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I also try to get the housekeepers on the side and personally give them their tips, but I do it on the day I arrive and then a few days later. I usually give them $20 (or 200 pesos--whatever that is these days) and then more a few days later.
In New York, tipping is almost mandatory but of course, in other places, it is almost non-existent. For example, in France, the waiters are highly skilled and get paid very well. It is not a part-time job because to be a waiter, you need to learn all facets of the business. It is a profession. Some people say that is the reason French waiters are often rude. They don't work for tips--their salaries are good enough that they don't need to do so. On the other hand, when I was in Quebec a couple of years ago and had rude waiters I would laugh and joke with them and most became pleasant very quickly. I often think the rudeness is a part of their trying to live up to their reputation, but personally, I don't think most are really rude. I think of them more as 'standoffish'--if that is a word (which it probably is not!). I know that after one waiter gave us a hard time because both kids, my friend's kid and Maggie, each wanted a bowl of chocolate fondue and he said it was too much, that I told him not to worry about it and just go and get it and later I gave him a nice tip. Since we loved the restaurant, we returned a few times and he was a totally different person--friendly and funny.
My take is that most people who work at the Mexican resorts are not paid well, and even when they say that at AIs tips are covered, I still feel guilty because I know that it is really the owners and management who are raking in the big bucks. It feels good to stick it to some of them on occasion. Giving orders is alot easier than doing the actual work!
Fran in NY