This post is part of the 100 Days ’til Christmas Challenge — one small step each day to make the holiday season less stressful and a lot more fun.

“Mid-century Christmas illustration, overhead view of a December planner open to a calendar page, surrounded by ornaments, ribbon, pine branches, candy canes, and a steaming mug of cocoa, warm vintage colors, soft shadows, no hands or people, subtle festive sparkle, room for text overlay, #100DaysTilChristmasChallenge, title text included.”

Every year I look at the calendar and think, “We’ve got plenty of time. Twenty-five whole days.” And then December shows up with school events, work deadlines, family traditions, errands, and all the little things we forget to account for.

Today is a perfect moment to pause and do a bit of December holiday planning—the kind that keeps your month feeling calm instead of chaotic. Not a full reset. Not a big to-do. Just a simple check-in to make sure the things you want to do have an actual place in your real-life schedule.

Let’s get everything lined up before December gets loud.

Look at Your December Calendar With Fresh Eyes

Pull out the holiday calendar you set up back on 99 Days ’Til Christmas. All the major plans should already be there, so today’s task is simply a quick December check-in.

Start by double-checking dates, times, and details for everything you previously added:

This part is fast, but it’s an important piece of your overall December holiday planning because schedules shift, reminders get missed, and it’s so easy to overlook those tiny details that cause stress later.

Now look for your true windows.

Once everything is confirmed, take a step back and notice what’s left:
the small pockets of time where you actually have space to do things like:

  • finish a handmade gift
  • bake cookies
  • plan a family fun night
  • enjoy a simple craft
  • or take a much-needed quiet evening

These “open days” are the heart of your December holiday planning. And most of us discover we have far fewer of them than we thought.

Revisit the Prep Work You’ve Already Done

One of the best parts of this 100-day challenge is that you’ve already done so much work leading up to this moment. Today is simply about placing those pieces on the calendar.

Handmade Gifts (94 Days)

Check your progress.
What’s done? What needs time?
Assign realistic finishing days now—don’t leave these floating in your head.

Holiday Crafts (87 Days)

Pick the 1–2 crafts you actually want to do this year.
Not every idea. Not every Pinterest project.
Just the ones that still sound fun.
Then match them to your open days.

Cookie & Baking Plans (90 Days)

Choose your baking days now so they don’t get squeezed out.
You can even prep dough early if you want to lighten the load.

Family Traditions & Activities

Think back to:

Which ones feel right for December?
Put those on your calendar before anything else fills that space.

Christmas Cards

You’ve already built your foundation with:

Schedule your final steps and choose your mail-by date.

Shopping Tasks

Reference what you did on:

Pick 1–2 focused shopping days, plus a backup day for returns or last-minute errands.

Decorating

If anything from 27 Days: Decorating Day still needs attention, schedule it.
Even small tasks also deserve a spot in your December holiday planning so you’re not scrambling.

Plan December Family Fun (Without Overloading Yourself)

This part is all about choosing with intention.

Pick your Top 3 family memories for the month—just three:

  • movie night
  • looking at lights
  • decorating cookies
  • a board game night
  • a simple craft afternoon

Then place them into your open windows.
These become your anchor moments—the ones that make the month feel magical even if everything else gets busy.

Final December Calendar Check-In

Before you close your planner, ask:

  • Does this schedule look doable?
  • Does it reflect what you actually want this month to feel like?
  • Is there anything that needs to move, shrink, or disappear altogether?

Make space for downtime, rest, and the slow moments that make December feel warm and peaceful.
That’s the “ease” this whole December holiday planning process is meant to create.

Want the Holiday Printables? Get Them All Free

If you haven’t grabbed the holiday printables yet — things like the holiday calendar, wishlists, gift lists, card trackers, Advent planning pages, and more — you can get all of them free when you join my newsletter.

You’ll get instant access to the full Holiday Hub, plus everything we’ve already used throughout this 100-day challenge. It’s the easiest way to stay organized without hunting for links each day.

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    Daily To-Dos

    • Open your December calendar
    • Double-check times and commitments
    • Identify your true open days
    • Choose and schedule your Top 3 family fun moments
    • Assign days for handmade gifts
    • Add baking days
    • Plug in any crafts
    • Delete anything that feels like too much

    Your December holiday planning doesn’t need to be perfect.
    It just needs to be intentional enough to keep the month feeling grounded and manageable.

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    Mom of 3, taxi service, logistics coordinator, meal planner, cook, and lover of cookies.