01/20/2026
What I learned about life (and business) running an offshore charter boat in Cartagena, Colombia.
Colombia is one of the most misunderstood countries I’ve ever spent time in.
At 24, I spent several months backpacking through Argentina, Brazil, Peru, and Ecuador before eventually arriving in southern Colombia. I worked my way north and landed in Cartagena. During those travels, I developed a habit: wandering down to marinas, looking at boats, and asking what was for sale. At that point in my life, it was hard to talk to me for five minutes without me bringing up the idea of buying a sailboat and exploring the world.
The idea had a hold of me.
A few years earlier, at 19, I’d bought my first motorboat and learned navigation and chart reading in the Gulf Islands of the Pacific Northwest. I’d also worked on gold exploration and oil & gas drilling rigs around the world, so I was confident troubleshooting mechanical and electrical systems. The one thing I didn’t know how to do was sail. Minor challenge, that is much easier to overcome when you have a boat to practise with.
One afternoon in Cartagena’s harbour, I spotted a “For Sale” sign on a beautiful 34-foot sailboat. The owner, an American in his late 80s, wanted $30,000 USD. The boat was fully set up for offshore sailing: hard top, solar, a near-new engine. It had been “Caribbeanized”. By Caribbeanized, I mean that the sewage holding tank had been removed and replaced with a second freshwater tank. Because there was little to no regulation around this in the Caribbean, it allowed sailors to stay out and explore remote islands for twice as long, since they effectively doubled their freshwater capacity.
However, once the holding tank was removed, the boat could no longer be sailed back into U.S. waters for recreational use or listed for sale. As a result, if you’re shopping in the Caribbean, you can often buy sailboats at 50% of market value (or less) because they’ve been “Caribbeanized” and can’t legally be returned to U.S. waters to sell.
I offered $15,000 USD. Roughly 75% of my net worth at the time. I left my hotel name, and walked away. The next morning, the hotel called my room. He was in the lobby. He’d take the offer.
I bought the boat, registered it in Canada, renamed it Northern Drifter, and quickly realized it was one of the most reckless decisions I’d ever made. I had $5,000 left and needed to earn immediately. I started running short charters to nearby islands. Snorkeling, anchoring, living aboard and charging $30 per night per person and scraping together a living.
The real money, though, was the Cartagena-to-Panama route via the Darién Gap. One of the most dangerous passages in the Caribbean. Sixty-knot winds, violent squalls, 6–8 meter seas offshore, followed by extremely challenging navigation through the San Blas reefs. Entire wrecks litter the route as warnings.
There is no road connecting Central America to South America. Travelers making their way south through Central America either need to fly from Panama into Colombia or find a charter boat to cross. Thousands of tourists move north and south each year and must navigate this geographic bottleneck. As a result, an informal industry has developed where recreational boaters offer charters to earn cash for a few months before continuing their own sailing adventures.
At the time, the cost of a charter crossing was generally $500–600 USD per person. The trip typically lasted five days: two to three days offshore, followed by two to three days anchored in the San Blas Islands. My 34-footer could carry six passengers, and I could comfortably run two trips per month. Roughly $7,000 USD in monthly topline revenue, which was more than enough to live comfortably on a sailboat in the Caribbean.
My ambition was driving me toward that goal. However, my skill set was lacking, and I severely underestimated the risks and challenges of longer offshore charters. On top of that, the realities of operating a business in Colombia quickly came into focus, and I worked diligently each day to overcome those challenges.
In total, I ran the boat for just under a year before selling it for $16,000 USD. I was so shell-shocked from battling offshore storms that after selling the boat, I did little more than look at the ocean for the next three years. No fishing, no sailing, no kayaking. It took time to rebuild my relationship with the water.
Fourteen years later, I still haven’t sailed offshore again. I love the ocean, and there aren’t many days when I’m not on or around it. The only difference now is that I like the weather to be good, and I like to see land.
What it taught me
- The ocean demands respect.
- You can figure things out as you go in business. Never with the ocean.
- Progress doesn’t need to be fast. Steady, incremental growth is enough.
- Ambition without skill is dangerous.
I still carry those lessons with me. On the water and in business.
A blog post from some backpackers I took from Panama to Columbia (one of the safer crossings).
https://www.crazyguyonabike.com/doc/page/?page_id=296931
Challenges and how I overcame them
Regulatory challenges
The Colombian government began cracking down on non-Colombian vessels operating charter routes between Panama and Colombia. A new regulation was introduced requiring each vessel to have a Colombian national onboard and officially listed as the captain.
I eventually connected with an older Swedish captain who had recently shipwrecked his own boat but held a Colombian passport. I brought him onboard and listed him as captain on the vessel’s paperwork for offshore crossings, which allowed us to continue operating legally.
Bribes and bureaucracy
When entering Panamanian waters, captains are required to visit a remote immigration office in the San Blas Islands to have all passengers’ passports stamped. Typically, the captain submits all passports together. If officials see a non-Colombian captain, they often invent arbitrary per-person fees or refuse to issue stamps altogether.
In practice, there was little choice but to negotiate the fee down as much as possible and pay it directly. Money that clearly went into an individual’s pocket rather than any official system.
“Gringo tax”
Throughout much of the region, it’s common for businesses to charge tourists and non-locals higher prices. This applied to nearly everything: mechanical services, transportation, retail, and food and beverage.
When traveling casually, the bartering culture can be enjoyable. But when running a business with recurring expenses, it becomes frustrating, especially when you know the boat beside you is paying 20% less for the same service.
To manage costs more effectively, I built relationships with the marina staff. For any transaction over a hundred dollars, I’d have them make the arrangements on my behalf. Usually a bottle of Colombian rum that cost $3 at the time, was enough payment for this service.
