Date Night in Orlando: How to Actually Enjoy It When You Have Kids

You planned the trip for months. You booked the flights, the hotel, the park tickets. You even made a dinner reservation at one of those restaurants you have been saving on Instagram since 2023. And then reality sets in: you have kids, you are in a city where you do not know anyone, and the idea of leaving them with a stranger in a hotel room makes your stomach turn.

So you skip the dinner. Again.

If this sounds familiar, you are not alone. Most parents visiting Orlando with young kids never actually get a night out together. The logistics of finding trustworthy childcare in a city you are just visiting for a week feels like more trouble than it is worth. But it does not have to be that way.

The Real Problem with Date Night on Vacation

At home, you have options. Grandparents, your neighbor, the teenager down the street you have known since she was ten. On vacation in Orlando, your options shrink to hotel concierge referral services and apps full of people you have never heard of. The trust factor drops and the prices climb.

Standard hotel babysitting services in Orlando run $18 to $25 per hour per child with a four-hour minimum. For a family with two or three kids, that adds up fast. And you are still handing your children to someone you have never met, with no character, no entertainment, and no way to make the kids feel good about the arrangement.

The result? Most parents eat room service after the kids crash and call it a night.

What If the Kids Were Excited for You to Leave?

Imagine telling your four-year-old that while you and your partner go to dinner, a real princess is coming to the room to spend the whole evening with them, hang out in character, and stay all the way until bedtime.

That is what a princess babysitter does. A vetted, background-checked sitter shows up dressed as your child's favorite princess character, fully in role, and ready to take care of your kids for the evening. Your kids are not just okay with you leaving. They are practically pushing you out the door.

Princess babysitting solves both problems at once: parents get trustworthy, vetted childcare they can feel good about, and kids get an experience that becomes one of the highlights of the entire trip.

Where to Go for Date Night in Orlando

Once the childcare question is handled, Orlando actually has an incredible dining and entertainment scene that most family tourists never see.

For a nicer dinner, Victoria and Albert's at the Grand Floridian is the ultimate Orlando fine dining experience. Capa at the Four Seasons offers rooftop steakhouse vibes with fireworks views. For something more casual but still excellent, The Ravenous Pig in Winter Park is a local favorite that lives up to the hype.

For a fun night out, ICEBAR Orlando is a completely ice-built bar and lounge that makes for a memorable experience. The Wheel at ICON Park gives you a different view of the city. Disney Springs has a solid lineup of restaurants and bars that do not require park tickets.

For something low-key, a walk around Disney Springs can be surprisingly relaxing without kids in tow. Winter Park's Park Avenue has great wine bars and boutiques with an atmosphere that feels a world away from the theme parks.

How to Book a Princess Babysitter in Orlando

Visit enchantedchildcare.com and browse the available princess characters. Pick the one your child is most obsessed with (or let them choose, which is half the fun). Select your date, time, and location. Add any extras like an additional hour or a second character for bigger groups.

The sitter arrives in character, checks in through the platform, and sends you updates throughout the evening. You get a real night out. Your kids get a night they will talk about for the rest of the trip.

We also offer superhero babysitters if your kids prefer capes over tiaras. Check out our superhero characters to see the full lineup.

Have questions about how it works? Check out our FAQ page for everything you need to know about pricing, safety, and the booking process.

It Is Worth It

Parents consistently say that the princess babysitter booking was one of the best decisions of their Orlando vacation. The kids get an unforgettable experience, and the parents get something they rarely allow themselves: a few hours to just be a couple again.

If you are planning an Orlando trip and debating whether to book a sitter, do it. Your kids will thank you. And honestly, you will thank yourself.