding across the ice. Skate rentals, as well as hot chocolate, are available on site.
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 $12 for adults.
The Great Outdoors

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. Rent tubes and float through the cool spring at Kelly Park/Rock Springs Run or check out another one of Central Florida’s natural springs. Rent paddle boards at Wekiva Island. Or perhaps rent some bikes and head for a ride along the West Orange Trail or Seminole Wekiva Trail. For a more primitive adventure, hike through Black Bear Wilderness Trail, a 7.1 mile loop through wetland habitats and along the St. John’s River.
Rent bikes

For $5 an hour, you can explore the City Beautiful with your date by renting bikes through the Orlando Bike Share program. Simply reserve a bike online or through the app, release the bike to ride and then return at any one of the designated stations. 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.
Disney’s Boardwalk or Disney Springs

Take a step back in time with an evening stroll along Disney’s Boardwalk, a quarter-mile promenade boasting endless charm and architecture inspired by 20th century coastal cities like Coney Island and New Jersey. Watch street entertainers, enjoy an ice cream cone or Saltwater taffy from Seashore Sweets’ and tour unique shops, restaurants and nightlife venues. Disney Springs features an eclectic and contemporary mix of 150 establishments including shops, restaurants and other venues.

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.