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Date Night Guide: Winter Park Village

If you’re looking for date night inspiration or you just need a reason to get out of the house for a bit, here are some ideas and tips to make some new memories at Winter Park Village.

The Classic with a Twist

Whether this is your first date or your 10-year anniversary, a classic movie date never fails to leave you swooning. Regal Cinemas 20 is the premier movie theater in Winter Park, with comfy reclining seats and adult bevies available for your enjoyment. After the show, head over to Pizzeria Valdiano for a slice of pizza pie perfection.

PLAY Tip: Pizzeria Valdiano can create a pizza just for you and your date right in front of your eyes. Build your own and share the LOVE with your LOVE.

Foodie Fun

Curious culinary artists can test their knife skills at Publix Aprons Cooking School’s Couple Cooking classes. Each class offers demonstrations in making four recipes based on the evening’s theme — you and your partner will enjoy cooking together without having to do the dishes afterwards. The evening can continue with a nightcap at Ruth’s Chris Steak House and maybe even a dessert to-go.

PLAY Tip: May we suggest the Ruth’s Coffee cocktail and white chocolate bread pudding as a decadent end to a delicious date.

Self-Care Date Night

We can all agree that we don’t plan enough self-care in our lives. What about having a special date night that focuses on recharging your batteries both psychically and mentally? The Bar Method is sure to have you both working up a sweat. Then soothe sore muscles and get that glow-up at Hand & Stone Massage and Facial Spa.

PLAY Tip: Call the spa ahead of time to book your appointment and check for offers to enhance your experience.

Adventures in Brunching

Who doesn’t LOVE a brunch date? Try something from Another Broken Egg Cafe’s incredible selection of both seasonal and traditional menus that will leave you feeling fueled for adventure. Then stop into REI Co-op to check out things you need for camping, biking, hiking, water sports and everything in between.

PLAY Tip: REI offers classes for outdoor enthusiasts who want to learn even more about camping, nature photography, trail hiking and more.   

A Rocking Evening Out

Don one of your favorite, well-worn band t-shirts and get your groove on at Guitar Center, the nation’s leader in music equipment sales. This store is filled to the brim with everything from ukuleles to turntables. Then stop by Starbucks for a coffee and laugh while chatting about your favorite one-hit wonders.  

PLAY Tip: Be your own rockstar! Select what instrument you want to learn and sign up for in-store or online music lessons at the Guitar Center.

Treat Yo’ Self

This date will have you singin’ “Treat Yo Self 2020” à la Donna and Tom from Parks and Recreation. Indulge in a bit of a shopping spree by splurging on some sexy scents at ULTA, and then head over to The Cheesecake Factory for a dinner that will leave you feeling first-class fabulous. Feeling a bit luxurious after all of that? Check out the seductive stylings of Soma, a lingerie lover’s dream, and then top your look off with dazzling details from Versona.  

PLAY Tip: Versona is an excellent place to pick out a date night outfit that won’t break the bank.

Sushi, Selfies and Shopping

A simple evening is sometimes best spent enjoying the things you love, like sushi, sake and a little shopping. Sakari Sushi’s menu has something for everyone. After a sunset soosh session, we highly suggest you head over to the fountain for a sweet selfie. Top off your evening at children’s boutique Masion Baby & Kids and pick up something cute for the kiddos.

PLAY Tip: Masion Baby & Kids is a trendy boutique featuring clothing, gear and gifts for babies, toddlers and kids. Stay up to date on their newest arrivals by following them on social media. Plus, they offer free gift wrapping in store.

Feeling Lucky Date Night

Celebrate the Lunar New Year and all the luck that it will bring with the Lucky Number 8 Menu from P.F. Chang’s and then challenge your date to a game of giant chess or checkers to test your good fortune. You and your lucky date can end the evening checking out the gifts, vintage wares and more in Adjectives Market.  

PLAY Tip: Tradition is very important when honoring the Lunar New Year. For example, households should refrain from sweeping, which may eliminate good luck!

Ladies’ Night Out

Girl, gather your lady gang and get out for a night of gal talk. Stop by Clean Juice for an organic fresh-pressed juice or smoothie, then head to Pristine Nail Lounge for a mani/pedi. With your nails looking just right, you’ve probably laughed yourself into a serious appetite. Bar Louie is a great space for specialty cocktails and dinner to celebrate the soul sisters in your life.  

PLAY Tip: Plan your evening out to enjoy a little LIVE entertainment at Bar Louie, starting each Thursday night at 6 p.m.

Dudes’ Night Out

Dads don’t have to skip a night out with their buds. Get your friends together and celebrate that bromance with a hand-crafted burger and carefully curated beer from The Hangry Bison. After dinner, you’ll want to stop into Warhammer, an amazing store filled with sci-fi and fantasy miniatures all made for gaming!

PLAY Tip: Check out the Belgian Flight at The Hangry Bison, featuring local Belgian-style beers from around Central Florida.

Mother’s Day Promotion

Spend $150 at Winter Park Village shops and restaurants to receive 2 free movie tickets!

  • Purchases totaling at least $150 must be made at Winter Park Village between Monday, May 2 and Friday, May 6, 2022.
  • Present receipts on the above dates at Versona or Maison Baby & Kids anytime between 11 a.m. and 6 p.m.
  • Limited supply of Regal tickets allocated to this promotion. One pair of tickets per person. Bill payments excluded. Promotion excludes Winter Park Village employees.
Written by
Wendy Meyer

Wendy Meyer is a Winter Park mom to son, Beckett, a self-proclaimed #Disnerd and an integral collaborator at PLAYGROUND Magazine. She currently holds the titles of social media manager, events editor and writer. (That's what happens when you're good at everything they throw at ya!) You can read her single-mom musings on her blog: Mommy’s Little Rebel.

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Written by Wendy Meyer


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