If you’re prepared, you’re not scared – in this case, of a rocky family vacation. Whether this blog has found you before your spring break trip, your winter skiing excursion, or your first time out of the country with the family, welcome and settle in for the 9 most important skills I’ve learned for handling family vacations + printable packing lists to keep everyone organized and screen-free ways to pass the travel time.

Gearing up for a Calm(er) Family Vacation

Family vacations live in two places.

The dreamy version — sunlit mornings, children grateful and smiling, everyone wandering cobblestone streets together, and the whole family soaking up every single moment.

And the real version — someone can’t find their socks, someone packed three sweatshirts and no shorts, and you’re standing in the hallway wondering why this felt like a good idea.

After years of traveling with four kids (and 15 years producing large-scale events), I can tell you this:

A successful family vacation is built before you ever leave the driveway.

Not with perfection.
Not with pressure.

With systems that can turn your trip plans into a successful family vacation.

• 9 tips to prepare for your family vacation
• What actually makes a family vacation successful?
• 1 week packing list outlines + printable pdfs and my favorite can’t-leave-home-without item
• Screen-Free ways to pass the travel time
• Pin for your next family trip + see more of our travels

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9 Best Ways to Prepare for a Successful Family Vacation

You may remember my Top 10 Tips for “How to Stay Sane while Traveling with Kids” I’ve added a few notches to my belt since then but the tips there are just as applicable and a good addition to your travel planning!

1. Start With the Right “Why”

Before booking anything, we ask:

• Are we craving rest or adventure?
• Do we want nature or city?
• Do we need slow days or full days?

When we traveled to Italy, we knew it would be stimulating — more walking, more navigating, more newness. So we intentionally built in slower mornings and lighter afternoons.

You don’t eliminate chaos.
You plan with it in mind.

Clarity removes half the friction.

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2. When it comes to Booking, Choose Function Over Fancy

With a big family, square footage matters more than aesthetics.

Even in Italy — where beauty is everywhere — what mattered most was:

• A kitchen for simple breakfasts
• Enough beds that everyone slept well
• A place to regroup at the end of the day

When people can retreat, everyone behaves better.

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3. Simplify Packing (So You Can Think Clearly)

Packing is where most vacation stress begins.

Decision fatigue hits fast:

What if it rains?
What if they spill gelato?
What if we walk more than expected?

Over the years, we’ve simplified this a lot — and one thing that genuinely helps is using our Walker Family Roller Bags.

We love them because they’re structured and consistent. The compartments are predictable. The size is reasonable. The kids know what fits and where it goes.

And that structure quietly cuts the decision overload in half.

Instead of overpacking “just in case,” the bag sets the boundary.

If it fits neatly, it comes.
If it doesn’t, it doesn’t.

It’s not about the bag being magical — it’s about having a system that makes packing efficient and repeatable. (Sometimes, the girls and I will intentionally leave one of the smaller pouches empty in case we find a local thrift store and bring home a new outfit.) For us, these bags make trips like Italy possible because everyone can roll their own, manage their own things, and move through airports or train stations without me juggling six suitcases.

We genuinely appreciate how much simpler they make departure day. And simpler departure days change everything.

Use code Hearty15 for 15% off – we seriously love these suitcases!

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4. Pack in Outfit Bundles

Inside each bag, we:

• Roll complete outfits together
• Limit shoes to two pairs
• Share a family toiletry bag
• Bring one neutral layer per person

This keeps choices minimal but still flexible.

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5. Plan the First 24 Hours of the trip Carefully

The first day sets the tone — especially when traveling far.

When we landed in Italy, we didn’t overschedule. We walked, ate something simple, and got to bed early.

If the first evening feels calm, the rest of the trip usually follows.

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6. One Anchor Activity Per Day

We live by this rule:

One main activity per day.

A museum.
A market.
A bike ride.

Everything else is optional.

Over-scheduling drains everyone.
White space protects the joy.

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7. Everyone Contributes

Vacations don’t suspend family responsibility.

Each child:

• Manages their own bag
• Carries their own items
• Helps reset our space each night

Ownership builds confidence.
And it keeps resentment low.

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8. Expect Imperfection

Someone will be tired.
Someone will breathe on someone else without permission.
We may have to spend the night in the Chicago airport.

That doesn’t mean the trip failed.

A successful vacation isn’t flawless. And the minute we leave home, the adventure begins!

It’s prepared.
Flexible.
Shared.

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9. When One Grumpy Kid Threatens to Ruin the Vacation: The One Sentence That Saves the Day

Traveling with kids isn’t always sunshine and gelato — sometimes one kid decides the trip is personally offensive, and suddenly everyone is miserable. That’s when I pull out the love-and-logic approach: give them ownership of their attitude. I’ll calmly say something like, “You get to choose your attitude — either way, we’re going on the trip.” Or sometimes: “You can pout, or you can play — either way, we’re moving forward.” Other times it’s: “You get to feel grumpy, or you get to have fun — your choice.” And occasionally: “You pick your attitude, and the trip goes on with or without it.”

These little one-liners are short, firm, and funny — they acknowledge the grumpy feelings without starting a power struggle. Magically, the drama diffuses: the kid either joins in with a tiny win or takes a short pause, and the rest of the family can enjoy the vacation without a meltdown in aisle three of the souvenir shop.

What Actually Makes a Family Vacation Successful?

It’s not the country.
It’s not the scenery.
It’s not the photos.

It’s:

• Clear expectations
• Thoughtful pacing
• Simple systems
• Willingness to be flexible
• Shared responsibility
• Margin to rest

For us, good planning — and tools that support that planning — are what make big trips doable.

Family vacations don’t need to be extravagant to be meaningful.

They just need to be intentional.

And structured enough that when you finally zip the bags and close the car door, you feel steady… not unraveled.

1-Week Packing List

Click here for my Printable Packing PDFs

(Sized intentionally for structured roller bags)

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For Adults

Clothing (Fits neatly into compartments)

• 4 everyday tops
• 2 versatile bottoms (jeans, shorts, trousers, or skirts)
• 1 casual layer (cardigan, sweatshirt, or light jacket)
• 1 nicer outfit (dress or collared shirt option)
• 1 sleep set
• 7 underwear
• 5–6 socks (depending on the weather)
• 1 pair walking shoes
• 1 secondary shoe (sandals or flats)
• Swimsuit (if needed)

Optional (depending on destination):

• Lightweight scarf
• Compact rain shell

Tip:
Roll outfits together to reduce decision fatigue on the trip.

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For Kids

Kids can pack slightly fewer items than you think.

Clothing

• 4–5 tops
• 3 bottoms
• 1 sweatshirt or layer
• 1 “nice” outfit (church, dinner, event)
• 1–2 pajamas
• 7 underwear
• 5–6 socks (depending on the weather)
• 1 pair sturdy shoes
• 1 secondary shoe (crocs/sandals)
• Swimsuit (if needed)

If laundry is available midweek, you could reduce even more. We’ve been using these lightweight laundry sheets on our last few trips and love them!

Because your Walker Family Roller Bags are compartmented and consistent, kids can visually see:

• Shoes go here
• Underthings go here
• Folded clothing goes here
• Zipper pocket = books or small treasures

That predictability keeps packing fast and prevents the “what if” spiral.

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Shared Family Toiletry Bag

Instead of everyone packing their own:

• Toothbrushes
• Travel toothpaste
• Hairbrush/comb
• Minimal makeup
• Small shampoo/conditioner
• Deodorant
• Basic medication
• Nail clippers
• Small sunscreen (I like throwing my homemade tallow sunscreen in the bag)

One bag. One system. Less clutter.

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Airplane or Car Backpack (One Per Person)

This is where trips either feel calm… or chaotic.

Keep it light but intentional.

For Kids

• Water bottle (empty for airport security)
• One small snack pouch
• Favorite blankie or stuffy
• Headphones
• One book
• One small activity (coloring book, journal, card deck)
• Lightweight sweatshirt
• Tiny zipper pouch for treasures
• Travel pillow (if needed)

No giant toy collections.
No 14 activities.
Just enough.

I like to leave plenty of room in these or things brought back home.

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For Adults

• Wallet + travel documents
• Phone + charger
• Lip balm
• Small snack
• Refillable water bottle
• One book or Kindle
• Lightweight scarf (doubles as blanket)
• Minimal toiletry pouch (toothbrush, deodorant if long flight)
• Any necessary medication

Optional:

• Compression socks for long flights
• Eye mask

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One Shared “Mom Bag” (Optional but Helpful)

If driving or flying internationally:

• Wet wipes
• Extra snack stash
• Mini first aid kit
• A few empty Ziplocs
• Hand sanitizer
• One extra kid shirt (insurance piece)

Our Favorite Screen-Free Things to Entertain Us:

I keep a Deck of Cards in my bag at all times. ALL times.

Sticker by Number and Color by Number books

This fun, hand-held game.

These cameras.

Spot It

Travel Magna-Tiles

The kids’ pocket kites. They could walk all the way down the beach and we could still see where they were because of these kites!

The one thing I won’t leave without. The most versatile thing I’ll always carry:

Our Sandcloud Towels.

I once met a woman while we were on our way to Mexico when I was in college.

She had this beautiful wrap around her. So I asked her about it. She said, she never leaves home without her sandcloud towel.

Since it was wintertime, she’d left her winter coat in their car and used this towel to act like a warm wrap. She said, “Then I’ll use it on the airplane as a blanket or pillow.” “Then I’ll use it to cover up my swimsuit while I walk down to the beach.” “Then I’ll use it to sit on at the beach- you see it repels sand.”

We now have them in several different sizes; each kid has their own. They get folded flat and placed in the front pockets of our Walker Bags, for easy access. I tell you what, they’ve always been multifunctional enough to make our packing lists, but I don’t know what we would have done in the Chicago airport without all our Sandcloud Towels! Bringing them to the very top of the packing list.

Closing Thoughts

It’s important to remember that life still happens during vacation: siblings will fight, someone will somehow become a picky eater the moment the plane touches down, and lost sunglasses are almost a guarantee. Even on the most meticulously planned vacations, life happens (example A: sleeping in the O’Hare airport). Take a breath, look at the company you’re in, and know that with the right planning all of the new treasured experiences are going to be much more memorable than the stress.

Pin for your next Family Trip!

Keep up with our travels!

• What Traveling to Germany Taught Us About Farming, Culture, and Seeing the World Differently
• Luxembourg and Beyond | Citizenship + Travel Tips
• Tuscany in Stillness | Intentional Living, Warm Tables and the Art of Being Still