What to Expect on Your First Princess Babysitting Booking
You found Enchanted Childcare, you picked your princess, and you're about to book your first session. Now comes the question almost every parent asks before that first time: what actually happens?
Here's a full walkthrough of how a princess babysitting booking goes from start to finish, so you know exactly what to expect and your kids get the most out of it.
Before the Booking: A Few Things to Have Ready
Once your booking is confirmed, there's not much you need to do. But a couple of things make the experience smoother:
Let your kids know a special friend is coming to visit. You don't have to say who. The reveal is half the fun.
If you're in a hotel room, make sure the front desk knows to let your sitter up. Most Orlando hotels are used to this, but it saves a few minutes at arrival.
Think about which princess your child loves most. If your daughter is obsessed with Elsa, or your son can't stop talking about Rapunzel, that's worth noting at booking. We'll do our best to match it.
Have a general idea of bedtime. Your princess sitter will work toward it, but it helps to communicate it upfront so the evening has a natural arc.
Arrival: The Moment Your Kids Will Never Stop Talking About
Your princess sitter arrives in full costume, in character and ready to spend the evening with your kids.
For most kids, especially younger ones, this is a big moment. Some kids run straight toward her screaming. Some freeze in place, completely starstruck, and need a minute to process that their favorite princess just showed up at the door.
Both reactions are completely normal. Your princess sitter has seen both and knows how to meet your child where they are. If your kid needs a moment, she'll ease in gently with a warm royal greeting. If they're already mid-leap off the couch, she'll be ready for that too.
The Session: What Your Kids Actually Do
There's no set agenda, and that's intentional. Your princess sitter reads the room and builds the experience around your kids.
Most sessions include a mix of:
- Storytelling and imaginative play — tea parties, royal adventures, building ice castles, or exploring enchanted kingdoms (usually the biggest hit for the under-6 crowd)
- Arts and crafts if your family has supplies available — think princess crowns, magic wands, or royal drawings
- Singing, dancing, and movement for the kids who have energy to burn
- Quieter wind-down activities as bedtime approaches — gentle stories, lullabies, and calming princess rituals
The princess framing makes everything more engaging. Bedtime isn't bedtime. It's time for the royal family to rest before tomorrow's adventure. Dinner isn't dinner. It's a feast in the kingdom. Kids who normally resist both of those things tend to go along with it pretty willingly when a real princess is the one saying it.
Your Role: Actually Take the Night Off
This is the part parents sometimes struggle with, especially on a first booking. Your princess sitter is here to handle it. You don't need to hover, check in constantly, or feel guilty for stepping out.
If you're doing a date night, go have dinner. See a show. Take a walk. Your kids are with a background-checked, vetted sitter who genuinely loves working with kids. That's the whole point.
If you're staying in the same space (like a hotel suite), it's fine to be in the other room. You don't need to disappear entirely. Just give the princess room to do her thing and let your kids have the experience.
Bedtime: Where the Magic Really Earns Its Keep
Princess babysitting tends to shine at bedtime in a way that regular babysitting simply doesn't.
When a princess tells your daughter it's time for royal rest, or gently explains that the kingdom needs everyone well-rested for tomorrow's ball, kids listen in a way they sometimes don't when mom or dad says the same thing.
Your princess sitter will handle the full wind-down routine, whatever that looks like for your kids. Pajamas, teeth brushing, a bedtime story told in character. By the time you're back or ready to take over, they'll typically be settled or already out.
After the Session: What to Expect
When the booking wraps up, your princess sitter will give you a quick rundown of how the evening went. What your kids loved, how bedtime went, anything worth knowing.
Most parents report that their kids ask about the princess for days afterward. Don't be surprised if your daughter insists her new royal friend is a real, actual princess. For that night, she kind of was.
A Few Common Questions Before Your First Booking
What if my child is shy or nervous at first?
That's very common, especially for kids under 3. Princess sitters are trained to go at your child's pace. There's no pressure and no awkward forced interaction. A gentle curtsy, a soft hello, maybe a quiet compliment about something your child is wearing. Usually within 10 to 15 minutes, even the shyest kids have warmed up and are holding hands with their new princess friend.
What if my child doesn't recognize the princess?
Doesn't matter. Kids engage with the beautiful costume, the warmth, and the energy. You don't need to have a Disney-obsessed kid for this to work. The experience translates even if your child has no idea which princess showed up. A kind, sparkly, magical person who wants to play with them is exciting regardless.
Can siblings with different preferences be accommodated?
Absolutely. A princess sitter can host a royal adventure that includes everyone, regardless of age or interest. If one child loves princesses and another prefers something different, the imaginative play format is flexible enough to weave everyone into the story. You can also book a superhero sitter as a duo for families with mixed preferences.
How long does a typical booking run?
Standard bookings are 3 hours. That's enough time for a full arc: arrival and initial excitement, main activity time, wind-down, and bedtime. Extra hours are available if you need a longer evening.
Ready to Book Your First Princess Sitter?
Enchanted Childcare serves families throughout Orlando and Tampa, including hotel bookings near Disney World and Universal. If you're ready to give your kids a night they'll be talking about for weeks, join the waitlist and we'll be in touch.
Browse our princess characters to find the perfect match, or learn more about what a princess babysitter is and how character babysitting works.