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How to Plan a Round-the-World (RTW) Trip with Kids: A Step-by-Step Guide
- 4 days ago
- 16 min read
Have you ever looked at a map and wondered whether your family could take a few months off to travel the world together?
Before we left Calgary for our own 100-day sabbatical across ten countries, we spent countless evenings wondering exactly that, and whether it was realistic, affordable, or even responsible.
Three months later we had taken a family cooking class in Tokyo, crawled through the Cu Chi Tunnels in Vietnam, explored the ancient temples of Angkor in Cambodia, cruised down the Mekong River through Laos, spotted wild koalas in Australia, and met up with family in Thailand, Bali and New Zealand.
What started as a pipe dream became one of the most rewarding things our family has ever done together, and we came home with thousands of photos, a few genuinely funny disaster stories, and a much better sense of what our family is capable of.
If you're considering a round-the-world (RTW) trip with children, this guide walks through the exact process we used to plan our own 100-day family adventure.
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Table of Contents
Make It a Shared Dream
Looking back, our family sabbatical was years in the making before we actually booked a flight. Like many great ideas, it started as a bit of a pipe dream.
While I was sitting at home during the COVID pandemic, I found myself dreaming about all the places in the world I wanted to show the girls one day. While everyone else seemed to be cancelling trips, I was quietly planning one. Not for the following year, but for some undefined point in the future when the world reopened.
At first, I kept the idea mostly to myself. Instead of discussing it, I researched it. What started as the occasional Google search quickly turned into a bit of an obsession. I spent countless evenings reading family travel blogs, comparing hotels, looking at flight routes and building itineraries of my own.
In my mind, this wasn't a three-month trip. I wanted a full year around the world. I had spreadsheets, budget estimates and destination lists covering multiple continents.
Eventually, I decided it was time to share my grand plan with Susie. The response was probably what most people would have expected. Rather than being excited, she was completely overwhelmed.
To be fair, I don't blame her. I had spent months researching the trip, while Susie was hearing about it for the first time. From her perspective, it was all just a bit too much. The idea wasn't rejected, but it was clear we weren't on the same page.
Over the following year, we talked about it more and more, and the idea gradually started to feel more realistic. Did we really want to be away for a year? What were we hoping to get from the experience? How long would feel exciting rather than overwhelming? What about the kids' school?
Eventually, we came to the conclusion that three months felt right. It was long enough to properly experience different countries and cultures, but short enough that school, work and finances still felt manageable.
It had finally become our dream rather than my dream.
Involve Your Kids in the Planning
One mistake I think many parents make when planning a family trip is treating the children as passengers instead of participants. We tried hard not to do that.
From the early stages of planning, we involved the girls in conversations about where we might go and what we might do. We talked about the animals they wanted to see, foods they were brave enough to try, and the experiences they were most excited about.
Some evenings we'd find ourselves watching YouTube videos of kids eating insects in Thailand, or of people sampling street food in Japan, all in an effort to build excitement for the adventure ahead.
Not every idea made it into the final itinerary, but involving the girls from the beginning gave them a sense of ownership over the adventure long before we left Calgary.
It also gave them plenty of time to process what was happening. We made the decision around 18 months before we set off, so it never felt like a sudden announcement or a surprise. They had time to think about what it would mean for their friendships and school.
By the time departure day finally arrived, they much more excited than they were nervous and couldn't wait to get started.
Decide What Type of Trip You Want
When people hear the phrase "round-the-world trip", they often imagine travelling on a shoestring budget, carrying a backpack and constantly moving from place to place.
While that might be the perfect adventure for some families, it wasn't quite what we were looking for at this stage of our lives.
Early in our planning, we spent a lot of time discussing what type of trip would work best for us and our budget.
Did we want to stay in luxury hotels throughout the journey, or were we comfortable mixing in budget accommodation? Did we want to pre-book all hotels or just wing it like we did when we travelled in our 20's? Were we happy taking overnight buses and sleeper trains, or would we prefer to fly where possible? How much comfort were we willing to sacrifice in exchange for stretching our budget further?
In the end, we settled on a blend of accommodation experiences. Over the course of the trip we used Marriott Bonvoy points to stay in some incredible hotels, but also spent time in local homestays, and even stayed on a rice farm in Laos. We wanted to kids to really benefit from a range of travel experiences.
We'll share exactly how we used points to cover almost half of our 100 nights, plus whether it was actually better value than paying cash, in a dedicated post
The same approach applied to transportation. We took international and domestic flights, travelled by Japan's famous Shinkansen, rode overnight sleeper trains and buses, and spent two memorable days cruising down the Mekong River on the Shompoo slow boat in Laos.
We tried to strike a balance between seeing what we wanted to see and slowing down enough to enjoy it. Having completed several multi-week road trips across Canada, we already knew that our family tends to travel at a fairly quick pace. That works well for us, but it certainly isn't for everyone.
Before you start building an itinerary, spend some time thinking about what pace, comfort level and style of travel suits your family.
Choose Your Destinations Carefully
Choosing where to go was easily one of the most enjoyable parts of planning the trip. Between browsing travel blogs, watching YouTube videos and getting sucked into an endless stream of Instagram reels, it felt like every day we were adding another destination to the list.
The problem, of course, is that for most families there are far more amazing places in the world than anyone can realistically visit in a single trip. It can be really difficult to narrow it down.
What eventually helped us was taking a step back and looking at the trip as a whole rather than as a collection of individual destinations.
Free download: we've made a copy of the itinerary spreadsheet we used available for free, along with a YouTube walkthrough showing exactly how to use it and modify it for your own travels. Grab your copy here.
Weather
Weather was definitely one of the most important factors we considered during the planning process.
There's no point dreaming about a destination for months, only to arrive and discover you've picked the least enjoyable time of year to be there. Japan, for example, is an amazing country to visit, but I'm not sure we would have enjoyed it nearly as much in the heat and humidity of August.
Canada is one of the world's most sought-after travel destinations, but many visitors are surprised to discover (when they arrive) that some of the most popular hikes in the Rockies can still be snow-covered well into the shoulder season.
Even our decision as to which island to visit in Thailand, was largely driven by seasonal weather patterns.
Before falling in love with an itinerary, spend some time researching the climate and seasons in each destination.
Cost of Travel
Of course, cost was another major factor in shaping our itinerary.
One of the benefits of a round-the-world trip is that you can balance expensive destinations with more affordable ones. While countries like Japan, Australia and New Zealand can be relatively costly, destinations such as Vietnam, Cambodia, and Laos offer incredible value for money.
This was one of the reasons we spent two months exploring Southeast Asia. Not only did it offer amazing food, culture and family-friendly experiences, but it also allowed us to stretch our budget much further than we could in places like Europe or North America.
I'll share a full breakdown of what our 100-day trip cost in a separate post, but understanding the relative cost of different countries can make a huge difference to the overall cost of travel.
Food and Culture
One of the things we were most excited about was exposing the girls to different cultures, and food is one of the easiest and most enjoyable ways to do that.
Japan offered everything from sushi and ramen to strange (to us) snacks found in convenience stores. In fact, one of our highlights was taking a family sushi-making class in Tokyo, which gave us a much deeper appreciation for Japanese food and culture. We are still in touch with the lovely family that ran the class.
Later in the trip we had a similar experience in Thailand, where we learned how to prepare authentic Thai food during a cooking class in Koh Lanta.
Some families might prioritise beaches, wildlife or museums. For us, food became an important part of deciding where to go.
Safety
Safety also played a role in our planning. While there are countless amazing destinations around the world, not all of them are suitable at every point in time.
Myanmar is a good example. It was initially on our shortlist, but after researching the situation and reviewing travel advisories, we ultimately decided it wasn't safe for our family to travel there at the time.
For us, the goal wasn't to avoid adventure. It was to choose destinations where we felt comfortable travelling with two young children.
How Long Should You Travel For?
One of the earliest questions you will need to answer is also one of the hardest.
How long should you be away for?
As mentioned above, I initially pushed for a full year of travel, while we eventually settled on 100 days. A year sounded incredibly exciting, but the more we discussed it, the more we realised it wasn't the right fit for our family.
School, work, family commitments and finances all had to be carefully weighed before we could commit to being away for an extended period.
For our family, 100 days felt like the perfect middle ground. It was long enough to immerse ourselves in different countries and cultures, but short enough that it still felt manageable from a practical perspective. We could step away from our normal routines without completely pressing pause on our lives back home.
At the same time, it wasn't so long that we felt disconnected from home. We still had family visits planned throughout the trip and a clear date in mind for returning to Calgary.
The right answer will be different for every family. Some may only have a month available, while others might choose six months or even a full year.
Create a Realistic Budget
At some point every round-the-world travel dream collides with a spreadsheet!
One of the first things we discovered was that there isn't really a single answer to the question, "How much does a trip like this cost?"
The amount of money you spend travelling the world can vary enormously depending on your destinations, accommodation choices, and travel style.
Rather than trying to create the cheapest possible trip, we focused on creating one that represented good value for our family.
There were places where we deliberately saved money, and others where we decided it was worth spending a little more. Using hotel points helped significantly, allowing us to redeem points for almost half of the nights on the trip.
We were also fortunate to spend time with family in Thailand, Bali, and New Zealand. Sharing accommodation costs helped make those destinations more affordable, while also creating some of the most memorable experiences of the entire trip.
The biggest lesson we learned was that budgets need flexibility. No matter how much planning you do, unexpected expenses will appear. Flights get changed. Activities get added. Sometimes you discover experiences that simply feel too good to pass up.
A reminder to check out our free Itinerary Planner Google Sheet. The planner doesn't just help you build your itinerary, it also includes a comprehensive budget tracker that lets you estimate and monitor your costs.
Booking Flights and Accommodation
Before planning this trip, I assumed everyone travelling around the world used some sort of magical round-the-world airline ticket. The reality is a bit more complicated.
We spent a lot of time researching RTW tickets and quickly discovered that while they can offer excellent value for certain itineraries, they also come with restrictions. Fixed routing requirements and reduced flexibility didn't really suit the style of trip we were planning. Instead, we chose to book individual flights.
For our route, this gave us far more freedom. We could choose different airlines, take advantage of regional low-cost carriers, and adjust parts of the itinerary as our plans evolved.
There isn't a right or wrong answer here. Some itineraries work well with RTW tickets. We used one when we travelled the world as twenty-somethings, and it was an amazing way to travel right around the globe.
One of the biggest advantages of booking separate flights was that we could secure them as soon as they became available. This gave us certainty around our travel dates much earlier in the planning process, which in turn allowed us to start booking accommodation well in advance.
Once our flights were locked in, we gradually booked almost all of our hotels, transportation, and major activities before we left home. We found having the majority of our trip organised gave us enormous peace of mind, particularly when travelling with children.
One lesson we learned was to book cancellable reservations whenever possible.
My recommendation would be to price both RTW tickets and individual flights early in your planning process and decide which approach best suits your route and travel style.
Expect the Unexpected
Something unexpected will happen. Not might. Will.
Sometimes it will be challenging: a missed connection, bad weather, a delayed flight, or a child getting sick. Other times it will be positive: an unexpected hotel upgrade, a memorable conversation with a local, or a travel tip from another traveller that leads to an experience you would never have discovered otherwise.
Some of our most memorable experiences happened because our plans changed. We had intended to visit Hoi An, but severe flooding and a typhoon forced us to rethink our itinerary.
Instead, we flew to Malaysia, where our journey got off to a rough start when our flight from Kuala Lumpur to Langkawi was cancelled, leaving us stranded in a terrible one-star motel for the night. But that unexpected detour led to five incredible days in Langkawi, which, despite the mishap, became one of the highlights of the trip.
Because we had booked cancellable accommodation, we never felt obligated to travel somewhere that wasn't safe or no longer fit into our plans.
Internet Connectivity
Over 100 days, we were constantly crossing borders, and having reliable internet access on our phones made a huge difference. It helped us find our way around busy cities using Google Maps, book accommodation and stay in touch with family back home.
For connectivity, we used Airalo eSIMs throughout the trip and had an excellent experience. It's the only provider we tried, so I can't compare it to alternatives, but it worked reliably in every country we visited. It was easy to set up and was surprisingly inexpensive as you could choose a variety of different plans to suit your needs.
If your phone supports eSIMs, it's worth looking into before you leave.
Money Management
Gone are the days of travellers' cheques and carrying huge wads of foreign currency around the world, but managing your money while travelling still requires a bit of planning before you leave.
You'll want a debit card that allows you to withdraw cash from local ATMs without excessive fees, as there will always be situations where cash is still needed.
A credit card with no foreign transaction fees can also save a meaningful amount over the course of a long trip. Many credit card issuers charge an additional 2.5% to 3% fee on purchases made in foreign currencies, which can add up surprisingly quickly when you're travelling for weeks or months at a time.
Our card of choice throughout the trip was the Wealthsimple Visa. It's a completely free card, and the lack of foreign transaction fees made it the perfect choice for international travel, and it worked reliably everywhere we used it, including via Apple Pay.
However.... I'd also strongly recommend carrying at least two cards and keeping backups split between family members. Why do we know that? Because we lost our main debit card in Vietnam and, while it ultimately wasn't a major issue, it could have become a much bigger problem if it had been our only way to access cash.
While much of Asia is becoming increasingly card-friendly, it's still worth carrying some local currency. Street food vendors, market stalls, small family-run businesses, and the occasional taxi often preferred cash.
Getting your banking and payment strategy sorted before you leave isn't the most exciting part of planning a trip, but it can save a lot of stress once you're on the road.
Share the Experience With Family and Friends
One of the best decisions we made was weaving family into our itinerary wherever possible.
During the trip we spent time with family in Thailand, Bali and New Zealand. Those stops provided far more than just free or cheaper accommodation. They gave us a chance to slow down, reconnect and temporarily step away from the pace of travel.
They also became some of the most meaningful memories of the entire journey. My parents in particular had never visited Asia before, and being able to experience countries like Thailand and Bali together made those moments even more special.
When planning your own route, think about whether there are friends or family members living abroad who you could visit along the way, or that could meet up with you along the way.
School and Learning on the Road
One of the first questions people ask when they hear about our trip is, "What did you do about the kids school?"
It's a fair question. A 100-day round-the-world trip with kids doesn't exactly fit neatly into summer holidays and long weekends!
If we wanted to make this adventure happen, it meant taking the girls out of school for an extended period, which was one of the biggest decisions we faced during the planning process.
We didn't take that decision lightly.
Like many parents, we spent a lot of time weighing the pros and cons. Ultimately, we came to the conclusion that while the girls would miss some time in the classroom, the opportunity to experience different countries and cultures offered its own unique form of education.
We didn't abandon school entirely. We built homeschooling into our plans, and tried to maintain some structure throughout the trip. Jess's teacher even asked her to create short travel videos to share with her classmates back home.
We'll share more about our homeschooling approach in a separate post, but looking back, we believe the experience gave the girls a deeper appreciation for the world and a level of confidence that would have been difficult to develop at home.
Work and Taking Leave
Taking months away from your career can feel like a much bigger leap than booking a flight around the world. Questions about job security, finances, career progression, and what happens while you're away are completely natural.
For many people, an extended break means requesting a leave of absence or sabbatical.
For others, a round-the-world trip may coincide with a career change, the end of a role, or a decision to take a break before starting something new.
I remember spending a lot of time thinking about how I would approach the conversation with my employer. In the end, I found that an open, honest, and flexible approach worked well for me.
I gave around 18 months' notice that I wanted to take a sabbatical, which provided plenty of time for transition planning and succession discussions. I was also transparent about the fact that this had been a long-term family goal that we'd been planning for years.
Most importantly, I committed to doing everything possible to ensure my responsibilities were handed over smoothly and that the business would be set up for success during my absence. I think that preparation and flexibility made it much easier for my employer to say yes.
Not every request will be approved, but you'll never know what's possible unless you have the conversation.
Sort Out Your Home Before You Leave
One of the less glamorous parts of planning a long-term trip is deciding what to do with your home while you're away.
That might mean renting it out or selling. Some people choose to leave it vacant, arrange for family or friends to check in periodically, or hire someone to look after the property. Every situation is different, but it's worth thinking about well in advance.
If you have pets, you'll also need a plan for their care while you're travelling. Depending on the length of your trip, that could mean asking family members for help, arranging long-term pet sitting, or boarding them.
In our case, we were fortunate to have friends periodically check on our home while we were away, and a reliable dog sitter that we have known for years.
Beyond the house itself, don't forget about all the smaller details. Think about mail forwarding, utilities, insurance, lawn care, snow removal, vehicle storage, and any subscriptions or services you may not need while travelling. There's also the question of what to do with your belongings, including furniture, seasonal clothing, and the general accumulation of "stuff" that most families acquire over the years.
There's a lot more to preparing your home for an extended trip than most people realize!
Visas, Vaccinations, and Travel Documents
While planning destinations is the fun part, it's important not to overlook the administrative side of travel.
Entry requirements vary significantly from country to country, and they can change over time. Before booking flights, make sure you understand visa requirements, passport validity rules, and any other entry restrictions that may apply to your nationality.
If you are dual nationality like us, it's worth considering which passport you choose to use, as in some countries the fees were different between our UK and Canadian passports.
The same applies to health preparations. Depending on where you're travelling, certain vaccinations may be recommended or required. If you have a daughter who is petrified of needles (like we do!), you'll find it helpful to review your itinerary several months before departure and speak with a travel health clinic well in advance to ensure everything is sorted before it's time for the jabs.
It's also worth checking whether any prescription medications require additional documentation when crossing borders and confirming that your travel insurance covers all of the countries you plan to visit.
None of this is particularly exciting, but investing a few hours in preparation can help you avoid unnecessary stress and unpleasant surprises once your trip is underway.
Planning a Round-the-World Trip With Kids - Final Thoughts
Looking back, the process of planning a round-the-world trip with kids took considerably longer than the trip itself, but every evening spent researching, every spreadsheet, and every slightly overwhelming conversation was worth it.
Whether you're considering extended travel, a gap year, or a family sabbatical, there's no substitute for good planning. At the same time, not everything needs to be mapped out in advance. You just need to be flexible.
This post is intended as a starting point. Over time, we'll dive deeper into each of these topics, including the true cost of our trip, how we approached homeschooling on the road, what worked well, and what we'd do differently next time. You'll find links to those articles throughout this guide, and we'll continue updating it as new posts are published.
We're a Calgary-based family that travelled for 100 days, documenting each step so other families can get an honest, real-life look at long-term travel with kids.
You can browse the full 100-day daily diary contents list here.