Date Night, Without the Goodbye Negotiation
The hard part of date night is rarely the reservation. It is the ten minutes at the door. When the sitter arrives in costume, that part disappears, and you leave to a child who is already busy.
What does a date night booking include?
Three hours with your sitter for $199, covering up to three children. Extra hours are $50 each, so a longer dinner is a small step up rather than a new price tier.
She arrives a few minutes early, you hand over the essentials, and you go. Dinner, bedtime, and cleanup of whatever they made together are part of it.
Is three hours long enough?
For dinner nearby, usually. For dinner plus a show, plus parking, plus the drive, add an hour. Most parents underestimate this and then spend dessert watching the clock, which rather defeats the point.
Extra hours are cheaper than the anxiety. If you are unsure, book four.
What if my child has never had a sitter before?
This tends to be the easiest possible first sitter, because your child is meeting a character rather than a stranger. Tell us in the booking notes that it is their first time and mention what they love, and the sitter will lead with that.
It also helps to talk about it beforehand as something exciting that is happening, not as a thing you are doing to them. We wrote a short guide on preparing kids for a character sitter if you want the longer version.
Can we book the same sitter again?
Where availability allows, yes, and a lot of local families do exactly that. Familiarity is worth a great deal with younger children, and by the third booking the sitter knows your routines without being told.
Mention in your booking notes who you had last time and we will try to match it.
What does the sitter actually do while we are out?
Whatever your evening needs. Dinner, a craft, a movie, the bath, the story, the negotiation about one more story. She stays in character throughout, which is mostly what makes the routine parts go down easily.
Bedtime is the part parents care about most and the part the character helps with most. A four-year-old who will argue with you about pajamas will often not argue with a princess about them.
How do we know things are going fine?
You get a check-in message during the booking, so you are not sitting at dinner wondering whether to call. If anything comes up, your sitter contacts you directly.
Before every booking you fill in allergies, special needs, emergency contacts, and any instructions that matter, and your sitter reads all of it before she arrives. Nobody is improvising your child's peanut allergy at the door.
Which cities is this available in?
Orlando and Tampa, including the surrounding areas: Kissimmee, Lake Buena Vista, Celebration, Winter Park, Windermere, Winter Garden, and Lake Nona on the Orlando side, and St. Petersburg, Clearwater, Westchase, and Wesley Chapel around Tampa.
If you are visiting rather than local, the sitter comes to your hotel or vacation rental exactly the same way she would come to a house.
Common questions
How long is a babysitting session?
A standard princess babysitting session is 3 hours, which is included in the base rate of $199. You can add extra hours at $50 per hour per character. Most parents book for a date night, dinner out, or evening event.
How much does a princess babysitter cost?
A princess babysitting experience at Enchanted Childcare costs $199 for three hours with up to three children. You can add extra hours at $50 per hour per character, or add a second character for $149 if you have four or more kids or want a duo experience. With two characters, we can watch up to six children.
What ages is princess babysitting best for?
Princess babysitting is designed for children ages 2 through 10, though kids of all ages are welcome. Our sitters adapt their character energy and engagement style to the age group to keep every child happy and having fun.
Are your babysitters background checked?
Yes, every princess babysitter on our platform passes a comprehensive background check before their first booking. Sitters also complete a safety-focused platform orientation covering emergency procedures and childcare protocols. Your children's safety is our top priority.
How late can a date night booking run?
Late enough for dinner and an evening out, including the full bedtime routine. Add hours at $50 each when you book so your sitter is scheduled to stay as long as you need rather than watching the clock.
Do you take same-day date night bookings?
No. Bookings start from tomorrow, which gives us time to confirm a qualified sitter for your date and area. For a Friday night, book by Thursday at the latest.