Episode #15: How to Travel During the Holidays With Kids: Keeping Christmas Traditions Alive Anywhere

“Can you travel during the holidays — Thanksgiving or Christmas — and STILL have it feel like home?”

Short answer?
Yes. Absolutely. With a little intention and a little parent magic.

Whether you're traveling to see extended family or taking a big family vacation somewhere tropical, snowy, or totally new — you can keep your traditions alive, make meaningful memories, and still have the holiday spirit, even if you’re thousands of miles away.

And today, I’m sharing exactly how we do that — including our big Christmas trip to Puerto Rico with 12 people, what worked, what I worried about, and all my best tips to help you create a holiday that feels just as magical even when you’re not at home.

Let’s get started.

🎄 PART 1: Our Christmas in Puerto Rico — The Backstory

In 2023, we had one of the most memorable Christmases ever…
Christmas in Puerto Rico.

• My mom had always dreamed of doing a big family Christmas trip

• She rented a huge Airbnb for 12 of us — our family, my mom, and my sister’s family

• All we had to do was get ourselves there — so we flew on Southwest points

But I’ll be honest…
I was nervous.

I had all the typical mom thoughts:

• “Will it feel like Christmas?”

• “Will my kids miss being home?”

• “How do I keep our traditions alive in a rental house?”

• “What about Santa?!”

But this trip ended up being one of the MOST magical holidays we’ve ever had, and I learned so much about creating Christmas anywhere.

🎄 PART 2: How I Made Christmas Feel Like Christmas (Even in Puerto Rico)

1. I packed small but meaningful gifts

I didn’t go overboard — because honestly, the TRIP was part of the gift.
My strategy:

• 2 gifts per kid

• Stocking stuffers

• “Santa still found us in Puerto Rico” magic ✨

But manageable luggage-wise.

2. I brought a “mini Christmas tree”

This was genius and SO easy.

• A felt Christmas tree (flat, lightweight, packable)

• A small set of battery or plug-in lights

• Command hooks to hang it on the wall

It instantly transformed the Airbnb and gave us that cozy Christmas vibe we needed.

3. We kept our core Christmas Eve traditions

No matter where we are, we ALWAYS:

• Open Christmas pajamas on Christmas Eve

• Decorate cookies

• Play games as a family

• Read a Christmas story

These traditions anchored the whole day and made everything feel familiar.

4. Simple grocery pickup = holiday magic

We placed a pickup order with:

• Cookie decorating kits

• Breakfast ingredients

• Hot cocoa

• Snacks for Christmas Day

• Easy family meals

This kept the stress low and kept traditions intact.

5. And then… we went to the BEACH for Christmas afternoon

And honestly?
It was incredible.
Warm, beautiful, and such a fun twist on Christmas Day.

A reminder that:
Traditions don’t have to die… they just evolve.

🎄 PART 3: Spending Christmas in Tulsa

Every few years, we also spend Christmas in Tulsa, Oklahoma with my husband’s family.

And even though it’s not tropical, it’s still not home, and the same principles apply:

• Bring your core traditions with you

• Blend your traditions with the traditions of the family hosting

• Give kids consistency but also let them enjoy the uniqueness of being somewhere different

• Keep expectations flexible

We do:

• Matching PJs

• Cookie decorating

• Christmas Eve activities

• Family games

• Stockings

• Gifts

But we also let the kids enjoy cousin chaos and whatever traditions Greg’s family does.

It’s a mix, and that’s what makes it special.

🎄 PART 4: Tips for Traveling for Christmas (or Any Holiday)

Here are practical tips families can use anywhere:

1. Identify your “non-negotiable traditions”

Ask yourself:
What makes it FEEL like Christmas for us?

Maybe it’s:

• Christmas jammies

• A certain meal

• Stockings

• A story

• A movie

• A special breakfast

Keep 2–5 of these alive and let the rest be flexible.

2. Pack light but meaningful holiday items

Ideas:

• Felt tree

• Stockings

• Battery-powered candles

• Small string lights

• Family Christmas PJs

• A Christmas book

• A holiday playlist downloaded offline

• Cookie-decorating supplies

• A small advent calendar

These take up very little space but create HUGE holiday vibes.

3. Plan simple, travel-friendly gifts

Try:

• Experience gifts

• Travel-friendly gifts (books, games, crafts)

• Smaller toys that fit in a suitcase

• Digital gifts

Kids don’t need a living room full of gifts to feel the magic.

4. Set expectations ahead of time

Tell kids:

• “Christmas will look a little different this year, but that’s what makes it special.”

• “We’ll still do our favorite traditions, just in a new place.”

• “Santa knows where EVERY kid is sleeping, anywhere in the world.”

Kids do great when they know what to expect.

5. Grocery pickup = lifesaver

Order ahead:

• Breakfast

• Snacks

• Cookie kits

• Christmas Eve dinner

• Christmas morning treats

Make the Airbnb feel like home with familiar foods.

6. Blend traditions — don’t force “home Christmas”

If you're with extended family:

• Let the kids join their cousins’ traditions

• Share your traditions

• Create new ones together

Holidays evolve — and that’s beautiful.

7. Build in downtime

Travel + holidays = overload
Kids NEED:

• Rest

• Quiet time

• Buffer time

Don’t overschedule your trip.

8. Don’t underestimate the magic of being somewhere new

Christmas morning somewhere unexpected?
Unforgettable.

🎄 PART 5: Holiday Travel Checklist

✔️ Choose 2–5 core traditions to bring with you
✔️ Pack stockings
✔️ Bring simple decorations (felt tree, lights)
✔️ Pack PJs & Christmas outfits
✔️ Bring 1–2 small gifts per kid
✔️ Pre-order groceries for pickup
✔️ Bring cookie-decorating items
✔️ Download holiday playlists or movies
✔️ Bring a travel-friendly game or puzzle
✔️ Prep kids for what Christmas will look like
✔️ Keep the schedule simple
✔️ Add a festive “surprise” moment (treat, outing, beach, lights, etc.)