The Company Holiday Party Planning Checklist
By Jordan Zarcone, Director of Sales
Every year, without fail, it happens.
Someone floats the idea in a Slack message or a Monday morning meeting. "We should do something really fun for the holiday party this year." Everyone agrees enthusiastically. And then life happens, Q4 gets busy, and suddenly it's mid-November, and you're scrambling to find a venue that isn't already booked solid.
I've seen it play out more times than I can count. And every time, the stress is the same. Too many decisions, not enough time, and a team that deserves better than a last-minute banquet room with a sad cheese plate.
Here's the checklist I walk our clients through every year as they plan private events at Rally, and it makes the process feel less like a second job and more like the fun thing it's supposed to be.
Start With the Date
Everything else flows from this. Pick a date, or at least a window, before you do anything else.
Prime holiday dates go fast. Thursdays, Fridays, and Saturdays in December are the first to disappear and they go earlier than you'd think. If your team has a preference, get it on the calendar as soon as you have internal buy-in.
One thing worth knowing: weekday availability is often more flexible and can open up options you wouldn't have otherwise, including some breathing room in your budget.
Get a Rough Headcount
You don't need a final guest list. You need a ballpark.
Planning for 20 people looks completely different from planning for 200. Your headcount shapes everything — the space, the food and beverage package, the activities, and how the night flows. Start with your best estimate and refine as you get closer. Nobody expects you to have it all figured out in September.
Decide What Kind of Party You Want
This is the most important question and the one most people skip straight past.
Before you think about menus or spaces or details, think about how you actually want your team to spend the evening. Not what sounds impressive on paper. What sounds like them.
There's a whole spectrum of options:
Social and relaxed. Cocktails, good food, and plenty of time to just be people together. No agenda, no icebreakers.
Interactive and casual. An activity that gives everyone something to do without making the whole night feel like a structured team-building exercise.
Competitive and high-energy. Organized gameplay, a tournament bracket, and bragging rights that last until next December.
All of the above. Gameplay, cocktails, dinner, and enough room in the schedule to breathe.
At Rally, that could mean a Pro-Led Tutorial for a quick intro to pickleball, a Mixer for casual rotating play, or a full Rally Scramble or Custom Tournament for teams that take friendly competition seriously. If you’re planning a corporate outing, there's no wrong format. The best holiday party is the one that actually feels like your team.
Match the Space to Your Group
Once you know your headcount and event vibe, finding the right space gets a lot easier. The goal is enough room for everyone to feel comfortable without so much space that the energy gets lost.
At Rally, the options scale with your group:
Garden Pods or Cocktail Bar — Intimate and conversation-friendly for groups up to 50.
The Paddle Room — Semi-private lounge seating with TVs and optional ping pong for up to 50 guests.
The Lawn + Fire Pits — Open air with gas fire pits for up to 150 guests. Nothing says holiday party like a fire pit and a drink in hand.
4 Outdoor Courts + Lounge — Up to 84 guests with courtside lounge seating.
Main House Buyout with 4 Indoor Courts + Lounge — The full Rally experience for up to 500 guests. The holiday party that takes over the whole venue.
Find the space that fits your group and the rest falls into place.
Build Your Food and Beverage Experience
Food and beverage isn't an afterthought. It's half the party.
Think about the overall experience first. Passed bites and cocktails? A more substantial spread? A seated dinner? A combination of stations and an open bar? Once you have a direction, think about the details that make it feel curated. A seasonal cocktail on arrival, a specialty station, a festive enhancement that makes the menu feel intentional rather than generic.
And yes, a spiked hot cocoa bar is always a good idea. I'll stand by that one.
Add the Details That Make It Feel Like a Party
The big decisions are done. Now comes the fun part.
A few thoughtful touches go a long way. Company branding or custom signage, team awards or prizes, a DJ or a really good playlist, holiday-themed cocktails, a photo moment, a tournament format that gives people something to root for. None of these have to be complicated. The ones that land are usually the simplest — the detail that makes someone say "wait, they actually thought of that."
Hand It Off and Show Up
This is the part people forget to plan for: the moment you stop planning and actually enjoy the party.
Once the date, headcount, format, space, menu, and beverage package are locked in, my team takes it from there. We handle the logistics, the setup, the coordination, and the details so that when your team walks in the door, everything is ready and you can actually be present for the night you spent months putting together.
Your job on party day? Show up, grab a drink, cheer on your coworkers, and let us handle the rest.
Your Holiday Party Planning Timeline
8+ weeks out: Lock in your date and estimated headcount. Seriously, do this first.
6 weeks out: Choose your event format, space, and overall experience.
4 weeks out: Finalize food, beverage, entertainment, and any enhancements.
2 weeks out: Confirm your final guest count, timeline, and event details.
Party day: Show up. We've got it from here.
Ready to Get Started?
The holidays are busy enough without adding a full event planning project to your plate. Tell us your group size, preferred dates, and vision, and we'll build something around it. Space, activities, food, beverage, all of it.
Whether you're planning an intimate team dinner, a competitive pickleball tournament, or a full venue buyout, my team has the space and the experience to make it happen.
If you’re ready to start planning your holiday party, reach out to me directly or fill out this form, and we’ll take it from there.
Planning a November event? We're offering complimentary perks for events booked and contracted by October 31st. Learn more about the November incentive here.