Jet Lag: The Game

Jet Lag: The Game is a web series on YouTube and Nebula produced by Wendover Productions, where three or four players (Adam, Ben, Sam and occasionally a guest) play a large-scale game involving (usually) public transit, often based on a board game.
It's sort of like if The Amazing Race was good.

Videos (when there's a season running) are released weekly on Wednesday/Thursday (depending on your time zone), with episodes releasing a week earlier on Nebula.

They also run a (Nebula-exclusive) companion podcast, The Layover, which talks about each episode as it comes out.

Who I would recommend it to

Why I like it

I mean, pretty self-explanatory - I fit all of the above categories :3

The trio design all of the games they play, which means the game design needs to be high-quality and have minimal exploits - they'd know of them if they existed.