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How it All Started

As you can imagine it takes alot of planning to fly around the world. Before the planning even started, we as a family had to discuss how it was going to work. 

Ian (our Dad) has been a pilot for 4 decades and always dreamed of flying around the world. He has previously took part in a few longer flying expeditions for charity and always thought it would be nice to stay a bit longer to get to know an area, and if you're staying longer, it would be nice to have your family around.  So our dad came up with the idea to fly around the world, low and slow, stopping in to get to know a region. He ran it by Michelle (our Mom) first then we sat down as a family to talk about it. We (the kids) had a bunch of questions about how it would work but we talked it all through and the planning started. And that's how the 5intheSky expedition was born! 

How it Stated

Meet Our Crew

Ian Porter

Ian Porter

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60 Years Old - He/Him

Taking a time-out from a successful career in real estate development, Ian is the “Chief Pilot” and Team Leader for the expedition. He’s flown paragliders, paramotors, sailplanes and fixed wing aircraft in many places around the world for the last 4 decades. With a BA (Sc) from the University of Western Ontario and an MBA from Queens University at Kingston, he has started, grown and sold a number of companies. Married to Michelle for 24 years now, they have travelled together, and with their children, to many countries.

Sydney Porter

Sydney Porter

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18 Years Old - She/Her

Sydney has graduated grade 12 French immersion at a public high-school in Vancouver, and has a keen interest in STEM – Science, Technology, Engineering and Math. She is always a whirl-wind of energy and is active in soccer, field hockey, snow-sports and is a black belt in Shotokan Karate – a sport she has practiced for 10 years now and competes in nationally and internationally. Bilingual in French and English, Sydney is also a licensed Private Pilot and will often sit “right seat” as co-pilot or as PIC during the expedition. Sydney will take a gap year prior to entering university to participate in the expedition.

Michelle Porter

Michelle Porter

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59 Years Old - She/Her

On the expedition, Michelle will continue in her role as mum, medic, counsellor, logistics coordinator, communications coordinator… get it. Early in her career and prior to becoming a full-time homemaker, Michelle worked at UBC within the Centre for Health Services and Policy Research in Epidemiology, then branched into Technology Transfer and the commercialization of biotech intellectual property. She then joined a major Biotech Research & Development firm. Michelle is one of the happiest and positive people you could hope to find and has shared many memorable travel adventures with Ian and their family.

Samantha Porter

Samantha Porter

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22 Years Old - She/Her

Samantha has completed her 3rd year at the University of British Columbia (UBC) studying Geography –Environment and Sustainability. An accomplished athlete, Samantha’s energy and enthusiasm motivates people on any team she is on to just try harder. Soccer is her sport of choice, and she has kicked the ball around in friendly play with kids in far flung places such as Ecuador, India and Tanzania. Bilingual in French and English, Samantha is also making progress with conversational Spanish. She is a licensed Private Pilot and will often sit “right seat” as co-pilot or fly pilot-in-command during the expedition. Samantha has put her UBC studies on hold for a year to participate in the expedition.

Christopher Porter

Christopher Porter

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15 Years Old - He/Him

Christopher is in Grade 10 at a public French immersion school in Vancouver, which he will continue online while participating in the expedition. He’s smart, witty and athletic and enjoys soccer, rugby, snow sports and paddling C1 Canoe and K2 Kayak. He was too young to remember some of the countries he has previously been to, so is looking forward to getting re-acquainted with them.

Meet our crew
The Dynamic

Who Does What?

While we have lots of fun, this is not a vacation, it is an expedition. Flying yourself around the world in a single engine aircraft, completely VFR takes a lot of work and responsibility. We are more than a family, we are a team. If you say you are going to do something, it better be done to the best of your ability. Unlike driving a car or sailing, with flying there is no brief pause, or pulling over. To make sure everything gets done or has someone thinking about what needs to get don we have devised key roles and responsibilities. While the full list is much longer, here is a very general example of only a few of each team members responsibilities:


- Chief pilot & Team Leader

- Safety Coordinator

- Airplane maintenance


- Health documents & Visas

- Food and snacks

- Day to day necessities (ex. Laundry)


- Co-Pilot

- Social Media Management

- Ground Transport & Communications


- Co-Pilot

- Website Management

- GenDecs and Travel Documentation


- Drone Operations

- Camera equipment 

- School

These are general ideas, and do not nearly cover the extent of work that has to be done. These categories also don't mean that one person does everything by themselves, it's just an example of an  area that they are responsible for, whether that means making a plan for it, doing it yourself, allocating it or just keeping it int he back of your mind. There is always more to be done!

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