Being banned from Thailand made me realize I need to pay better attention to even the smallest details when traveling.
I traveled for the first time when I was 12 years old. My mother is from Mombasa, Kenya, and wanted my brother and me to meet our family and experience our Kenyan heritage. She sent us as unaccompanied minors from Chicago to Kenya, where we stayed for two years.
That trip instilled a love of travel in my soul. I started traveling again as an adult at 21 years old. I’m a business owner who owns a consultancy. An event in Sydney, Australia, invited me to speak, and I almost broke my keyboard typing, “YES, I’m in.” I got to fly on Virgin Atlantic for the first time, where a bar was in the middle of the Upper Class. From that first trip at 12 to taking pictures in Sydney Harbor at 21, travel has been a way of life—I’ve traveled to 88 countries thus far. I’ve taken trips as part of my business, for pleasure, and some that combined both.
In 2019, after our last child left for college, my wife and I sold all our material possessions to become full-time digital nomads. We’ve lived in Rome, Lisbon, Nice, Medellin, Tokyo, Kuala Lumpur, and the Dominican Republic.
We’ve done meticulous research on being accurate with visas, entry and exit requirements, what we need to know about the countries we’re traveling to, and any other details we need to know as we’ve traveled full-time.
When I tell you I’m a travel expert, I say it from a place of experience. So I should have known better when I made it to Thailand.
The Mistake
I planned to spend six months traveling throughout Asia from July to December 2023 as I scouted a new possible long-term home base. On arrival in Thailand, I was issued a 30-day visa. I did not apply for this visa beforehand and planned not to stay more than 30 days.
When I looked at the dates on my passport, the stamp said July 30 to August 30. I left Pattaya airport knowing I had to leave Thailand before August 30. My wife joined me halfway through my 30 days, so she had more time on her visa.
Our time in Pattaya was amazing. We walked to the beach every day, as it was less than a 10-minute walk from our $400-a-month Airbnb. We soaked up the Southeast Asia heat and enjoyed the cheaper cost of living. We ate delicious food that was never more than $10 a meal. We spent hours walking the two impressive malls near our Airbnb.
Pattaya, Thailand, ended up not being a place we could call “home,” but we had the best time. After our time was up, we headed to the airport for the next leg of our journey: Kuala Lumpur, Malaysia.
We got to immigration at the Pattaya airport, and my wife got through quickly. On the other hand, I waited for what felt like an eternity as the customs agent stared at the screen and called over other immigration agents. They were chatting excitedly.
After the commotion, the customs agent told me I had overstayed my visa and might be arrested. After traveling to 88 countries, I’ve never overstayed a visa, and this moment was beyond scary.
The Lesson
The issue was that July 30 to August 30 was 31 days—not 30. I was taken and held in a separate immigration area for hours with a lot of uncertainty about what would happen.
I was thoroughly questioned about what I did in Thailand and why I overstayed my visa. The customs agents told me Thailand was sick of digital nomads overstaying their visas and not following the rules. I explained that I miscounted the days—this was not something I had done intentionally. I was not paying attention, and I was sorry.
I was eventually told I had to write a letter explaining why I overstayed and saying I’d never do it again. I paid a fine for overstaying and was banned from returning to Thailand for six months. My passport was stamped with an overstay violation.
I was allowed to leave after hours but was shaken as I went. The uncertainty and fear I experienced were vivid life lessons.
The Devil Is in the Details
I’m a full-time traveler, but being banned from Thailand made me realize I need to pay better attention to even the smallest details. The details matter and could be the difference between an amazing travel experience or being banned from a country.
It’s been over a year since the incident, and I’ve since traveled to Japan, Malaysia, the Dominican Republic, Ireland, Amsterdam, Spain, France, and England. I’ve not overstayed my visas in any of the countries.
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