12 Most Memorable Trips

This is a blog I’ve been wanting to write for some time, but it’s also something I wanted to do lots of thinking about before I wrote it. How do you distill 196 countries and 30+ years of travel down into 12 trips that were the most memorable for you? What makes a trip memorable? Is it the places? Is it the people? Is it something you did? Or, is it some combination.

Initially, I wanted to keep this to ten most memorable, because everyone likes a Top 10 list. But, I was struggling to get it under 20. I did narrow it down a bit, but in the end, there were really 12 trips that I felt really needed to be told because they’ve formed such an integral part of my travel journey.

That said, it’s obviously not a comprehensive list, and there’s a few honourable mentions that I have to put out there:

• Traveling to Penticton, British Columbia for my first Ironman race
• Spending three weeks traveling the South Pacific and visiting small island nations most people haven’t even heard of like Kiribati, Nauru, and Tuvalu
• Overland from Kinshasa, DRC to Brazzaville, Congo and then to Point Noire, Congo by train and eventually overland to Cabinda, Angola
• First group of Americans allowed into North Korea in decades back in 2005 (you know it’s a tough choice when a trip like this doesn’t even make the list! A photo regardless:

So, with those said, let’s kick off the Top 12 list….in a bit of an order in that #1 is almost certainly the best travel memory I’ll ever had, but other than that it’s a bit random….so please don’t get offended!

#12 – Zimbabwe Coup – End of Mugabe’s Rule

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I’ve been a follower of Zimbabwe for years, going back to grad school when I was studying sanctions. Ever since my first trip to Africa (where the plane actually stopped over in Harare on the way to South Africa) I’ve been fascinated by Zimbabwe and its struggles since Independence.

A few years ago for Thanksgiving I found myself with absolutely no plans when I saw in the news that the military had decided Mugabe’s time as the long-time ruler was coming to an end…and he had “decided” to resign. Except then he went on tv…and did what nobody expected with Generals standing around him: didn’t resign, or even mention it.

Knowing this wouldn’t stand, and I had a five day weekend ahead of me, I booked a last minute trip to Harare, and when I was in the air the military staged a “not coup” and removed him from power. I landed to parties in the streets celebrating hope for the future…which unfortunately has largely proved to be more of the same.

Huge historical moment, and so excited I could be there for it!

#11 First Trip to the Florida Keys

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Despite a year filled with health issues, my amazing friend Jen managed to convince me that “running” 100 miles in the Florida Keys would be something I should do. Health issues continued to be a challenge, so I dialed it back to the 50 mile option (which I could easily walk in the time allowed) before finally deciding the week before not to do the race.

It turned out to be the right call, because having never been to the Keys before I way underestimated the sun, heat, and humidity. That said, I totally want to give it another go in 2020 health permitting.

I did still go down there, which gave me a chance to cheer Jen on in her 100 mile quest and spend time with my friend John who had flown down to be my crew for the race when I thought i was going to do it. Great friends, sun, and gorgeous scenery. What’s not to enjoy?!

#10 Abkhazia

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What do you do when you’ve been to every country? You start “inventing” new ones of course! Not recognized by the UN, Abkhazia is a country that broke away from Georgia a few years back with the support of Russia, and now lives in relatively autonomous peace. Need proof that these “countries” are “worth” visiting? Where else can you:

1. Have lunch at a restaurant called Al Capone’s Pizza where they insist you take pics with toy prop guns and gangster hat
2. See a beautiful lake in the middle of winter where Stalin used to have his datcha
3. Run into a guy walking his bear on the side of the road, only to have him tell you “have bigger one at home”
4. In the middle of a delicious Georgian dinner have a rando drunk restaurant patron start going on and on about his love for Omar Bradley to you?!

So, if that doesn’t convince you that a long weekend in Abkhazia with a great friend is worth it, I don’t know what will!

#9 Kosovo and Macedonia

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I’ve known my friend Dewon for nearly 20 years now, ever since he moved to Washington, D.C. from South Africa for work. His American adventure has taken him all around the country since then (and currently to New York) but we still manage to connect from time to time for amazing adventures.

A few years back he mentioned he’d be in Frankfurt for work and have some time afterwards, so I should pick a country in Europe I hadn’t been to yet (this was 10+ years ago I think?) and we would go for the weekend.

Well, I couldn’t just leave it at one country, and that’s how we ended up flying into Kosovo and eventually hiring a driver to take us to Macedonia. Both were fascinating in their own way: Kosovo because it was still newly-independent and finding its footing as a country, and Macedonia because…well…there were literally statues and monuments everywhere in the capital. It was totally surreal.

Plus, of course, the chance to spend the weekend with a great friend I don’t get to see enough of! Great friends and great times!

#8 Longyearbyen/Svalbard Marathon

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I had always wanted to run the Antarctica Marathon, but it’s a hugely expensive undertaking…with no guarantee the boat will even be able to dock so you can run it. So, what did I do instead? Found the northernmost marathon in the world in Svalbard, Norway way above the Arctic Circle.

On top of being a stunning and scenic locale, it was also by far the smallest marathon I’ve ever run, with less than 30 participants. Unfortunately I got injured about 10 weeks before the race, but recovered enough I was still able to do it at a slow jog and really take in the scenery. Amazing memories!

#7 Saudi Arabia

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Saudi Arabia used to be a really tricky place for “country counters” to check off their list. Unless you got invited there for work, or are Muslim and went on the Hajj, the country was completely closed to tourists. A few people have managed transit visas over the years, but I had to be content with an epic airport story (which I only tell in person over drinks) for my every country visit.

In late 2018, the Saudis announced a limited one-time-only tourist visa for a Formula-E Race that was coming to Riyadh, and country counters descended on Saudi en masse to take advantage of it. Sure, in the meantime the country has opened up even more to the point just about anyone can go at just about any time, but we didn’t know that back then. It was just dozens of country counters taking advantage of what they thought might be a one-time opportunity.

The cool thing about the whole thing was: as cool as Saudi itself was, the people were even more amazing. It was like finding a whole world full of people that “get” you, and understand why you do what you do, and why you travel to the places you do. I made many good friends out of the trip – people I still talk to frequently today.

I’d go to the “Edge of the World” with these people…and quite literally did!

#6 First Round-the-World – 40 Days for 40th Birthday

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Believe it or not, back when I was at just under 100 countries visited I still hadn’t done a true round-the-world trip, where you cross both oceans basically continuing in one direction. So, I decided for my 40th birthday I would book a 40 day round-the-world trip that would be epic in its scale! What was the rough itinerary, well, something like:

1. Aruba, Curacao, and Bonaire
2. Venezuela, Colombia, and Panama
3. Hawaii, Micronesia, the Marshall islands, and Guam
4. quick stops in Japan and Thailand en route to:
5. South Africa, Lesotho, Swaziland
6. Zambia, Zimbabwe, Namibia, Botswana: Victoria Falls!

Tired yet? It was an exhausting and amazing trip, and an unforgettable way to celebrate four decades on this planet!

#5 Johannesburg for U2 PopMart Concert

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For me, this is where it all really started.

Sure, I’d been to the Soviet Union and a few trips to Europe. Less than ten countries total, but then came the opportunity to see U2 in Johannesburg for the final concert of the PopMart Tour, and when my friend Matt (as anyone who knows me knows – it’s ALWAYS a Matt) said he was game for it…a plan was hatched.

My first time in Africa, first time outside Europe and North America, and I was absolutely addicted to travel. If I could pull this off, I could do anything! It would take a few more years until I had the time and money to really start ramping up the travel, but once I did there was no stopping me.

I have U2 to thank for my love of music (I was at the original Red Rocks concert – the best thing about divorced parents who hear about these “cool new bands kids are into” and take you to a random concert) and have seen them all over the world now.

I can still pretty much see the entire concert in Johannesburg as vivid as if it was yesterday (despite being more than twenty years ago) and to this day when I go back to Johannesburg I always stay in the same hotel that I stayed in 20 years ago on that first trip. For me, it really was the trip that started it all.

#4 Dominican Republic

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They say that true friends show it when you need them most. After ending a ten-year relationship I was more than a little bit of an emotional mess, and really needed something to get my mind in a better place and start moving forward again.

As luck would have it, my close friend John was headed to the Dominican Republic the next week (a country which at that time I still hadn’t been to!) with a group of 20+ friends, and pretty much insisted I join them. Anyone who knows me knows I’m very anti group trip, anti resort, anti cruise, blah blah blah, but I’m very glad I went on this trip!

I made some absolutely amazing friends, it was exactly what I needed at that point in my life, and despite just meeting all these new people they were really there for me over the coming years as I moved on and figured out my next steps in life!

Shout out to my Ottawa family for being there – and being amazing people!

#3 Easter Island

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Continuing the theme of things to do when you’ve been to every country, I found a great fare to Chile a couple years ago, booked it for a week, and figured I could decide what I would do later. I had only spent a couple days in Chile my first trip, so really wanted to explore more.

Well, my friend Phil who recently moved from DC to California was up for joining, and together we hatched a plan to visit Easter Island…where we actually spent several nights sleeping in a geodesic dome! I’m normally the type to opt for posh hotels, but yes, I pretty much roughed it for several days there…and loved every minute out in nature!

Everyone knows Easter Island for the Moai statues, but what you probably don’t know is it’s also home to amazing food and some of the freshest fish I’ve ever had. I would love to go back and spend a week again – this time maybe doing more hiking all over the island!

#2 Soviet Union

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When I was 17 I left North America for the first time for a four week study trip…to the Soviet Union. Yes, my first time out of North America was to the USSR! Probably proof I was destined for off the beaten path from a very young age!

My school didn’t have a ton of language options, and I had pretty much outgrown them by 11th grade so I had started spending summers at a Russian language camp to get more of a challenge. When they offered a trip over Christmas and New Years to the Soviet Union I begged and pleaded with the parents who were surprisingly ok with the idea, and off I went.

I went into the unknown with absolutely no idea what to expect, and although I dialed it back for the next few years (since I still had to learn how to travel independently and not in a school trip) I think this is what convinced me that I wanted to see more of the world.

“Weird” foods (I still remember the aspic for dinner on the first night and the joy my host family took me in serving pomegranates and coke in the middle of winter), strange customs, and not to mention “communism” (psst. mister, you have jeans? Buy rabbit skin hat?) it was all strange and so very foreign to me…and I loved it!

We spent four weeks in Moscow, Leningrad, Kiev, and Novosibirsk, and I wanted more! Strangely, it would be nearly 25 years until I would return to an independent Russia, but all the memories came flooding back. I can’t find the pictures from 1988 (hopefully I’ll find them in a box somewhere eventually) so I’ve included some of my Moscow, St. Petersburg, and Novosibirsk pictures above.

#1 Iceland – 196th (Every!) Country Visited

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So, this one is probably pretty obvious! What better way to celebrate visiting every country than to hit your final country with more than 30 friends and family for four days in a gorgeous place like Iceland! It was truly a special and wonderful time and meant a lot to me that all these people I had spent so much time away from as I ran around the world were all willing to come to Iceland to celebrate with me.

From our guided walk around Reykjavik to a silly afternoon at the Blue Lagoon, to a day with SuperJeeps around the Golden Circle I think I pretty much spent the entire trip with a giant smile on my face…well, except maybe the hour I spent getting the unplanned “Iceland 196” tattoo to celebrate the achievement!

Is it terrible I’m secretly hoping someone else declares themselves independent in the next year so we can have a #Jason197 party somewhere for my 50th birthday?