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. 

1. 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.
2. 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.
3. 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.
4. Wednesday Night Pitcher Show
   Arguably one of the prettiest bars in Orlando, Enzian’s Eden Bar hosts the weekly Wednesday Night Pitcher Show, a laid-back cocktail party featuring a retro classic film on a giant outdoor screen. Jell-O shot movie trivia add to the fun.
5. Lakeridge Winery
   Travel through the rolling hills of Clermont for an unexpected Florida wine experience. One weekend every month, theLakeridge 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.
6.  1^st Thursdays at Orlando Museum of Art
   The first Thursday of each month, the Orlando Museum of Art 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.
7. 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 in Winter Park including one of our favorites, Spring Pops in the Park.
8. Farmers’ Markets
   Pick out fresh flowers, taste local fare and stock up on produce to cook dinner together that evening. Our favorite markets are Winter Park on Saturdays from 7 a.m. to 1 p.m. and downtown Orlando on Sundays from 10 a.m. to 4 p.m.
9. 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.
10. 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 until 7pm Sunday – Tuesdays, and until 10pm Wednesdays – Saturdays. Reservations are not required.
11. 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.
12. 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.
13. 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.
14. 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 take a walk around the park.
15. 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.
16. 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.
17. 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.
18. Friday Night Live
    The Eddie Rose Amphitheatre at Uptown Altamonte hosts local bands for Friday Night Live, a weekly live music most Friday nights beginning at 7 or 8pm. Free and open to all music lovers, the outdoor concert features an ever-changing line-up of musical styles, from calypso to rock to jazz. Afterward, take a stroll through Cranes Roost Park, where a 1-mile lakeside trail winds through the 45-acre park.
19. Trivia Nights
    Engage the heart and the mind with a little mental stimulation on your next date night: Earth Trivia is played at bars and restaurants all over the Orlando area seven nights a week. The game is divided into rounds of ten random questions that you answer as a team. You write your answers on the sheets provided and then hand them in at the end of each round. Winners are announced and prizes (usually gift certificates to the restaurant) are given away.
20. 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 natural spring at Kelly Park/Rock Springs Run. Or perhaps rent some bikes and head for a ride along the West Orange Trail or Seminole Wekiva Trail.
21. Lake Mary WineArt Wednesday
    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. Walk along the sidewalk lined with displays by local artists, sip on wine and listen to live music in Central Park next to Lake Mary City Hall. Entry is free but bring cash for unique finds, food and drinks. The event is just a short walk from the Lake Mary SunRail station.
22. 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 at the Thornton Park Wine & Art Walk. 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.
23. Sanford Art Walk
    Stroll through art venues, mingle with Central Florida artists, and enjoy live music at the Sanford Art Walk 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 in the United States, Hollerbach’s Willow Tree Cafe. Prost with Das Boot, share a gigantic pretzel and enjoy live authentic German music.
24. Rent bikes in downtown Orlando
    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.
25. Disney’s Boardwalk
    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.