Date Night Ideas in Winter Garden

Central Florida has a lot to offer in the way of fun date night ideas. Although it’s easy to assume, it’s not all about major attractions like theme parks.

Winter Garden is an area with a growing population, and it offers a lot of appealing activities for couples. If you live in Central Florida, here are a few charming date night ideas in Winter Garden to help keep that spark in your relationship.

Browse All Plant Street Market Has to Offer

Open until 7 PM Monday through Friday and 6 PM on the weekends, this eclectic market has something for everyone. 

Browse artisan vendor stalls offering handcrafted items, essential oils and more. If you’re feeling tired, take a quick stop at the Oxygen Bar and get a recharge.

When you’re feeling hungry, choose among the numerous tasty eateries or grab a beer at the Crooked Can Brewery. For those who’d rather cook at home, stop at the butcher for some fresh cuts of meat and organic vegetables.

Plant Street Market is vegan friendly and a great place for you to bring your pets too!

Enjoy an Elegant Dinner Out

Treat yourselves to a night out of fine dining at the Chef’s Table at The Edgewater. You’ll quickly find out why they’ve been voted Most Romantic Restaurant more than once!

If you prefer something a little more laid back, check out the Tasting Room. Not only do they share a kitchen with the Chef’s Table, their small plates are tasty and often accompanied with live music.

Grab Some After-Dinner Drinks

Pilars is a bar that’s all about martinis, music, mixology and more. If you’re looking to grab a quick drink or sip the night away, this is the spot.

Located in the heart of historic Winter Garden, this little joint sets the mood with dark lighting and talented bartenders. Let this Winter Garden gem help set the mood for your date night evening.

Kick Off Date Night With Fridays on the Plaza

It’s Friday night and you’re ready to bring on the weekend fun with your sweetheart! What better way to do that than some stellar beats?

Downtown Winter Garden can help you kick off weekends right with live music. As its name suggests, Fridays on the Plaza happens every Friday from 7 to 9 PM. Here’s a peek at their nightly themes for the month of May:

  • 5/3 – Crenshaw (Folk)
  • 5/10 – Porchdogs (Cajun – Zydeco)
  • 5/17 – Scotty Long (Country – 60’s – Today)
  • 5/24 – Good times Jazz Band (Jazz)
  • 5/31 – Tree Frogs (Classic Hits – 60’s & 70’s)

Attend a Show At the Garden Theater

Take your sweetheart out for a night to remember! The Garden Theater offers live plays, concerts, films and more. With exciting live shows including Flashdance, A Christmas Carol, and Roald Dahl’s Matilda, you won’t want to miss out.

Head over to their webpage to check out upcoming shows and get your tickets before they’re sold out!

Top Date Night Off with a Cold, Refreshing Ice Cream

Whether you’re coming from a concert, dinner or a show, dessert is a great way to end the night. Hop on over to Frozen Cow Ice Cream for a tasty sweet treat.

Their exciting flavors range from Cookies N’ Cream to Blueberry Cobbler. For those who are lactose intolerant or sugar sensitive, good news! They offer dairy-free and sugar free options too. 


Hopefully you enjoy these date night ideas in Winter Garden. Did we miss anything? Let us know your favorite date night places to go in the comments!