The journey to Costa Rica was an interesting one. I was nervous with only a 45 minute layover in Houston, and as it turns out, I should have been. Anyone who tells me they have flown out of JFK on time will be the first. I had high hopes for leaving on time when all passengers were seated and the door to the plane closed a full 15 minutes before our scheduled departure time.
The pilot then comes on and says, “Um, folks. There is good news and bad news. The good news is that everyone is on the plane and all systems are go. The bad news is, the baggage loader is broken and they are estimating 30 minutes to resolve it.”
Great! 45 minute layover to catch our next flight in Houston and already 30 minutes late. We end up leaving 45 minutes late and I am nervous about landing in Houston. The good news, there appears to be about twenty people on our flight who are all hoping to catch the connection to Costa Rica.
So we land in Houston (quick side bar, I thought the air in LA and NYC was dirty, Houston’s air makes ours look clean!) and they tell us our plane has been held, but to run. So we run, run, run and barely make the door. On the way in I ask about our luggage and the (lying) service person says “Everything should be fine!”
Long story short, we land in Costa Rica but our bags don’t. This is complicated the fact that we are catching a puddle jumper to the boondocks where our final destination is. Said puddle jumper his here:

We sat right behind the pilots and it was a hoot. It is amazing how many buttons, knobs, and gauges there are. Gotta love too how the flight plan is pinned to the wheel.

The “airport” we landed at was basically like a bus stop. At the end of the very narrow runway was a little shelter . . .

. . . and high tech equipment like this scale.

Funny enough, on our first full day there we ran into someone who was on our flight out of JFK who also lost his luggage. Turns out he was from the Bronx and we ended up hanging out and having dinner. Our luggage finally did arrive, but a massive downpour made things even more complicated.
There were no paved roads where we were staying and if you drive, you have to take a 1 hour ferry to get to where we were staying. Note to self - pack one day worth of clothing in your carry on in the future. In all my years of traveling this was the first luggage mishap I had - guess I rolled the dice one too many times on not being better safe than sorry.