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10 Ways to Make Summer Travel With Your Littles Easier

July 21, 2025
by:
Anna Stare
for Stareworthy.com

Packing for a toddler can feel like preparing for a six-month expedition...even if you’re only going away for the weekend. But summer travel with your littles doesn’t have to be overwhelming! With the right tips, you can turn long car rides, busy airports, and unfamiliar hotel rooms into opportunities for sweet family memories.

Here are 10 ways to plan smarter, stress less, and focus on making magical moments together!

1. Pick The Right Destination

When thinking of where to take your big trip, try to choose a place that’s family-friendly. Think accommodations with cribs, high chairs, play areas, or nearby parks. Many vacation-friendly areas are home to businesses that offer toys, games, and equipment rentals. Don't have room in your car for the stroller? Book one online ahead of time! Don't feel like fussing with the pack n' play in the airport? Rent one to be delivered right to your home away from home. Another helpful tip here: when possible, choose places that you've visited previously. When we explore a new destination, we feel added pressure to get out and see as much as possible, or else we don't feel like we're making the most out of our trip. If you need a getaway with your family but don't want to feel obligated to do and see everything (all while planning around nap time, feedings, and tantrums...oh my!), try bringing your little one to a place that you already know and love. For even if you've been there and done that, experiencing it for the first time through your child's eyes is its own special kind of magic. Once the kiddos get a little bit older and more independent, bring on the new!

Bonus tip: For added peace of mind, make sure your lodgings have easy access to grocery stores and healthcare if needed.

2. Travel Around Their Sleep Schedule

Whenever possible, time flights or drives during naps. Build in buffer time for meals, diaper changes, and play stops. Less cramming, more calm. Your future self will thank you!

Every parent knows: nap time is sacred. And when you’re traveling, it’s even more important. Plan travel around the windows of time when your child is most likely to rest. For car trips, this might mean leaving right before nap time so they can fall asleep to the hum of the road. For flights, choose departure times that align with natural rest periods. When that’s not possible, create a “sleepy-time kit” for travel days: a favorite blanket, a portable white noise machine, and even a small travel pillow can help mimic the comforts of home. Try to keep pre-nap routines consistent, even if you’re sitting in an airport terminal. A story, a snack, and a few minutes of quiet can cue their brain that it’s time to rest. And remember: kids will pick up on your stress. If you’re calm about delays and changes, they’re more likely to stay calm, too. One seasoned Reddit parent put it best: “We don’t schedule trips for when the kids can handle it, we schedule them for when we can handle the kids.”

3. Streamline Your Packing

There’s an art to packing for littles, and it often involves packing less than you think...while somehow still being prepared for everything. The secret is to focus on multi-purpose items. A muslin blanket can serve as a nursing cover, stroller shade, picnic mat, or emergency burp cloth. A zippered pouch can carry snacks one day and wet swimsuits the next.

Packing cubes are a parent’s best friend! Separate outfits by day or type, so you’re not digging through the whole suitcase for one missing sock. And don’t forget a small “day bag” with essentials like wipes, sunscreen, snacks, and a change of clothes. That way you don’t have to unpack your main luggage every time you need something.

One Reddit traveler swears by the “two outfits and wash” rule for kids: “We bring two days’ worth of clothes and just do a quick sink wash at night. Saves so much space.”

Bring only what you truly need, focusing on multi-use items like muslin blankets (hello, stroller shade, picnic blanket, and nursing cover in one!). Pack comfort items from home like a favorite stuffed animal or bedtime book, and keep snacks, wipes, and a small first-aid kit within reach.

4. Keep Them Busy On-the-Go

A bored toddler is a ticking time bomb, so plan for variety. Bring quiet toys, board books, and activity pads, and rotate them throughout the trip so each one feels fresh. Dollar-store finds or thrifted books work great here— you won’t be heartbroken if they get lost or damaged.

Digital entertainment can be a lifesaver too, just choose wisely. Download short, age-appropriate shows or songs, and keep them for last-resort moments. If you want to avoid screens, audiobooks can be surprisingly effective (toddlers love silly voices and sound effects!).

Another fun idea: wrap small toys in tissue paper like presents. Every hour or so, let your little one “open” something new. It turns travel into a series of fun surprises and helps pass the time!

Quiet toys, board books, and a few downloaded songs or audiobooks can be game-changers. Rotate activities to keep things fresh, novelty is your best friend when the hours stretch on.

5. Accept That Things Won’t Go Perfectly

If there’s one truth about traveling with littles, it’s this: something will go wrong. A nap will be skipped, a snack will be spilled, a meltdown will happen in public. And that’s okay.

The more you can release the idea of a “perfect trip,” the more room you leave for real joy. Focus on one or two activities per day, and let the rest unfold naturally. Maybe you skip the afternoon museum and splash in the hotel pool instead? That could end up being your child’s favorite part of the trip.

One Reddit parent summed it up: “Lower your expectations and slow down— kids will pick up on your energy.” When you treat travel as an adventure rather than a checklist, the memories you make will be sweeter. Sometimes the best memories are made when plans change last minute!

6. Give Them Choices

Toddlers aren’t exactly known for their flexibility, but they are more cooperative when they feel like they have a say. Simple choices like picking between two shirts or deciding whether to visit the park before or after lunch can give them a sense of control.

This works especially well for easing transitions. Heading back to the hotel? Let them choose which path to take or which snack to have when you get there. It turns “We have to go” into “I get to decide,” which makes them more willing participants.

It’s also a way to spark conversation. Ask open-ended questions like, “Which stuffed animal should come on the trip?” or “Do you want to help pack the snack bag?” Their answers might be adorable and you’ll get a peek into what matters most to them.

Toddlers really love feeling included— let them choose between two shirts for the day or pick a toy for the trip. It builds excitement and cooperation, and you may be surprised at how proud they feel being “in charge.”

7. Plan Simple, Kid-Friendly Meals

Nothing derails a travel day faster than a hungry toddler. Before your trip, research restaurants with kid-friendly menus, high chairs, and quick service. Keep a stash of portable snacks like fruit pouches, string cheese, or crackers for those moments when mealtime gets delayed.

If your child is adventurous, involve them in trying a local specialty. Even a single bite can become part of the memory. If they’re pickier eaters, that’s fine too. Sometimes eating a familiar snack in an unfamiliar place is comforting.

One family I know always travels with collapsible silicone bowls and a tiny set of toddler utensils. They can serve breakfast in a hotel room or snacks on a park bench without fuss. Little systems like this can save you a lot of “hangry” moments.

Bonus tip: Research kid-friendly restaurants ahead of time or pack easy snacks for picky eaters. If your little one is adventurous, try a local treat together— instant travel memory!

8. Have a ‘Surprise Stash’

A surprise stash is exactly what it sounds like: a bag of small, new-to-them items you only pull out in moments of need. This could be stickers, coloring books, tiny figurines, or even a new snack.

The key is novelty. A toy they’ve never seen before will hold their attention far longer than a favorite they’ve played with a hundred times. Some parents like to hand these out at specific milestones (after security at the airport, halfway through a road trip, etc.) to create a sense of reward and excitement.

Pack a small bag of new toys, stickers, or coloring supplies to pull out during tough moments. As one Reddit user joked, “Bribery works, just make it adorable.” Sometimes, that adorable bribe is the difference between a peaceful journey and a public meltdown.

9. Build in ‘Breathing Room’

When you’re traveling with littles, the magic often happens in the unplanned moments. Resist the urge to schedule every hour— leave pockets of free time between activities for wandering, playing, or simply relaxing together.

That “extra time” might mean stumbling across a local playground, watching ducks at a park, or enjoying an impromptu ice cream stop. These unplanned experiences not only reduce stress but also give your child time to process and enjoy their surroundings, making the trip feel like an adventure, not a marathon.

10. Document the Moments and Keep the Memories Alive!

It’s tempting to focus only on “big” moments— monuments, rides, special meals, etc. However, it’s often the small details that your family will cherish most. The way your toddler’s hair curls after swimming, the snack you shared on a park bench, the silly game they invented in the hotel hallway.

Take quick snapshots throughout the day, and don’t worry about them being perfect. In fact, the candid ones often end up being the most loved. Keep a small journal or notes app handy to jot down funny quotes or special moments you might otherwise forget!

Later, these notes and photos can be used to create a keepsake, like our Away We Went book that turns the experience into a story your child can revisit over and over.

Your trip doesn’t have to end when you unpack. Away We Went is a professionally written, beautifully designed book that helps your child relive their favorite vacation moments.

This ask-and-answer style story invites your child to recall key details— What did we see? Who did we meet? What was your favorite part?— framing the experience in a way that helps them remember it for years. And unlike a set of photos tucked away in your phone, this book sits proudly on their shelf, ready to be enjoyed at any story time. Create your very own Away We Went today and start preserving your child's travel memories!

Snap photos of silly faces, snack breaks, and bedtime stories in new places. These small details are the ones you’ll want to remember—and they make great conversation starters when you look back on your trip together.

Bonus Tip...

If your little one struggles with transitions, start talking about the trip well in advance. Read travel-themed children’s books, show them photos of where you’re going, and involve them in small decisions to make the adventure feel exciting rather than overwhelming. Even a simple “countdown to our trip” calendar can help build anticipation and make the change feel less sudden.

Final Thoughts

Traveling with babies and toddlers isn’t about perfection, it’s about connection. With thoughtful preparation and a willingness to slow down, you can make this summer’s adventures some of your family’s happiest memories!

And when you’re ready to relive those moments again and again, Away We Went will be there to bring them back to life— smiles, sandy toes, and all!

Anna Stare
Anna Stare is a Charleston-based author and photographer with a passion for storytelling, memory-making, and early childhood development. She founded Stareworthy Custom Children’s Books to help families preserve real-life moments through heartfelt, rhythmic stories using their own photos. Anna writes all of Stareworthy’s books and contributes regularly to the blog, where she shares tips, insights, and inspiration for parents and caregivers of young children.
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