Things to do for Valentine's Day in Orlando

The Orlando Main Streets Program was developed in 2008 as a way to strengthen Orlando neighborhoods as part of the Main Street America movement. Today, there are 10 Orlando Main Street Districts, each with their own signature flair and walkable hub of restaurants, shops, bars and landmarks.

As an added bonus, each district just happens to boast endless activities for date night. Do yourself a favor and visit one–or all–of these districts to support local business and makers while discovering another source of pride for the city where you live and do date night.


Ivanhoe Village is so romantic it was named one of the three Most Romantic Main Streets in 2017! Besides romantic eateries and cozy bars, the district is a haven—literally—for art lovers. Loch Haven Cultural Park is home to multiple theaters and museums including Orlando Shakes and the Orlando Museum of Art. The latter hosts regular hands-on workshops for adults as well as a monthly 1st Thursdays after-hours event. Annually, the park hosts the Orlando Fringe Festival, a multi-day uncensored and unjuried arts festival showcasing performance art and more.


If you’d prefer to create art instead, Factur is a creative co-working space, which hosts weekly open houses and hands-on workshops, like glassblowing and woodturning.

Dine on shareable tapas at Santiago’s Bodega (try happy hour for $3 sangria and $5 tapas) or watch the sun dip below the horizon from the lakefront patio at Mesa 21 or the rooftop of M Lounge. No matter what you do, don’t leave the district without dessert at Better Than Sex. This sultry dessert-only restaurant is decked out with risqué art on the walls and a decadent menu of naughtily named desserts and chocolate-rimmed glasses of dessert wine.

Santiago's Bodega Orlando happy hour
Santiago's Bodega | Image credit: Stephanie Patterson

Dine & Drink



For a quintessential Orlando date, the Thornton Park District can’t be beat. Here you’ll find the iconic Lake Eola Park, a fixture for weekly community events and too many Orlando proposals to count. You can take to the water in a romantic swan paddleboat for a closer look at the fountain, or walk the paved trail around the lake checking out art installations along the way. The park is also home to the weekly Orlando Farmer’s Market and a community yoga class on Sundays.

Lake Eola Swan Boat ride
Lake Eola Swan Boats. Image credit: Arlene Laboy

Once you’ve worked up an appetite, there are dozens of restaurants and bars dotting the brick-lined streets. Dine on Southern fare at Soco. The restaurant has a patio, delicious weekend brunch menu, and date night ambiance. For dessert, savor artisan ice pops at The Pop Parlour (they’ve even got booze-infused pops) or inventive ice cream at The Greenery Creamery.


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yoga in orlando
Yoga at Lake Eola Park, Sundays at 11am


On a budget? Orlando’s Mills 50 district is one of the best places to do date night for under $50. It’s also one of the most culturally diverse districts, home to impressive street art, multiple LGBTQ organizations, and restaurants covering a multitude of cuisines. You can’t visit Mills 50 without spending some time appreciating the colorful murals, electrical boxes and dumpsters. Rent a Juice bike by lil’ indies and set off to see how many murals you can find, or follow this self-guided street art tour to visit a few of our favorites.

Black Rooster Taqueria is one of our favorite local taco establishments, and it’s classy enough for a casual date. Prepare yourself to taste the best made-to-order guac in town along with authentic tacos like the Black Rooster Asada and Crispy Fish. Afterwards, head next door to The Guesthouse for craft cocktails served in a classy setting. In Orlando's Little Vietnam, you can nosh on everything from pho at Pho 88 Vietnamese Restaurant and Laos street food at Sticky Rice to bao at King Bao and authentic Vietnamese eats at Little Saignon. For farm-to-table eats try The Strand, which sources ingredients from local farms and also serves a killer Saturday brunch.

Date Night in Orlando's Little Vietnam
Image credit: Kelsey Glennon

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Mills 50 district mural
Mural by Andrew Spear on Shine & Colonial. Image credit: Arlene Laboy


From a lush 50-acre botanical garden to an indoor food market and enough dessert-centric eateries to earn the nickname of the “dessert district”, Audubon Park has something for everyone. This eco-friendly neighborhood also hosts an assortment of fun events including a weekly community market.

Harry P. Leu Gardens is a fixture of the district, boasting 50 acres of manicured gardens and a monthly movie night (first Friday of most months). Pack a picnic and your favorite bottle of wine to enjoy while you watch a flick outdoors. For a more active date, join a walking food tour with Mosquito County Tours, or hop on your bike to partake in a Fleet Farming Swarm Ride to tend to community gardens.

The central hub for foodies is East End Market, home to a multitude of food purveyors, a coffee shop, Domu (the best ramen in town) and several local vendors. Date night must-dos include the weekly grilled cheese happy hour at La Femme Du Fromage, sinking your teeth into a gigantic Gideon’s Bakehouse cookie, and listening to free live music on the patio each Saturday. Cross the street to savor a scoop of homemade ice cream at Kelly's (try the Mexican chocolate!). Get your drink on at Redlight Redlight, a craft brewery and beer parlour with more than 30 beers on tap and even more selections available by the bottle.

East End Market
Image credit: East End Market

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Orlando Events for September 2018
Leu Gardens movie night | Image credit: Leu Gardens


The iconic Church Street District is our go-to for a fancy night out in downtown Orlando. Church Street Station, Orlando’s original train station, serves as a centerpiece with dozens of restaurants and bars lining the streets.

The Church Street District dates back to the 1800s so start your date by taking a self-guided walking tour of the area’s historic buildings. This map will give you details and background along the way. Get your game on at Hamburger Mary’s for a round of trivia every Wednesday, or watch a sporting event at Amway Center, home to the Orlando Solar Bears and the Orlando Magic. Soccer fans can celebrate at Lion’s Pride, a dedicated soccer fan bar and restaurant, before heading to Orlando City Stadium for a match.

Classy options for a dinner date are plentiful, from the swanky Kres Chophouse to Ceviche Tapas. If you’re in the mood for a classic dinner and a movie date, dine at Chela Tequila & Tacos before heading to Cobb Plaza Cinema Café for a flick.

Church Street District Date Night Itineraries
Image credit: Church Street District

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More Orlando Main Street District date nights:

Florida food and travel photographer and writer Stephanie Patterson

About the Author/Photographer:
Stephanie Patterson is the editor of Orlando Date Night Guide. She’s a talented professional food and travel photographer and writer with a passion for creativity, the beach and great eats. When she’s not taking photos or writing, you can find her exploring the state for her Florida travel blog, Travel Taste Click. Find her online at and