Romantic Dinner at Eleven Rooftop Restaurant

Experience fine dining at its best at Eleven Rooftop Restaurant, located at the Reunion Resort. Enjoy panoramic views of the city skyline and indulge in delicious dishes prepared by top chefs. The elegant ambiance and impeccable service make Eleven a perfect spot for a romantic date night.
Alternative options: Bull & Bear Steakhouse, Capa at Four Seasons Resort Orlando

On-Demand Childcare in Your Neighborhood

Book a Sitter

Salsa Dancing at Cuba Libre Restaurant & Rum Bar

Put on your dancing shoes and head over to Cuba Libre for a night of salsa dancing and Latin-inspired cocktails. The lively atmosphere and energetic music make this restaurant a great place to let loose and have some fun with your partner.
Alternative options: Mango’s Tropical Cafe, Rocco’s Tacos and Tequila Bar

Hot Air Balloon Ride with Thompson Aire

Experience Kissimmee from a bird’s eye view with a hot air balloon ride with Thompson Aire. Float above the city and enjoy breathtaking views of the landscape below as you and your partner create lasting memories together.
Alternative options: Orlando Balloon Rides, Magic Sunrise Ballooning

Wine Tasting at Island Grove Winery at Formosa Gardens

Sample a variety of wines at the Island Grove Winery and learn about the winemaking process. This picturesque winery offers a relaxing setting for a romantic evening of wine tasting and conversation with your loved one.
Alternative options: Quantum Leap Winery, The Wine Room

Bowling at Splitsville Luxury Lanes

Put a fun twist on your date night with a friendly game of bowling at Splitsville Luxury Lanes. Enjoy delicious food, refreshing drinks, and upbeat music while you and your partner compete for the winning score.
Alternative options: Kings Dining & Entertainment

Live Theater Show at the Osceola Arts

Catch a live theater performance at the Osceola Arts and immerse yourself in the world of drama, music, and dance. From classic plays to contemporary productions, there’s something for every theater enthusiast to enjoy on a date night out.
Alternative options: Mad Cow Theatre, Dr. Phillips Center for the Performing Arts

Couples Spa Day at Relache Spa

Indulge in a day of pampering and relaxation with your partner at Relache Spa. Treat yourselves to a couples massage, facial, or body treatment, and unwind in a tranquil oasis away from the stresses of everyday life.
Alternative options: The Ritz-Carlton Spa Orlando, The Spa at Celebration

Nighttime Safari at Wild Florida

Embark on a nighttime safari adventure at Wild Florida and get up close and personal with exotic wildlife in their natural habitat. From nocturnal animals to thrilling airboat rides, this unique date night experience will leave you awe-struck.
Alternative options: Gatorland, Central Florida Zoo & Botanical Gardens

Stroll Around Old Town Kissimmee

Take a leisurely stroll around Old Town Kissimmee and discover charming shops, restaurants, and entertainment venues. Enjoy live music, classic car shows, and delicious food as you and your partner explore this quaint area together.
Alternative options: Celebration Town Center, Disney Springs

Sunset Cruise on Lake Tohopekaliga

Embark on a romantic sunset cruise on Lake Tohopekaliga and admire the stunning views as the sun sets over the water. Whether you choose a private boat tour or a group excursion, this peaceful and scenic setting is perfect for a romantic date night with your partner.
Alternative options: Spirit of the Swamp Airboat Rides, Boggy Creek Airboat Adventures

As a parent, finding time for a date night can be a challenge, but it’s important to prioritize your relationship and spend quality time with your partner. Wyndy makes finding a reliable and trustworthy babysitter easy, so you can enjoy a night out knowing that your children are in good hands. Book a Wyndy babysitter today and make your date night in Kissimmee one to remember.