How Far in Advance Should You Book Holiday Party/Event Entertainment?

Every year, the same thing happens. Early December rolls around, the holiday party is all planned, the venue is booked, the snacks are ordered… and then someone remembers the entertainment.

By then? It can be slim pickings.

Whether you're planning a corporate holiday party, a school winter fun fair, or a festive get-together at home, here's how far in advance to book, and how to make sure you get the date you want.

The Short Answer

• Most of the year: book at least 4 to 6 weeks ahead

• Holiday season (late November to December): book at least 6 to 8 weeks ahead

That means if you're planning a holiday event, the best time to book is right now. The most popular dates are already filling up.

Why Holiday Dates Go So Fast

The holiday season packs a lot of events into just a few weeks. Corporate holiday parties, school fun fairs, holiday markets, community events and family celebrations all land on the same handful of dates.

And almost everyone wants the same thing: a weekend.

Saturdays and Sundays in late November and December are the hot spots, and they're always the first to go.

Where to Find Flexibility

If your weekend date is already booked, or you're starting late, look at weekdays:

• Weekday daytime events (school events, daycare parties, office celebrations) usually have the most availability

• Weekday evenings can also have more openings than weekends

If your event has any wiggle room on the date or time, let us know when you reach out. A small shift can be the difference between "fully booked" and "you're in."

Booking Specialty Services? Give Yourself Extra Time

Face painting, glitter tattoos and balloon animals are our most popular services, and we have the most entertainers trained for them.

Specialty services are a different story. These include:

• Caricatures

• Slime stations

• Active games, LEGO and challenges

• Craft stations

These services take specialized skills, supplies and prep, so there are fewer entertainers available for each one on any given day. When a few December Saturdays fill up, those spots are gone.

If you have your heart set on a specialty service, book it as early as you can, ideally 8 weeks or more before your holiday event.

Know Your Numbers (As Best You Can)

We know, guest counts are tough to pin down weeks ahead, especially for corporate events and holiday markets. But having a rough idea of how many kids you're expecting helps us recommend the right number of entertainers and the right amount of time.

A few ways to estimate:

• Private parties: use your invite list or early RSVPs

• Corporate events: look at last year's attendance or the number of employees with kids

• Public events: use past turnout and the size of your space

For reference, one face painter can paint about 17 to 20 kids per hour with basic designs. (Here's the full breakdown.)

It's Always Better to Overbook Than Underbook

This is one of the biggest lessons we've learned over the years.

If you underbook, you end up with long lines, frustrated parents, and kids who don't get a turn. Once a child has been promised face painting, it's very hard to walk that back.

If you overbook? Nobody's sitting around twiddling their thumbs. If we have extra time, we'll:

• Do more detailed designs

• Let kids come back for additional face paint or glitter tattoo

• Make extra balloons so kids can take home more than one

Extra time always turns into a better experience for your guests.

How Booking Works Behind the Scenes

1. Start with our booking form

The best way to check availability is through our Check Availability & Get a Quote form. It gives us everything we need to put together your quote quickly.

2. Why there's no live calendar online

We get this question a lot! You won't find a real-time availability calendar on our website, and that's on purpose.

There's a lot happening behind the scenes: matching entertainers to events, juggling travel across the GTA, holding dates while clients confirm details, and working out timing with venues. Our calendar changes by the hour during the holiday season, so the most accurate answer always comes from reaching out directly. For the quickest response, you can call or email us directly.

3. Your date isn't locked in until the deposit is paid

This is the big one. Entertainment is booked on a first come, first served basis, so your date is officially confirmed once your deposit is paid (or once you've made an arrangement with us to pay in full instead).

A quote alone doesn't hold your spot. During the holidays, we sometimes have more than one inquiry for the same date and time, and the first deposit secures it.

4. Don't have every detail yet? That's okay

You don't need to have it all figured out to get on the calendar. We've worked with companies who knew their date and time but hadn't confirmed a venue yet, and that's totally fine.

Lock in the date first, and send the rest of the details as they come together. Just keep in mind that travel fees depend on your final location.

What to Have Ready When You Reach Out

The more we know upfront, the faster we can confirm your quote. Here's a quick checklist:

• Event date and start and end time

• Location (or at least the postal code, if your venue isn't confirmed yet)

• Estimated number of kids, and their age range

• Services you're interested in

• Indoor or outdoor (for winter events, here's why an indoor spot matters)

• Any extras your venue requires, like a certificate of insurance or parking details

A Quick Note for Corporate Clients

Corporate bookings often need internal approvals, purchase orders, or venue paperwork before anything is confirmed. Build that time into your timeline. If approvals usually take a couple of weeks at your company, start the conversation with us even earlier.

Final Thoughts

The holidays are one of the busiest times of the year for kids entertainment in Toronto and the GTA. A little planning goes a long way.

Quick recap:

• Book 6 to 8 weeks ahead for holiday events

• Weekends go first, so stay flexible on weekdays if you can

• Give specialty services an even bigger buffer

• Overbook rather than underbook

• Your date is confirmed once your deposit is paid

At All The Craze Entertainment, we bring face painting, glitter tattoos, balloon animals, slime stations, LEGO building and more to holiday parties, corporate events and school fun fairs across Toronto and the GTA.

Check availability and get a quote to get on the calendar.