How to Plan Your December for a Meaningful, Stress-Free Holiday Season
Plan December the way you’d plan a trip — with space for the things that make it meaningful
December can be busy and go by quickly. With school events, work deadlines, guests, and last-minute errands, your calendar is full before you know it. By the time January comes around, it can feel like you never had a break.
This post shows you how to stop reacting and start planning. Think of December like a trip — you have a set number of days, a few must-do stops, and a chance to make choices about how you spend the rest. When you plan it like you’d plan a trip, you can build a month that works for you.
Before you start, grab a piece of paper or open your calendar — the goal is to walk away with a plan you can use right away.
Step 1: Decide What You Want This Month to Feel Like
Pause before you fill the calendar and write down how you want this December to feel.
Before you open the calendar, pause and write down a few quick answers. This helps you figure out what you want out of December before you start filling every day.
Quick Check-In:
This December, I want my days to feel:
Calm and cozy
Packed with activities
Somewhere in the middle
Hosting or having guests makes me feel:
Excited to plan things for everyone
Like I need to keep it simple
Like I want space for myself
If everyone remembers one thing about this holiday, I want it to be:
Example: “I want December to be about connecting with my family — a few planned activities, time for rest, and space for unplanned fun.
This is like deciding the purpose of a trip — before you pick flights, you figure out if the goal is adventure or rest.
Step 2: Mark Your Non-Negotiables
Step 2: Write down the dates you already know — guests, school events, and deadlines — so you can plan around them.
Look at your calendar and write down:
Guest arrival and departure dates
School concerts, recitals, or sports games
Work events or deadlines
These are the events you’ll plan around.
Example: Guests Dec 21–26, school concert Dec 18, office party Dec 10.
This is like putting flights and hotel bookings on your itinerary before you add anything else.
Step 3: Choose What You Actually Want to Do
Step 3: Pick one or two things per category — outings, at-home activities, meals, and reset moments — to make your month feel special without overloading it.
Instead of trying to do everything, choose one or two things per category. The lists below are suggestions — feel free to add your own ideas that fit your family, guests, and schedule.
Step 3: Choose one or two things per category — outings, at-home activities, meals, and reset moments — and keep it simple so you can enjoy them.
Step 4: Put It on the Calendar
Step 4: Add your chosen activities to your calendar — and block time for prep — so they actually happen.
Take five minutes and add what you picked to your calendar. Block time for prep if you need it.
Example: Block Dec 22 from 3–5 PM for cookie bake. Block Dec 23 evening for lights drive.
This is like adding excursions to a travel itinerary — it locks them in and keeps other commitments from pushing them aside.
Step 5: Look Back Before the Month Ends
Take five minutes to look back on what worked and what didn’t this December — and plan next year’s holidays with less stress and more meaning.
When December is over, take a minute to jot down:
What worked this year?
What felt like too much?
What memory do I want to repeat next year?
This will make planning next December faster and easier.
Why This Matters
Pause and enjoy the small, meaningful moments this season — that’s what all the planning is for.
When you finish these steps, you have a plan that matches your priorities.. You’ve left space for what matters, protected time to relax, and added at least one thing just for you.
This is what Trip Planning Your Way looks like. You’ve treated December like a destination and made choices that fit how you want to experience it.
Download the Worksheet
Download the free printable worksheet to walk through these steps and plan your December.
To make this even easier, I created a one-page worksheet you can print and fill out. It walks you through these five steps, with space to write your answers, pick your activities, and add them to your calendar.
[Download Your December Planning Worksheet]
Pin it, save it, or print it — and use it again next year.
Want more info about travel planning your way? Check out How to Plan a Trip that Matches Your Travel Style. Interesting in smart packing or styling tips click here for packing and here for style.
