Colombia to Trinidad: Take a Flight or Go Overland?

Due to visa restrictions, I unfortunately have to leave Colombia in December. Their immigration rules dictate that you can only stay six months per calendar year as a tourist here. Instead of trying to explore a new country for just a month, I thought it would be easier to head to Trinidad and Tobago. I fortunately have family in this beautiful Caribbean country and I’m looking forward to the brain break from planning, packing, buses, hostels, and backpacking in general.

Trinidad beaches in Trinidad and Tobago
how I long to revisit this gorgeous secret beach in Trinidad

The destination is not the difficulty; it’s the means of arriving. Colombia is a bit out of my budget, and so I’m financially disabled at the moment. Even though Trinidad and Colombia are super close on the map, there are no direct flights. I have to go through Panama or Miami, and a round-trip ticket will cost me about $500. Yikes!

I prefer to travel overland, and that’s why I’ve only taken one flight since I arrived in Guatemala in February. However, traveling overland and water to Trinidad would mean crossing through Venezuela.

I’m a pretty fearless traveler. I don’t look like an obvious tourist or foreigner thanks to my universal skin tone and facial features, so I’m not marked as a target to rob. I imagine it would be most difficult for a non-Spanish speaker, a traveler with a disability, or an inexperienced backpacker to make the cross. However, I have heard so many negative things about Venezuela from other travelers and bits online that I’m fairly nervous to cross the entire country, from the Caribbean coast of Colombia to Guiria, the port town in Venezuela, by myself.

So I’m asking you guys for advice. What is the real deal in Venezuela? Will I be subject to frequent bus stops and police exploitation? Is crime so high in Caracas that I shouldn’t stay the night? What do you think?

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