How to Plan for Successful Family Vacations with Toddlers

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My husband and I are expert-level travelers. Today I’m going to share with you all of my secrets for how I plan my trip on family vacations with toddlers.

5 Brilliant Tricks I Use to Plan My Trip on Family Vacations with ToddlersLike I said, our family looOoOooves to travel! In fact, my kids have been on more flights in their short lives than many adults. 

We carve out time for travel at least once every few months.  These range from weekend camping trips to multiple-week-long international vacations. And I’m here to help you achieve traveling success with your children.

The biggest secret to successful family vacations with toddlers is in how I plan my trip in the weeks leading up to travel. This is what I’ll be handling today.

This article is jammed packed with info, best to pin it now so you can reference it later. I’ve also got a handy travel checklist (with planning points and a printable packing list!) you have download for free.

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If you’re still deciding your method of travel – check out: Train, Planes, and Automobiles – Booking Travel with Kids. Or maybe you’re looking for some Packing Tips and Tricks for Family Vacations. But if you’ve already got your planning taken care of, I’ve got some cool ideas for how How to Make Your Vacation with Kids FUN and EASY

Disclaimer: This page contains affiliate links.  See our disclosure policy for more details.

Woman Travel

Here are some other things you should be doing as you get closer to your vacation:

1| Figure Out Sleeping Arrangements

After I’ve booked my travel method and the hotel, my next step when I plan my trip is to figure out where everyone will sleep.

If you’re lucky and have kids old enough to already sleep in their own bed, then you can skip this step.  For all others with infants, toddlers, and preschoolers – read on.

A lot of figuring out sleeping arrangements depends on where you are staying.  If you’ve booked hotels, see what options they have for children sleeping.  If you are staying with family or in an Airbnb then you’ll have to contact them to see what’s available. 

Baby Travel Sleep Options

Many hotels will offer complimentary pack n’ plays and sometimes even a bassinet. 

Be warned, these pack n’ plays are well-used and the “pad” on the bottom is often worn and extremely hard.  For this reason I highly recommend bringing a mattress pad designed for a pack n’ play to make sleeping more comfortable, like this one:

These mattress pads are extremely compact and ideal for travel.  They instantly transform a hard, cold pack n’ play into a warm and comfy bed. 

I DO NOT recommend checking a pack n’ play on an airplane (for one, it would cost more than buying one outright at your destination and second, it would be handled extremely rough).

If you are flying and require a pack n’ play (or other baby equipment), consider renting one from a site like BabyQuip.

Just be sure to check what you need to provide.  It’s a good idea to still bring along a mattress pad like I mentioned above, but you may also need to provide your own pack n’ play sheets.

Another option is buying an inexpensive pack n’ play like this one and having it shipped directly to your destination/hotel/rental home.  After you’re done with it you can donate it to a local women’s shelter or even to the hotel.   

Finally, one last unconventional baby travel sleep options I have for very young infants (still swaddled, not yet rolling over) is to use a changing pad.

That’s what I used when we went camping when my youngest was 3 months old (I know I know, we’re crazy but we love it). 

It worked WAY better than I could have expected! 

It was familiar to her and she knew the smell.  It’s firm so I felt confident about it as a sleeping surface.  And it took up hardly any space in the car!        

However, I should add this is obviously not designed for overnight sleep and is not an approved sleeping surface by the AAP.  If you have questions or concerns, please discuss it with your pediatrician.

Toddler Sleeping Arrangements on Vacation

For younger toddlers, a pack ‘n play is always a solid idea.  Many hotels (and even some Airbnbs) offer them so they are easy to find. 

Just be sure to mention you need one ahead of time, as they have a limited number available.  And be sure to bring along a mattress pad (see above for more info this and renting/buying an inexpensive pack n’ play for travel).

For older children who have outgrown the pack n’ play, I have some other excellent toddler sleep arrangement vacation options.

In my opinion, the best toddler travel bed is this inflatable toddler air mattress.  It’s child-sized so it doesn’t take up a huge amount of room (or take forever to inflate). 

The removable center mattress fits a standard crib sheet.  The rim around the center area prevents them from rolling out.  I also find it the perfect height to prevent them from getting out unnecessarily as well.

Another thing we use all the time for travel is this bumper. It easily fits under the sheets in a regular bed to prevent the child from rolling out.


It’s great because it rolls up very tightly so it doesn’t take up much room when packed.  You can easily and instantly convert any bed into the world’s best toddler travel bed and not have to worry about them falling out in the middle of the night. 

Related Post |  Surviving a Road Trip with Toddlers
Related Post |  Essential Packing Tips for Family Vacations

2| Get Psyched Up for Family Vacations with Toddlers

When I play my trip, MONTHS before the family vacation with toddlers we always tell our kids what we’re planning to get them excited. 

We try to pump them up about ALL aspects – from the method of transportation to packing and finally the destination.

They talk about how they can pack some of their toys (usually one big item and a few smaller ones).  We discuss countless times which ones they’re going to bring (and it changes at least daily with all the excitement).

We buy books about how we’re going to travel.  One of our favorites is Planes Go (followed closely by its brother book Trains Go). 

Then we also talk a lot about the exciting things to see, do, and try in the travel destination.  For example, we’re planning a trip to Scotland this Spring so we’ve been talking a lot about … and reading this book about a cute little Loch Ness monster that grows up as a tadpole:

Good Night Nevada is part of the adorable Good Night Our World series that we LOVE because it goes over many cities in the world.  We used to Good Night Nevada to talk about an upcoming trip to Las Vegas. 

3| Plan My Trip with Activities and Restaurants

You don’t have to plan out every day to the minute with a full vacation itinerary (in fact, I recommend specifically NOT doing that), but you should do some research on things you want to do during family vacations with toddlers.

Are you visiting New Orleans?  Well the maybe on your to-do list is walking around the French Quarter, taking a class at the New Orleans School of Cooking, and catching a Jazz show.  Other things you’re thinking about might include getting a drink on Bourbon street, eating beignets at Café Du Monde, and visiting the aquarium.

After you’ve written down a list of activities you’re interested in, start to prioritize them.  What are the things you’ll be absolutely devastated if you miss?  For those activities, look up the times/availability and book tickets in advance. 

NEVER book more than two “essential” activities in the same day.  You want to keep flexible in case your kids need some chill time. 

For the other possible activities, keep that list handy for your trip and use it to fill in the schedule holes.

As stated above, when I plan my trip I certainly do not fill each minute of the day.  You have to be flexible when you’re traveling with kids.  Stay busy and entertained, but be flexible. 

As for dining, I usually start a google map and “save” restaurants that I’m interested in (after reading reviews on Trip Advisor and Yelp).  That way I can pull up the app with my location and find places nearby. 

While I always believe in planning out restaurants, this is particularly important in international locations where you don’t have internet service and can’t always easily yelp “child-friendly lunch restaurant that serves mac n’ cheese”. 

Nothing ruins a day like a hungry toddler… ugh.  So I try to avoid those moments if at all possible. 

4| Start Your Packing List Now

Months before I even open my suitcase I start a list of things I need to pack using the Google Keep App

It may sound crazy, but it’s so much easier when you organically think of items you need to bring (rather than trying to sit down and figure out every item you need).

I’m actually writing this post from a vacation where I unfortunately didn’t follow my own advice.

The item forgotten?

Baby wipes. *Face Palm*

And guess what, I’m on a cruise…. Where they don’t sell baby wipes on board so my best hope is when we stop at our first port in 3 days.

So don’t be like me!

Open the app right now, start a list called “Vacation Packing List”. 

As you think of items, just add them to the list.  You’ll be so much more likely to remember everything this way, I promise. 

Psssstt…. I have a sample packing list and MANY more great planning tips like these on my free Printable Travel Checklist!

5| How I Plan My Trip Transportation

Figuring out how you’re going to get around is important for multiple reasons.

You want things to go smooooth on your family vacations with toddlers – you don’t want to be trying to figure out if you want to take the bus, subway, or taxi when you are dealing with kids in a new environment. 

When I plan my trip I like to minimize transportation concerns by staying at a hotel that is central to the area I’m visiting.  This allows me to walk to most of the destinations I’m interested in.

Sure it’s a little more expensive, but you’ll also save money on taxi fees and a rental car.  And it’s a small price to pay for your sanity.  

If  you can’t stay central in the city, at the very least it’s a good idea to plan to stay close to public transportation (like a subway station or bus stop).  Relying on taxis can be tiring and difficult with car seats.

If your trip is going to require a lot of driving (and therefore lots of car seat demand), one thing to consider is investing in an inexpensive, light car seat for travel.  The Cosco Scenera NEXT is often recommended for this exact purpose.  It’s relatively cheap, compact, and is very lightweight.  Bonus, since it’s convertible it can be used for both rear and forward facing children.

Renting cars can be a GREAT idea if your vacation requires a lot of driving as the car seats can be installed and left there.  Additionally – extra diapers, snacks, the stroller can be easily stored. 


There you have it! Those are some of my important planning tips for how I plan my trip with the family.

Keep yourself busy and follow these tips for planning family vacations with toddlers so the months leading up to your trip will fly by!  Before you know it your vacation will be right around the corner and you’ll have to start packing….

Before you go remember to download my FREE Printable Travel Checklist!

5 Brilliant Tricks I Use to Plan My Trip on Family Vacations with Toddlers

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About Author

Jo

Hi, I’m Jo!

I have two small children, Ry and Lily, only 19 months apart. It’s usually crazy around my house, but thankfully my wonderful husband is around a ton and helps keep the peace.

I also own my own business and work full-time. I’d love to list all these amazing hobbies I have, but honestly I can barely handle keeping the kids entertained, the house clean, and food on the table. Although on days I’m too tired to do housework, I love to pour a glass of wine and watch Supernatural or Murdoch Mysteries on Netflix.

My husband and I like to stay very busy and drag our kids everywhere with us. Weekends often include relaxing at wineries, festivals, exploring Washington D.C. and other short getaway trips.