Dinner and a Movie

One classic date night idea that never gets old is dinner and a movie. Start your evening by enjoying a delicious meal at Ravenous Pig, known for its upscale American cuisine and craft cocktails. After dinner, catch a movie at Regal Winter Park Village, where you can snuggle up and enjoy the latest blockbuster.

Alternative options
– The Glass Knife (restaurant) and Enzian Theater (indie movie theater)
– Luma on Park (restaurant) and Amstar 12 (movie theater)

On-Demand Childcare in Your Neighborhood

Book a Sitter

Ice Skating at RDV Sportsplex

Embrace the winter season by hitting the ice with your partner at RDV Sportsplex Ice Den. Whether you’re a seasoned skater or a beginner, ice skating is a fun and romantic way to spend time together. Hold hands as you glide across the ice and enjoy each other’s company.

Alternative options
– Winter Club (ice skating rink) and Orlando Ice (ice skating rink)

Wine Tasting at The Wine Room

For wine-loving couples, a wine tasting at The Wine Room is the perfect date night activity. Explore a variety of wines from around the world in a cozy and inviting atmosphere. You can even pair your wine with delicious small plates for a complete dining experience.

Alternative options
– The Wine Barn (wine bar) and The Parkview (wine bar)

Stroll Through Park Avenue

Take a leisurely stroll down Park Avenue, Winter Park’s charming main street lined with boutiques, cafes, and art galleries. Browse the shops hand in hand, stop for a cup of coffee or gelato, and soak in the vibrant atmosphere of this bustling district.

Alternative options
– Hannibal Square (historical district) and Morse Museum (art museum)

Couples Massage at The Spa at the Alfond Inn

Indulge in some pampering together with a couples massage at The Spa at the Alfond Inn. Relax and unwind as skilled therapists work out the tension in your muscles, leaving you both feeling rejuvenated and refreshed.

Alternative options
– Spa at The Ritz-Carlton Orlando, Grande Lakes and The Woodhouse Day Spa

Sunset Boat Tour on Winter Park Chain of Lakes

Experience the natural beauty of Winter Park from a different perspective by taking a sunset boat tour on the Winter Park Chain of Lakes. Enjoy the peaceful serenity of the water as you watch the sun set over the horizon with your loved one by your side.

Alternative options
– Scenic Boat Tour (boat tour) and Winter Park Boat Tours (boat tour)

Live Theater at The Winter Park Playhouse

For a night of entertainment and culture, catch a show at The Winter Park Playhouse, Central Florida’s only professional musical theater. Enjoy a night of singing, dancing, and laughter as you watch talented performers bring the stage to life.

Alternative options
– Mad Cow Theatre (live theater) and Orlando Shakespeare Theater (live theater)

Art Gallery Hopping in Hannibal Square

Explore the vibrant arts scene in Winter Park by going on an art gallery hop in the historic Hannibal Square neighborhood. Admire local artwork, meet artists, and discover hidden gems as you wander from gallery to gallery with your partner.

Alternative options
– Albin Polasek Museum & Sculpture Gardens (art museum) and Crealdé School of Art (art studio)

Dessert Date at Better Than Sex

Indulge your sweet tooth with a dessert date at Better Than Sex, a romantic dessert bar known for its decadent desserts and intimate ambiance. Share a sinful treat like the “Between My Red Velvet Sheets” and savor every last bite.

Alternative options
– The Glass Knife (dessert shop) and Le Macaron French Pastries (pastry shop)

Cooking Class at Truffles & Trifles

Get hands-on in the kitchen together by taking a cooking class at Truffles & Trifles. Learn new culinary skills, experiment with different flavors, and enjoy a delicious meal that you’ve prepared together. It’s a fun and interactive date night idea that’s sure to bring you closer.

Alternative options
– Publix Aprons Cooking School (cooking school) and Chef’s Night at Second Harvest Food Bank (cooking class)

Now that you have a variety of date night ideas to choose from, all that’s left to do is book a babysitter through Wyndy and enjoy a well-deserved night out with your partner. Rediscover the magic of your relationship and create lasting memories together in Winter Park. Happy dating!