Having returned a couple of weeks ago from an epic family adventure around the world, several people asked about the 13 country itinerary so I wanted to share the details.
The trip was triggered months ago with speeches I needed to deliver on July 26th and 28th in Cairns, Australia for ARN Edge 2026 on the future of channel partner ecosystems. A summary of the speech can be found here.
The idea was similar to another round-the-world adventure from before the pandemic (2019) that, with Michelle and the kids, dropped into 15 countries. Basically, to meander our way around the world with a bunch of shorter flights ending up in Australia at the end.
With now heavy use of AI tools such as Gemini and ChatGPT, alongside favorites like Kayak.com and Hotels.com, we kept the trip as flexible as possible and in many cases would only book the hotel room the day of staying. This caused a bit of anxiety at times, but also saved money without keeping to a rigid schedule. The days of having to book anything multiple weeks/months in advance is long over.
This trip also extends the original bucket list "100 Country Rollerblades and Red Bull Tour".
While the rollerblades and Red Bull have been curtailed in recent years, the march to 100 continues was finished on our Africa trip and now has me at 112 countries!
Planning for this trip had 3 distinct parts:
1. The direct flight from Miami to Rome, with a rental car taking us 4,000 kilometers across Europe. From an overnight ferry down to Sicily (Michelle's ancestral home) up to Venice, Switzerland, Liechtenstein, Austria, Munich, Prague and then over to Frankfurt.
2. The exploration of the heart of the Silk Road through Central Asia including Uzbekistan, Kyrgyzstan, and Kazakstan.
3. Exploring China, and then over to Tokyo to get down to Cairns, Australia for the speeches.
Each day of the trip brought lifelong memories, but also incredible challenges (that don't show up on glamorous Facebook posts) that I will talk about at the end.
--> Exploring Rome and the Vatican for the first time with the kids
--> The shocking history of Pompeii and the absolute beauty of Positano.
--> The incredible beauty of Michelle's ancestral home in Ragusa, Sicily and driving around the entire island after an overnight ferry from Naples.
--> The loooong drive from Sicily up to the stunning Venice for a day (and night) on the canals.
--> Cali really wanted to see Switzerland and I wanted to stop in Liechtenstein (a small country I missed on my 14-country tour a long time ago through Europe).
--> We continued to drive north through Austria and Germany where we saw the castle that inspired Walt Disney for his princess castles at Disneyland and Disney World!
--> Michelle had never been to Germany and I would always say that, after visiting 112 countries, that Prague was a magical place for me on a previous trip. It was on our "must see" list.
--> After 4,000 kilometers of driving through Europe, it was now time for Part 2 of the trip through Central Asia - the Stans! First stop direct from Frankfurt was Uzbekistan and a 2-hour train ride over to Samarkand.
As one of Central Asia's oldest continuously inhabited cities, Samarkand is historically significant as a pivotal crossroad of the Silk Road that connected trade and culture between East and West, and as the grand capital of the 14th-century Timurid Empire renowned for its landmark Islamic architecture.
--> The second country on the Stan tour was Kyrgyzstan - a landlocked Central Asian nation defined by the towering Tian Shan mountain range, a rich nomadic culture rooted in ancient Silk Road history, and a strong tradition of oral storytelling.
--> The final country on the Stan tour is the 9th largest country in the world by land mass, Kazakstan. It is a vast Central Asian nation characterized by its expansive steppes, rich oil and mineral wealth, and a deep nomadic heritage bridging East and West.
--> After the Stans, it was time to start moving East again. Next stop, Beijing.
With over 3,000 years of history, Beijing has served as the imperial capital for multiple ruling dynasties, including the Yuan, Ming, and Qing, shaping it into the heart of Chinese civilization.
Today, as the political and cultural capital of the People's Republic of China, it stands as a global superpower hub that bridges ancient heritage, like the Forbidden City and Great Wall, with modern innovation and international diplomacy.
--> It was now time to make our way to Cairns, Australia. A quick stop in Tokyo before heading south. We were able to rent another car and see some breathless scenery before the ARN event got into full swing.
Cairns serves as the primary gateway to Tropical North Queensland, renowned worldwide as the departure point for exploring the Great Barrier Reef.
Beyond marine adventures, the region attracts visitors with its ancient tropical landscapes, highlighted by the UNESCO World Heritage-listed Daintree Rainforest, scenic coastal drives, and yes, lots of crocodiles!
--> After all of this adventure, it was time to put on a sport coat that I had been lugging through 13 countries, and get up on stage.
ARN (Australian Reseller News) is the premier news publication for the Australian IT channel, while EDGE is its flagship annual conference gathering ICT vendors, distributors, and managed service providers to discuss ecosystem growth and market strategies.
--> We flew from Cairns to Sydney to Dallas and then to Miami back-to-back. The only flight delay (only 2 hours) on the entire worldwide trip came on the Dallas leg and then they lost our luggage which took 5 days to resolve.
We were home so it really didn't matter, but that brings up an important point about traveling challenges. They happen almost every day on a trip like this - some small and forgettable, some large and will be remembered forever!
So here they are...the challenges:
1. We were robbed in Switzerland!
Of all the places we have been - from Antarctica to Africa - who would of thought that Switzerland was the place that could of ended our entire trip with a robbery of our passports?!
It was surreal experience.
Walking back to our rented SUV in Lucerne after a few hours of sightseeing and lunch, I saw a vehicle with its trunk open and a bright yellow Porsche suitcase just like mine. I thought, wow, that guy has the same suitcase as I do.
He then turned around and had a red Ducati backpack on. I thought, wow, he has the same motorcycle as I do too!
Then it clicked.
My ten year old (Cali) said she has never heard me curse before. The guy saw us and started running. It then dawned on me that our 4 passports were in that bag! The entire trip would have to be cancelled (in country 2 of 13) and we would have had to come straight back to the US.
So I defaulted into my Canadian hockey player mode and gave chase. Weighted down by the backpack and a bunch of coins he must have been stealing from every car, it didn't take long to catch up.
I tackled him in the middle of the street. Coins went everywhere. The backpack came off. A key from around his neck ripped off.
Cali jumped into action and took off with his key.
His face then turned really serious as that key would determine whether he got away or went to jail. He started to swing at Cali and lunging at her which caused her to fall down. He started to reach for his waistband too.
With our passports back, I yelled at Cali to throw the key and jump to safety. The police came, people came out of their shops, drivers stopped in the middle of the street - it was quite the scene.
The police (and locals) were horrified this happened in their town and were so apologetic. Because this involved a child, the severity of the punishment goes up by 5X in Switzerland. They promised to watch every camera on every street light and make an arrest.
We got to move on to Liechtenstein.
2. My ATM card was sucked into an ATM machine in Uzbekistan
In the category of "all my fault", I lost focus for a moment and impacted the rest of the trip in ways I didn't imagine (or plan for).
After 112 countries, I have a rule that I go to the first ATM that I see and withdraw the equivalent of US$100 in the local currency.
I was surprised when the machine spit out $1,000,000 in Uzbekistan dollars and I turned to the kids to wave a stack of $100,000 bills!
The machine started to beep and when I turned around the card was sucked back in. Calls to the bank told us it would be 3 or 4 business days to get it back and we were leaving in 48 hours.
I had a backup card to a Canadian account but the card wasn't used in 6 months so they terminated it. Our credit cards all have PIN numbers for cash back but we didn't know any of them. My corporate card doesn't support cash back.
So, Central Asia, still half a dozen countries to go, and no access to cash in places without good credit card infrastructure.
The solution was Western Union, but explaining to Russian banks (The Stans were part of USSR until 1991) in Russian language that I am sending money to myself and "trust me" was difficult. A few banks turned me down while angry, unpaid, taxi drivers waited outside.
I finally got $500 in USD and protected that like it was gold for the remainder of the trip!
3. Michelle got her iPhone stolen in a train station, also in Uzbekistan
Also in the category of "our fault", Michelle left her iPhone in a bathroom stall at a train station. Her pictures, navigation, communication and payments, gone.
It was only about 30 seconds later when she realized it was missing and rushed back into the bathroom. No one claimed they saw it and the cleaning lady said she was out of luck.
I hit the Apple Find My iPhone feature and the phone started ringing - right in the middle of the cleaning lady's stuff. She had hidden it.
Crisis averted but it made us question humanity for a moment.
Other challenges were not as serious but still added unnecessary drama:
--> I booked the car from the wrong Rome airport. D'oh. While they are only 19 miles apart, the travel time was close to an hour. The first airport had a lucky cancelation and a nice MG SUV to rent but it could have started the trip with a thud.
--> Our first night away from Rome in Positano was a Airbnb type hotel up on a high cliff with a promise of a lock box number that never came. We were sitting at a restaurant at 11pm trying to get the number still and contemplating if we were sleeping in the car.
--> I lost my Meta Oakley glasses on the Great Wall of China. With memories of Michelle's iPhone, I was questioning if I would ever see them again. Interestingly enough, our tour guide said that very little theft happens in China because of the overly severe consequences. We walked back and the first tower guard had the glasses from someone who turned them in. Faith in humanity restored!
--> We had couple of challenges in China that we should have planned better for. First, our phones (Verizon) didn't connect to their network. No cell phone access meant no two-factor authentication on our credit cards. AliPay, their version of an "everything app" worked great till we hit $1000 and then the fraud checks started to come. We could verify any of the cards and were stuck with our tour guide paying for everything. Luckily he had an old PayPal account (through a VPN because it isn't allowed in China) and we were able to get money (and a big tip) over to him.
--> Flight delays to Dallas and they lost our luggage for 5 days. The trip around the world through 13 countries was flawless. Every flight was on time and our luggage was sitting at customs waiting for us. That was until our trip home and we faced a 2-hour delay. That then meant that only 1 out of our 6 bags showed up in Miami. Five days later it was resolved. It didn't really matter because we were home, but still another small stressor.
All in all, the trip was fantastic. The memories will be there for a lifetime.
It also reminded ourselves that we have become a bit too lax on our planning. Not carrying enough cash. Not testing cards before we go. Not researching enough of the gotchas in far away lands. We will remedy this for next time.
Onward and upward!
