Good advice.The 'Generous Boss' is truly a caring person of the highest order, but: Some employees [or spouses]may abhor that type vacation or destination; some may already have commitments or promises made, some may not be as comfortable comingling with 'boss' & family on a 24-7 vacation, it may put some introverted people on the spot, some employees may be struggling with debt--and desperately need CASH. His heart is certainly in the right spot, but he IS the boss, and should allow that workers may have different perspectives.

Why should the boss feel responsible for his employee's debt? As long as he is making the trip truly voluntary, inviting spouses, and not counting this against their vaction time, no oine has the right to tell him what he must give to anyone. He is already providing them a salary in exchange for their services, which they are free to terminate at any time or to try to negotiate for a better deal.

It always bothers me when people look a gift horse in the mouth. Examples include someone receiving an unexpected gift and complaining that they don't frequent the business that the gift card is for, or that it isn't enough, or that they'd rather have cash than the card or than an opportunity to go to a picnic. The cash-for-picnic option would probably net them less than $15, but the point is, it's a gift. Something no one is obligated to give them, and which they are under no obligation to accept or to use once it is accepted.

If they don't want whatever is offered, politely say "no thank you", give it to someone else, or throw it away. In this case, go on the trip or tell the boss no thanks.

Nothing is ever "truly voluntary" - those who didn't go would be looked upon askance by their co-workers, looked upon as ingrates by the boss (he is after all only human) and be left behind in what for the others would be a "bonding" experience.

My husband is just this kind of generous boss. The deal with his employees is simple, good pay, hot lunch and dinner proveded if your at work, good cash bonuses at Xmas, and when once a year he takes everyone and theiir family on vacation, someplace we can all drive, totally optional, and he pays for it all. Your parents or long lost cousin wants to come? Okay but they pay for themselves. If your married to it, sleeping with it, or spawned it we'll pay for it. Clear enough?

The catch is this, if you don't go on the vacation, you don't get some of the money, we don't care what your debt issues are. It is a perk of the job and you are welcome to take or to leave it. Lunch is the same way, want to go home and see your dog who just had surgery on the break? Then no doggie bag and no cash to pick up something later. Get on or get off but don't complain about what your getting, or missing out on.