Dinner and a Movie

Start your date night off with a classic dinner and a movie. Winter Garden is home to a variety of restaurants offering delicious cuisine, such as Market to Table Cuisine, Chef’s Table at the Edgewater, and Winter Garden Pizza Co. After dinner, head to the Garden Theatre for a movie screening. Alternative options: Plant Street Market, The Whole Enchilada, Moon Cricket Grille.

On-Demand Childcare in Your Neighborhood

Book a Sitter

Wine Tasting at a Local Winery

Spend a romantic evening tasting locally crafted wines at the Winter Garden Winery. Learn about different flavors and varieties while enjoying each other’s company in a cozy setting. Alternative options: Quantum Leap Winery, The Wine Barn, Lakeridge Winery & Vineyards.

Couples Painting Class

Unleash your creativity together at a couples’ painting class. Sip on your favorite drinks as you create a masterpiece side by side. It’s a fun and unique way to bond with your partner. Alternative options: Paint Nite at local bars, Painting with a Twist, Corks and Brushes.

Stroll Through Historic Downtown

Take a leisurely walk through historic downtown Winter Garden. Explore the charming streets, visit local shops, and admire the historic architecture. Enjoy an ice cream cone or a cup of coffee as you soak in the ambiance. Alternative options: Winter Garden Heritage Museum, Heritage Museum Farmers Market, Garden Theatre.

Live Theater Performance

Catch a live theater performance at the Garden Theatre. Enjoy a night of entertainment and culture with your partner as you watch talented actors and musicians perform on stage. Alternative options: Orlando Shakespeare Theater, Mad Cow Theatre, Dr. Phillips Center for the Performing Arts.

Ice Skating at the RDV Sportsplex

Embrace the winter season by going ice skating at the RDV Sportsplex Ice Den. Hold hands as you glide across the ice and enjoy a playful and active date night. Alternative options: Amway Center, Light Up UCF, Winter Park Ice Skating Rink.

Cooking Class for Couples

Learn a new skill together by taking a cooking class for couples. Enjoy a hands-on cooking experience as you work together to create a delicious meal. It’s a fun and interactive way to spend quality time with your partner. Alternative options: Truffles and Trifles, Puff ‘n Stuff Catering, Publix Aprons Cooking School.

Evening Picnic at Lake Apopka

Pack a picnic basket and head to Lake Apopka for a romantic evening under the stars. Enjoy a meal together as you overlook the serene lake and bask in the tranquility of nature. Alternative options: Lake Eola Park, Kraft Azalea Garden, Lake Louisa State Park.

Sunset Boat Tour on Lake Butler

Embark on a sunset boat tour on Lake Butler for a peaceful and romantic experience. Watch the sun dip below the horizon and enjoy the tranquility of the water as you cruise along with your partner. Alternative options: Dinky Dock Park, Winter Park Scenic Boat Tour, Lake Baldwin.

Pampering Couples Spa Day

Indulge in a relaxing and rejuvenating couples spa day. Pamper yourselves with massages, facials, and other treatments designed to help you unwind and de-stress. It’s a luxurious way to bond and enjoy each other’s company. Alternative options: The Woodhouse Day Spa, The Spa at Rosen Centre, Orchid Spa and Wellness.

If you’re a parent in need of a night out, Wyndy is here to help! We connect families with trusted, background-checked Wyndys in their area who are available to provide childcare services. Hire a Wyndy for your next date night and enjoy some quality time with your partner. Book now at wyndy.com.