20 Highlights of My 20s

Click HERE to Read from the Beginning.

14. New York

After having no interest in visiting New York for a number of years due to my perception of it being a large and unfriendly city, I finally made a trip there and was very pleasantly surprised. I have always enjoyed smaller towns and villages and have had less interest in large cities, but I found New York to have an incredible amount of culture and class and it has now become one of my favourite cities in the world.

I was lucky enough to have a friend living in Manhattan and was able to spend a long time couch surfing without cost. Wanting to make the most of my New York experience, I took all that money saved on accommodation and poured it into fine dining and entertainment. I went to a New York Rangers playoff game at MSG, Brooklyn Nets game, Yankees game, and a number of top bars and restaurants in addition to the usual New York tourist sites. You can read more about my New York experiences HERE.

15. Living in Dubai

When Yemen’s security situation degraded in 2011 as part of the ‘Arab Uprising’ across the Middle East, my company decided to move me to Dubai, to work out of their Free Zone (DAFZA) office, and live at Le Meridien Hotel near the airport. There were even a few nights where I was even put up in the Jumeirah Emirates Towers, an expensive world class hotel.

There were some negatives to living in a hotel for a year, but overall it was a wonderful experience. Usually when I stay in a hotel I am very cognizant of the costs. In this case, my company decided it would rather pay my expenses than a per diem (something I will never understand), so I made the most of it. For breakfast, lunch, and dinner I was enjoying room service or restaurants and of course it was nice having my bed made each day, complete with turn down service. After a while, all of the staff knew me by name and before too long I knew many of them quite well too. I am sure when I walked the halls with people they wondered who I was and why all of the staff knew me – the closest to a ‘pretty big deal’ I have ever felt.

While in Dubai I got to know some Emirates Cabin Crew, which is practically like finding the keys to the city. They know where to go, what to do, and always have interesting stories from their travels. I also got involved in the Couch Surfing scene and organized a fun event at The Warehouse restaurant where I met some wonderful people. While Dubai was an unexpected home for a year, it certainly was a great year and one that I will look fondly upon for the rest of my life. You can read more about Dubai HERE.

16. Road Trip to the Arctic Circle

I have always wanted to visit the Arctic Circle, as well as explore Northern Canada. Thanks to my uncle, who is a university professor, inviting me to join him on his visit to Inuvik where he was asked to lecture, I finally had the perfect opportunity to do so.

We drove to Inuvik and, despite the many hours spent in the car, the experience was incredible. The scenery in Northern Canada was very impressive and we were also lucky enough to see wildlife including numerous grizzly bears. You can read more about my road trip to Inuvik HERE.

17. Balkans

I remember watching the Bosnian War on TV when I was 8-11 years old and the images of burning buildings and tanks in the streets probably formed my earliest memories of war. When I finally visited the former Yugoslavia in 2013, I was pleasantly surprised and amazed at just how beautiful and wonderful the region is.

In Serbia, Bosnia, Croatia, Montenegro, Albania, and Macedonia, the scenery was majestic, the people were genial, and the history of the region provided a number of great learning opportunities for me. I also loved the fact that touring the Balkans was relatively easy, yet many of the countries are not very touristic. When I visit countries that have become too commercialized and lost their ‘soul’ I am always upset that I was too late. With many of the Balkan countries I feel like I arrived at just the right time and I look forward to returning again before tourism develops much further.

I was also lucky enough to travel through the Balkans with Sara, a girl I met through Couch Surfing in Dubai. After meeting Sara, I have enjoyed the privilege of traveling with her to Spain, Croatia, Montenegro, Macedonia, Albania, Greece and Ethiopia. Her company certainly made all those trips more enjoyable and memorable and I feel blessed to have found such an amazing travel partner. I am greatly looking forward to traveling and spending more time with her in my 30s!

18. Solo Backpacking Adventure through Cambodia & Vietnam

My first trip with no real pre-planning was through Cambodia and Vietnam. I had flights booked into Siem Reap, Cambodia, and flights booked out of Hanoi, Vietnam, around a month later. Everything else was left to on the ground planning which allowed me lots of flexibility to tailor my journey as I went.

Unfortunately, due to the nature of my job and fixed schedule I need to strategically plan my trips to make the most of my time off. In this case, I just went with the flow and loved it. The trip itself was a highlight, but I also learned how great it is to have flexibility while traveling and stay with people or in places that you love without any concern over the next destination.

19. Trips with Family

I was fortunate enough to go on several trips with family members, which I will forever cherish. I went to South Africa with my Mom and Aunt, road tripped to the Arctic Circle with my uncle and cousin, drove around Scotland with my parents, cruised the Caribbean over Christmas with my parents, and attended my cousin’s wedding in Mexico with lots of family.

A big part of travel for me is not just where I go but also who I go with. Sharing these wonderful travel experiences with loved ones just makes them all that more wonderful and I feel fortunate that we were able to make the trips happen.

20. Leaving Canada

When I was 28, I made the significant life decision that I want to live internationally forever. Although I love many parts of Canada, I have decided that I am better suited for a low tax jurisdiction where there are fewer rules and regulations that govern my daily life. I have also decided that I do not fit in with North America’s consumer-driven society and would rather live somewhere with less material possessions to experience more culture. Where (and if) I settle remains to be determined, and whether my envisioned lifestyle comes to fruition remains to be seen, but it is a risk I have deemed worth taking and it will certainly be a decision that impacts the rest of my life.

It was surprisingly difficult to narrow this list down to only 20 highlights. I have had a lot of amazing experiences over the last decade and have met a number of incredible people who I wish I could specifically mention. Now, time to get out and create 30 highlights during my 30s!!!