How to Plan a Relaxing Family Vacation (Because You Deserve a Trip You Don’t Need to Recover From)

When we booked our trip to New Orleans, we made a quiet promise to ourselves: this one was for rest.

Not to pack the itinerary.

Not to see everything.

Not to come home more tired than we left.

Just to be—together, slow, and present.

After a whirlwind season of work and travel, I knew I needed a reset. And maybe more than that, I wanted Clark to have a few days where the only thing on the agenda was fresh air, good food, and snapping photos of anything that caught his eye.

So we slowed down.We wandered cobblestone streets with no plan. We took long walks, sat by the water, and said yes to things like beignets and unplanned coffee stops.It reminded me just how good travel can feel—when it’s done with intention.

Over the years—traveling with kids, squeezing in photography sessions, and discovering some of my favorite stays for families—I’ve learned that stress-free travel isn’t about how organized your packing cubes are. It’s about how you want to feel.

In this blog post I’m sharing a few things that I now always consider when planning a trip that I want to feel like a true vacation. You can use these too to avoid feeling like you need a vacation from your vacation!

How To Plan a Truly Relaxing Family Vacation (That Actually Feels Like a Break)

🌿 1. Lead with feeling

Before I book anything, I pause and ask:

How do I want this trip to feel?Do I need stillness? Laughter? Connection? Or maybe just some sunshine and a break from doing all the things.

That answer becomes the guide for the ENTIRE trip!

For example, do I want to stay in a cozy cabin tucked in the trees? Or head somewhere warm where my kids can run free while I drink my coffee in peace? (Spoiler: sometimes both are true.)

Ask yourself this before any vacation you’re planning so that you have a north star to follow when making your plans. 

👉 If you’re craving quiet and connection, I wrote about our stay at the Kitzof Inn—a place that’s perfect for large family gatherings, or simply spreading out and taking a breath.

🌸 2. Let go of the “perfect itinerary”

I used to think I needed to fill every hour to make the trip worth it.

But honestly, some of our favorite memories came from the unscheduled moments—throwing a blanket on the grass, finding a local ice cream shop, or reading while the kids played nearby.

Now I aim for 1–2 “anchor” activities a day, and the rest is open. A slow morning walk. A nap if we need it. And always, always time to watch the sunset.

As a parent planning a vacation, I know it’s tempting to think that your kids will only enjoy it if they’re constantly doing things. But more often than not, the overly rigid schedule can lead to meltdowns, tantrums, and overtired kids who really aren’t able to enjoy the activities at all. 

Sometimes less really is more! And we all know that kids typically enjoy the most simple activity, so don’t stress it too much.

👉 I shared some of our favorite ways to enjoy slower seasonal travel in this post about winter adventures, but the mindset applies no matter the season.

🏡 3. Choose the right stay (not just the prettiest one)

Modern and fully equipped kitchen at the Pocono Bear Den, featuring sleek stainless steel appliances, granite countertops, and stylish open shelving.

Look I get it! Having an “Instagrammable” destination always sounds like a good idea… until you arrive and you realize that it’s not very functional. For a family vacay, that is NOT the vibe!

Give me an Airbnb with a full kitchen, coffee bar, a stack of board games, and a big cozy couch over a fancy hotel any day.

When a space feels lived-in and loved, I can actually unwind. Bonus points if there’s a fire pit or space for the kids to roam.

Here’s what I encourage you to look for when searching for a family-friendly Airbnb!

👉 I share real-life stays often over on The Wandering Tourists, like a girls weekend in Pheonix with a splash of Sedona , or our cozy escape to Poconos Bear Den—a home we poured so much heart into creating for families like ours.

🎒 4. Pack light, but bring the things that ground you

Do I still overpack? Occasionally. But I’ve learned I’m happier when I have less stuff and more space to breathe.

My must-haves: cozy layers, a book or two, and something small from home—a mini sound machine, or a playlist.

👉 Speaking of easy packing, I put together a guide to 10 go-to clothing items for family travel, with pieces that mix, match, and work wherever your journey takes you.

📵 5. Create mini boundaries for rest

Even if it’s just turning off notifications or setting a phone-free hour during dinner, those tiny moments of disconnect make space for connection.

We’ve started doing photo scavenger hunts when we travel—a way to see things with fresh eyes and get creative together. It’s one of Clark’s favorite things. (And as someone who documents travel for a living, it helps me stay present and playful.)

✨ 6. Embrace imperfection (really)

Not every trip is smooth. But the beautiful thing is: we don’t need perfection to feel peace.

We need to give ourselves permission to rest. To not “do it all.”

To laugh when things go sideways and remember why we came in the first place: to connect, to breathe, to be.

So next time you plan a trip, I hope you give yourself permission to make it easier. Lighter. More you.

Whether you’re headed to the mountains, the coast, or just down the road, may your next escape feel like the deep breath you’ve been craving.

Want more travel tips, slow moments, and cozy stay ideas?

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P.S. If you’re planning a multi-family vacation and you’re looking for ways to make it smooth sailing as possible, this blog post is for you!