Meet Portugal Expert and Insightful Travel Trivia Winner Kellie

by | 21 Jun 2024

I got my mom involved in Insightful trivia, now she is really into it and we get quite competitive on a Tuesday!

Every Tuesday, a global community of curious travellers come together to test their knowledge with Insightful Travel Trivia, our fun online game. 5 questions, 2 minutes, each month a different destination. As a special treat last year during our Portugal Insightful trivia month, a prize of a trip for four on Country Roads of Portugal was offered in partnership with Visit Portugal, and it was travel aficionado and Insightful trivia player Kellie who came up trumps with her Portugal knowledge to scoop the prize.

A keen traveler, American-Canadian Kellie moved around a lot when young for her father’s work, and then just kept going. “I work in performing arts and toured the world for about 15 years and just kept on travelling,” she tells us. I’ve been back home in Canada now for almost five years which is probably the longest time I’ve ever lived in any one place. I feel really privileged to have seen lots of the world, but there’s always more on the hit list.”

We had the pleasure of a chat with Kellie to hear about her win and find out her secrets to success with Insightful Travel Trivia.

Play the game for yourself: Insightful Travel Trivia

Insightful trivia compeition winner smiles in front of a river with a blue sky.

So, Kellie, how did it feel to win the trip to Portugal?

“It was very exciting; I never win anything! But at the same time, I was a little suspicious having done so much cyber security training at work! Even though I had done the quizzes for travel trivia so recognized the name on the email, I made sure I did not click on any links and wrote back to confirm!

“I asked, “excuse my cynicism but I never win anything, is this real?” And the reply came back “yes it’s real.” I was thrilled.

Do you know who you are taking with you?

“I’m taking my mom. She retired in December 2019 with the intention of travelling just before the pandemic struck. So, we have a deal that we’ll travel as much as possible together.

“And then my two work besties are coming with me. I showed them the email at work, and then it was great to be able to say “so when are we going to Portugal?” They were so excited, and we are now counting down the days to the trip in March 2025.”


So how did you get into Insightful Travel Trivia?

“My mum and I took an Insight Vacations tour; the small group Alpine Christmas Markets this past December. When we first signed up for the trip we also signed up for the emails and one of them introduced Insightful trivia.

“Now i’m a quite inquisitive person. My first undergrad degree was History in Theatre and that fueled my thirst for knowledge. I read and read about anything historic until I had a bookshelf of books. So, when it came to the Tuesday travel trivia questions, I had a go and thought they were really fun.

“I did all the Portugal ones and then I got my mom involved. Now she is really into it and we get quite competitive on a Tuesday!”


How are you scoring?

“I get I average about three out of five every week on Insightful trivia, some weeks better than others. I think it helps to already know the destination well, but also depends on if you have strengths in geography or history for example. I also use the Instagram posts, videos and blog articles for clues, that are linked each week to the trivia subject. It depends on how much time I have that Tuesday to play!”

Tell us more about your tour with Insight?

Alpine Christmas Markets was an unforgettable trip. Our tour started just after half of Europe got dumped with snow last December. My mother and I had already arrived in Munich earlier in the week so we didn’t have to worry about all the travel headaches that can go with heavy snow. We just got to experience the magic of the city blanketed in white, it was really special.

“We took a horse carriage ride in Austria and even the drivers were stopping and taking pictures because it never snowed this much! We had such a great time and Greg, our Travel Director was phenomenal.”

Insightful trivia competion winner stands in front of a church in the snow on Alpine Christmas markets tour


How do you usually prefer to travel?

“I travel with family, I travel with friends. I have no qualms solo travelling. Planning every minute is not my vibe – I like to have a couple ideas of things we definitely want to see or do. But I love to just be free to say ‘that street looks cool, let’s see where that takes us. Or, read a blog and be able to say yes lets go and do that.”


So, as a free spirit, how did you find the guided tour experience?

“When we were planning to take a trip together, we knew we wanted a certain amount of help and guidance. But we also wanted a lot of our own independent time.

“A friend of my mum who is a regular traveler with Insight recommended you. We went on to the website, and we loved the fact that while you got to see so much in depth, there was also so much unstructured time.

“When we first met our Travel Director, Greg told us ‘This is your holiday, you can do it however you wish. You can follow the itinerary or just meet us when and where you like’ and we knew it would be great. So, we kind of mixed it up, we did some of the optional experiences and also spent time doing our own thing. So, it was a real good mix.”


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What are you looking forward to most about the trip Portugal?

“I think Portugal is going to be a first for all four of us which is exciting. I once worked on a cruise ship which crossed the Atlantic and we stopped on the southern coast of Portugal, in Faro and it also stopped in the Azores on our way out. But otherwise, Portugal is very much on my bucket list. I have spent time in Macau which is a Portuguese territory, and I loved the vinho verdes and Portuguese cuisine. So, I’m looking forward to enjoying this in its true homeland.

“And then, the UNESCO sites are going to be gorgeous, I’m looking forward to delving deeper into the history alongside all that wine and food!”

Join in the fun and test your worldy knowledge every week with Insightful travel trivia


I'm a writer, editor and interview specialist with a lifetime's love of travel. There’s nothing more inspiring to me than meeting, and writing about, the world's leading destination experts and travel industry insiders. The thing I love most about writing for Insightful is that I'm always learning something new.