How to Plan a Sane Family Vacation

Especially if you have small children, planning a vacation may seem like a lot of work. Here, we simplify planning to make your vacation happy and actually happen!
family vacation
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A family vacation, especially with small children can seem like it’s more hassle than it’s worth.  If you have multiple children under 5, you are probably thinking right now it’s a miracle just that you get out the door in the morning!  I feel ya.  I am here to tell you that yes! you can take a family vacation AND keep your sanity.  How do I know? Well, my 6yr old has been on over 50 flights at the time of this posting and my twins started traveling via plane at 6 months old taking 4 flights a year.  Here’s a pic of me alone with all 3 in the airport during my breastfeeding days in 2021… 


I know what you are thinking, “This chick be cray!” I can say that traveling so much with my 1st child prepared me for traveling with 3 because I already knew what worked, what didn’t and what gear I needed to make my life easier. As your kids grow, there is less to prepare for, less gear needed, just more personalities to work with.  I’ll be focusing this post for both little kids and big kids alike. 72% of Americans do not use their vacation time, so let’s change that. 

I’d like to impart my wisdom to you and I’m including a FREE planner that you can download above or below.


Trip vs. Vacation

If you have children under 5, having a vacation is hard!  It can feel more like a trip, meaning you are just parenting in a different place.  Even without help from grandparents or family members, it is possible to still have a vacation, it’s just not going to look like the beach vacation of the past.  You know, the one where you were lying on the beach, bikini strings undone, sipping your mai tai, listening to the sound of the waves.  Let’s take a moment to grieve that life once lived…



Ok, snap back to reality! Or wait? Can this still be your reality (just with a timer for when the babysitter needs to go home)? Yes, it can!  There are a few, and I do mean a few different vacations (notice I didn’t use the word “trip”) where you can relax AND your kids can be taken care of.  

Here they are:

Beaches Resort: This Caribbean resort is not cheap, but it has everything and is all-inclusive.  Their kids’ clubs cater from 0-18yrs with certified nannies and teachers that follow curriculum-based learning activities.  Special needs child? No problem, they are certified to work with special needs. If you want to go out to dinner outside of camp hours? No problem!  You can set up private certified nannies in your room.  Plus there are activities centered around the whole family. 

Disney Cruise Line: I have been on 3 Disney cruises and been to Disney World many times, the cruise is hands down the best vacation considering theme park vs. cruise.  There is something for everyone. A daycare for babies, a kids club for kids, a tween club, teen club, and even an 18-20 club!  A camp counselor would come around at dinner and ask which kids wanted to go to the club and my daughter would be gone!  The clubs feed them and have their own activities that go all day long.  On Disney’s Island, Castaway Cay there is also a kid’s club, so if you want to eat lobster and get a massage at the adults-only beach, it’s possible!  I would use the nursery/kids club primarly during nap time and then go to the adults-only section of the ship where there is a pool, spa, bars, and coffee shop. This is again pricey, but worth it considering childcare, food and activities are inclusive. So what if you are taking a city trip and want a date night or some time to chill or do some adulting? With a click of a button, you can have a sitter come right to your hotel or AirBnB.  I have used this multiple times without a problem.  Feel too nervous? I did initially too, so I purchased a Nest Camera off Amazon prime same day and easily hooked it up to my phone using the wifi facing my daughter’s crib just to check in.  

Here’s the one I used:



Planning a trip can be fun. With babies, kids, or elderly travelers it’s important to understand the routine.  Do babies take a nap? Do the elderly relatives need time to rest as well?  Rather than basing your activity list around the main attractions, I recommend focusing on routine first.  For example, if you have kids under 5, they will probably be able to do 1 activity in the morning, eat lunch, nap, and have another activity in the afternoon that leads into dinner and the bedtime routine.  

Please don’t over schedule your vacation.  Instead, plan an activity you really want to do with 2 backups.  For example, on a recent trip to Disney World, I originally planned Magic Kingdom (Plan A), but if it rained we would move to the Crayola Factory (Plan B), and if the kids were cranky we would hang out by the pool and DoorDash food (Plan C).  If Plan A works, then you can move Plans B & C to another day with backups.  If you have older kids, you can assign them to research the plans and backups and let them be your tour guide the day of the activity so they can feel included in the planning.

It’s important to make sure everyone is on the same page.  Discuss the daily itineraries with the travel party before the trip and discuss the day in the morning and the next day at night so everyone is on the same page. For tracking reservations and tickets, you can use your digital calendar of choice or I recommend using Tripit


The Gear

Ok, let’s shift gears… 


Sorry, I had to!  

Airplane Travel:

Traveling with children and all of their stuff can seem impossible.  In this section, I’m going to focus specifically on traveling via plane because via car is somewhat easier, however you can totally use some of this stuff in the car also. In the picture above where I was by myself, I was able to pack 2 babies, 1 child, and myself in 1 large suitcase.  I checked that suitcase as soon as I got to the airport, which lightened my load leaving me with a diaper bag and breast pump bag I placed in the bottom of the stroller, and my car seat bases and baby carriers that I wore in this backpack: I recommend this specific double one so that you have extra room for baby blankets or other things. 

On the plane, you want to be as efficient as possible. You have limited space and also limited hands if you are holding an infant. If you are holding an infant, it is best for them to be in a carrier so you have hands free for snacks or to read your kindle while baby naps. I recommend this breathable one that easily goes on via velcro and snaps as opposed to the baby wraps that take more time and patience:

Now that your hands are free, snacks are a must and we all know that babies and toddlers need a variety and eat a ton of snacks. No snacks and a meltdown will surely lead your neighbors to order vodka tonics on your 7am flight. I have 2 of these containers that hook onto my stroller and diaper bag so I am snack ready at all times and don’t have to dig into any bags:

Next, you’ll probably need some in-flight entertainment, especially for longer flights.  For kids, I recommend the Amazon Fire Tablet. It is cheaper and a bit smaller than an iPad and includes a FREE year of Amazon Kids. And please don’t be one of “those people” who doesn’t buy the headphones. No one wants to hear the “blip blips” of your kid’s games.

For grownups I recommend the Amazon Oasis, particularly if you have little ones because it is waterproof and we all know which kids comes accidents. It can hold thousands of books and audio files saving space in your bag and if you have your kid(s) occupied with their tablet and snacks, you may just be able to read that juicy summer novel.

These are the main items for the flight.  I also do not recommend bringing small toys, larger ones are easier to find if they fall on the floor. Play-doh and window clings are fun, coloring packs, activity pads, etc.

baby gear
Destination Travel:

Now let’s switch gears to post-airplane travel.  You wait for your stroller and perhaps you are breastfeeding and need some place to do that. With my daughter, I did this everywhere and really wanted some privacy.  With the twins, I discovered most major airports now have Mamavas, which are private breastfeeding pods.   Even if you aren’t breastfeeding and just want a quiet space for your overstimulated child to eat, you can use these for free. This is what they look like…


After you retrieve your luggage, you are probably either heading to rental car or car service.  I have never traveled with carseats beyond the infant ones in the pic above.  Once my kids outgrew the infant seats, I rented carseats directly from the car rental place.  For the price to me, it was always worth it rather than lugging another thing around.  If you only have one infant and travel a lot it is probably worth it to get a Doona. I have heard great reviews on this carseat that turns into a stroller in one motion.  So cool!

To end this section, I going to focus on a couple of highly recommended infant items as older kids typically have their own preferences for backpacks and can sleep in beds.  Whether you are at a hotel or Airbnb, it is easy to use Amazon Prime to ship items you can’t easily access such as diapers, wipes, and baby food.  I always place a prime order the day before I leave and it’s usually ready when I get there at bell services or the Airbnb’s doorstep. If you are traveling and want to try Amazon Prime for free for 30 days click here! 

The last 2 items I recommend infant specific and they are the Boon Bottle Cleaning Travel Set.  This thing is small, fits in a diaper bag, and has been a staple not just for traveling, but also for everyday outings:

Lastly, it is safe to assume that not all hotels and Airbnbs have a place for your baby to sleep.  With my daughter, I have been in situations where there were no more pack n plays available and I wished I had a place to put my baby outside. When the twins were born, my wish came true and I found exactly what I needed!  This travel bassinet can be checked at the gate and can fit in that double backpack I mentioned earlier.  

This gear I have recommended for your next family vacation are my essentials.  When you find yourself stuck with something big and bulky, see what else is on the market as there is surely some way to make traveling easier so you can enjoy your family vacation. 

Enjoy Your Trip

Don’t be afraid to travel with your family.  Include your older kids in the planning, follow routines, and have the right gear for your infants.  Have low or no expectations for whatever happens.  The more people involved, the more becomes out of your control as personalities take center stage. Instead, find the joys in the little moments, take some pics (even if someone is having a tantrum), and enjoy your time together.

family vacation 1

Happy Planning! Hope your next vacation is a blast!😘

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