I was just wondering how often has Chris been on vacation?
Apparently, going on a vacation isn't unheard of in the Chandler household. Even after Bob's death, Barb & Chris went to DC for a Mythbusters show. Even the trip Chris took to the Mid-Atlantic Anime convention counts as a vacation since he got a hotel room.
You know, Chris gets a lot of money from the

and I know the Chandlers need the money for upkeep and etc. but if you know where to look, you could find something great to do.
I only make about $500 a month currently (off season) yet I'm just about to go on a Cruise. Found one and it costed $400. Truth is, thanks to cruise ship disasters, less people go on cruises these days and the companies sell tickets for cheap now just to sell them. But of course, unless in the rare event something goes wrong, a cruise could be just the most amazing experience you could do for such cheap dollars. Casinos, sushi, karaoke, the list is essentially endless.
You know, for someone like Chris, it would be fairly easy for him to become an

and go completely unnoticed. Nobody would care to think of the long-haired hillbilly that from first glance is just a common cruiser. Ignore him and let him be lonely the whole trip
If he'd clean himself properly, though, he'd probably be able to fit in as long as he doesn't smash the slots open because they stole his money.