Vacationing with Toddlers? Piece of Cake.
My original concept for this post was to share my very best tips for vacationing with toddlers. After all, I’ve got toddlers… and I’ve travelled with them…. so that makes me qualified to dole out advice, right? Right?
The thing is, I may as well be giving tips for scaling Atlantic salmon or refinishing a picnic table, because truthfully, I’m no expert. I actually avoided family travel for years, rationalizing that any vacation where you bring your kids along is NOT A VACATION at all. And in my suitcase headed down south, the last thing I wanted to pack beside my swimsuit was swim diapers.
That was before last year. As you may recall, I vacationed with my family for the first time aboard the Royal Caribbean Allure of the Seas with my fellow #FisherPriceMoms. And if you remember this post, you’ll also recall that I was FREAKING. OUT.
How will they behave? Will it be difficult being away from home? What should I pack? How can I keep them entertained on the plane? OMG!
Turns out, with a little deep breathing and a lot of preparation, the trip was a success! In fact, we enjoyed family travel so much that we did it all over again the following month at Walt Disney World in Florida. And after our second experience, I started to get really comfortable with it. Maybe not quite “expert” status, but certainly confident enough to share my favourite tips for vacationing with toddlers. It’s just what worked for us – and for those families embarking on their first trip together, I’m hoping my suggestions will work for you too.
(And here’s an official #SQUEE! moment – my family will be returning to Orlando next week as part of a family travel program with Visit Orlando! We’ll be experiencing some of the world-class attractions the city has to offer… Sunshine State, here we come! Stay tuned for about our fabulous trip.)
1. Be Prepared. Like a Boss.
You’ve probably heard this one before, but being prepared is simply the best way to have a successful family vacation. In fact, your only mandate is to anticipate every meltdown, every moment of boredom, every minor accident, and certainly every fight between siblings. If you can do that, everything else is easy-peasy! Sounds overwhelming? It’s not. Just prepare yourself by making a list – directly matching up scenarios and solutions. For example:
Hunger – Goldfish Crackers
Boredom – Dollar Store Books
Rewards for Siblings Not Killing Each Other – Lollipops
Funny Tummy – Probiotics
Boredom – Dollar Store Puzzles
Homesick – Blankie and Favourite Toy
Grumpy – Printed Itinerary with Pictures*
Boredom – More Dollar Store Disposables…
* This is actually my favourite distraction technique. Showing the boys pictures of the places we’ll be going, what we’ll be doing, etc went a long way to get them excited about the trip and keep tantrums at bay. Whenever one or the other was nearing his breaking point, I simply pulled out my colourful brochures and asked him to point at what he was most excited for, and why. Crisis averted!
2. Consider Flying at an Inconvenient Time.
Okay, so nobody wants to fly early in the morning or late at night. With travel time, airport check-in and customs/ security lines, your wake-up call could conceivably be at 4:30am. But do you know what toddlers do when you have them up bright and early in the wee hours of morning? They sleep on the plane. Preferably, for most of the flight. This allows you to bypass at least 23 distraction techniques altogether! Now I know this goes against conventional wisdom to keep sleep patterns the same, but let me tell you – with my boys snoozing away on both departing and return flights, I wasn’t too worried about their sleep patterns. In fact, I finally got some “me time” while watching the in-flight movie (I passed on Magic Mike – too embarrassed at what the people behind me would think – but The Descendants was a very good second choice). Of course, if your child is the type to be wide awake after he/she rises in the morning, this technique won’t work for you. Sorry :(
3. Book a Well-Toddler Checkup.

The thing about toddlers is that they don’t always tell you when they’re not feeling well. Especially in cold/flu season, consider having them checked by your family doctor a day or two before you depart, especially if they’ve recently been ill or are currently under the weather. From previous experience, Reid had a cough and cold before our Royal Caribbean cruise. I took him to the doctor for his cough – only to find out he had a raging ear infection in both ears. Had we flown with his ears in such bad shape, we would have risked severe damage to his ear drums. The following month, just before we left for Disney World, he again had a runny nose and fever. I took him in to err on the side of caution – wham-o! Another double ear infection – bad enough to require another round of the pink stuff. (I asked Reid umpteen times if his ears hurt, and he said no! Never trust a two-year-old.) Starting the antibiotics even a day before you leave is enough to take the edge off the infection and allow for safe air travel. So if your toddlers are ill, don’t play doctor – take them to one.
(Of course, if your doctor looks like George Clooney, you may want to book a physical for yourself too. You know, strictly as a precaution.)
4. It’s Not About What They’ll Remember.
Here’s an excerpt from my post “The Most Magical Place on Earth…”
“Before leaving for Disney World, I often questioned if the boys were too young to fully appreciate the experience. “Reid’s too young to remember any of it”, I complained. However, once we arrived at Magic Kingdom, I realized that all of my pre-conceived notions were dead wrong. Because it’s not about what they’ll remember; it’s about what they are experiencing in the moment. Seeing the joy on Reid’s face as he travelled along The Many Adventures of Winnie the Pooh made my eyes glisten with happiness. Hearing Ryder scream “I want to do that again!” after racing through the Tomorrowland Speedway confirmed that Disney World is for all ages, from 2 to 102.”
No matter how old your children are – or how old you are – it’s always the perfect time for a family vacation. If you’re looking at your toddlers thinking, “I’ll wait until they get older so they can remember the trip”, here’s some sage advice: sometimes, tomorrow never comes. Live in the moment; love each minute you have with your children. If you’ve been wanting to get away, do it today. Maybe the kids won’t remember it – but hey, I don’t remember much about a trip I took to Cancun when I was 24. I’m pretty sure I still had an awesome time.
5. The Resources Are Out There. Use Them.

Want to take some of the guesswork out of planning a family vacation? Check out the Thomas Cook Kids First program. Kids First is unique Kid Reviewed, Parent Approved program that offers video reviews of top destinations from a kid’s perspective, expert advice from knowledgeable Kids First travel specialists and exclusive partner offers.
So if you’re wondering if a resort is truly “Child Friendly”, well, who better to hear it from than a child! Browse through videos, reviews and perks that will allow you to book your family getaway with confidence. As an added incentive, when you book your vacation with Thomas Cook Kids First, you’ll receive up to $500 in BONUS value -
• $50 Prepaid VISA Gift Card
• $25 Indigo Gift Card
• $25 Shoppers Drug Mart Gift Card
• FREE Seat Selection
• FREE Airport Lounge Pass
• FREE Kids First Activity Book
• 1-year Subscription to Today’s Parent Magazine
• Park ‘n Fly Savings
Okay, not sure about you, but I could certainly use those extras! Prepaid Visa for boredom cures, books and magazines from Indigo, maybe some travel essentials like sunscreen and travel-sized beauty products from Shoppers. So well thought-out!
Hope these tips are helpful! Now tell me… if you could vacation anywhere right now, where would it be?




















Aruba, please! Beautiful beaches…
Thanks.
Come walk with me along the sea, Along the road that no cars travel. Just the birds and me
And listen to the beat of the sea in Turks and Caicos
Great advice Lena, I”ll be sure to pass this off to my wife
Bahamas :)
I would love to be in Ochos Rios, Jamaica right about now! What is the temperature outside? “Feels like” -25!
Caribbean sounds great!
I would love to take my family to Jamaica, specifically Montego Bay or Runaway Bay.
I’ve always wanted to go to Turks and Caicos!!
I’ve never been to Aruba and would love to go there. With today’s weather,I wish I could go today!
Never been to Turks and Caicos – would love to go there!
Perhaps anywhere but here Brrrrrr!
On this cold winter’s day I would like to be on the Riviera Maya of course!
Aruba!
Turks & Cacios
I would love to go with my family to Riviera Maya.
Aruba or Turks & caicos. Any place warm would do though.
Orlando has so much for a family to do.
I would love to travel to St. Lucia
thanks
Really? It wouldn’t matter to us if we were in Aurba, Jamaica or Turks and Caicos – anywhere with sunshine and water would do us fine.
Your post couldn’t be better timed as we are vacationing soon and you offered some great tips
St Lucia
i would love to visit turks and caicos with my family! thank you! (and love all your suggestions about travelling together with kids!)
I’d love to go to Aruba!
The Blau Marina Varadero in Cuba looks amazing! Those beaches!
I enjoyed reading this article. I was not sure how to entertain boys but now I see. I really liked you ideas and suggestions. Enjoyable article, Lena
Jamaica or Turks and Caicos.
I’d like to go to Aruba.
I’d love to go anywhere, no one in my family has ever gone anywhere warm. Mexico might be nice.
we would like to go to cuba
I’d love to go to St. Lucia
Jamaica would be lovely
St. Lucia
Definitely Turks and Caicos!!
I would like to go to the Caribbean with my family and enjoy the sun and the beach.
silverneon2000 at yahoo dot com
that St Lucia sure looks inviting and warm
Jamaica
Aruba.. we love it there!
I love the advice that you have for travelling with children. I would love to go to Mexico with my Mum and daughter, Sara. Sara has been a few times…actually everyone in my family has been but my Mum and I haven’t and she deserves a break :)
St Lucia looks amazing!
Riviera Maya.or Cuba
I’d like to take the boys to Disney World.
I would really like to go to Turks and Caicos.
I would love to go to St. Lucia
St. Lucia – Coconut Bay
Turks and Caicos would be great to visit with my family!
Anywhere right now, but let’s start with Cuba!!
St. Lucia sounds divine!
Ochos Rios, Jamaica
I just loved Hawaii
I would love to go to St. Lucia
I would love to visit Aruba :)
Would like to go to Jamaica
cuba!
Cuba – Husa Cayo Santa Maria Beach sounds fantastic.
I’ve always wanted to go to Aruba!
I would love to take the family to St Lucia.
Anywear warm without snow!!
Jamaica
St. Lucia!!
Disney!!
Anywhere in the Caribbean.
I would love to go to St. Lucia with my family or any of those places really!!! A family vacation would be wonderful right now.
Riviera Maya
Turks and Caicos
Jamaica
Riviera Maya
I would love to go to the Beaches Negril Resort in Jamaica.
I’d love to go to Beaches Turks & Caicos.
Hawaii – near Waikiki Beach
I’d love to go to coconut bay in st. lucia!
i would like to go on one of the disney cruises.
St Lucia
I want to go to St. Lucia!
I would love to go toTurks & Cacios
Aruba!
anywhere. I have never even been outside of canada in my life, and winter is getting boring lol
Montego Bay (Jamaica!!)
St. LUCIA! :)
I’d love to go to mexico or st.lucia. Both would be beyond amazing!!
I’d love to go to Cuba. I’ve heard a lot of friends have great vacations there. But really I’d be happy to go anywhere.
Id love to go to Aruba!
I think Turks and Caicos would be great Never been and on bucket list
Aruba
aruba!
vacationing with toddlers was not my idea of a vacation! I brought my daughter on our honeymoon to Jamaica. To make a long story short…it was not a honeymoon and i could not get back home to Toronto soon enough!!
So here we are contemplating another vacation this Spring and we have been debating whether to bring the little one. Everyone says leave her at home…truth be told…I would love to have a childless vacation ANYWHERE…..but I couldn’t. It just would not be a vacation as a piece of me would be missing. So thank you for the extra tips Lena…I will keep them in mind as we prepare for our next family vacation.
Anywhere hot with fun activities for kids…as a mom you take what you can get!
I’ve made two tried with my little girl and both has been so stressful! The first was a 3.5 hour one way road trip to see my in-laws on an acreage. Turns out my little one has super sensitive skin and broke out in an all body rash! Not fun. The second trip was to Walt Disney World when she was 13 months old. Our first mistake was taking the red eye flight – we didn’t get to sleep. So the first day there was such a blur. My daughter slept through all of the fun attractions & woke up just as we were taking the Disney bus back to our resort hotel. Sigh. Maybe next time we’ll try a kid-friendlier place.
Waikiki Beach
Florida
Cuba would be great
Fiji would be nice.
cuba
beaches jamaica
Just came back from Cuba, but I would love to see Jamaica!
Bermuda has always been on my must see list.
Mexico
I want to visit all of the Caribbean Islands.
I really want to experience Disney with my kids, but Hawaii would be nice and relaxing..
I would like to go to Jamaica
I just love Curacao
Somewhere in the Caribbean would be nice….
We left our 4yo + 18mo at home last March and took the 2mo to Waikiki. After seeing our pics, our 4yo asks ALL.THE.TIME when she gets to go see the turtles. Traveling with a 2mo is great, by the way: no toys, extra snacks, in room nap times(unless you want to). Since she was bf’d, all we needed were diapers. And we had a stroller to lug around all our stuff from the beach to the hotel. Too bad it was the rainiest week in 50 years. :/
I’d love to go to the Caribbean too one day.
St. Lucia would be nice, or Hawaii. Anywhere warm LOL
I would love to see Jamaica this winter
I really want to go to Aruba.
Turks and Caicos, I have heard great reviews and it looks so beautiful
Negril
Jamaica
Jamaica
Antigua
i’d love to holiday in Punta Cana!
Jamaica would be awesome
i would love to go to the bahamas
Would love to go back to Aruba
Mexico pretty please
Curacao is beautiful this time of the year
Aruba to look at the Divi Divi trees
Aruba would be amazing!
Montego Bay in Jamaica would be heavenly
Ireland and Scotland are my hearts desire for travel destinations!
I start to get buggy after 3 hours in the air. So Mexico for me! Its the closest, lol
Dreams Villamagna Nuevo Vallarta looks lovely.
I’ve never taken my kids on a vacation for the same reasons. Would love to take the to Sea World right now, they are really grooving on marine animals.
..oh, and to pick from Thomas Cook’s offerings…We’d love the Grand Palladium, Punta Cana in the DR. Those rays would be nice about now.
Anywhere really!! But Turks & Caicos would have to be top of my anywhere list!
Turks & Caicos is somewhere I need to visit.
I’ve always wanted to go to Turks and Caicos!! Sailing and diving…
Definitely Disney with my little one :)
Been to the US Virgin Islands but would love to return someday.
Aruba has beautiful beaches.
St. Lucia!
greast tips!
Great tips for travelling with young ones. I have yet to go far with my 2 and after reading this I am not so stressed.
Such good ideas! I brought my daughter to Mexico when she was 10 months old. It was fun.