Almost never. I don't enjoy haggling, and don't care whether I get the "best price" from a Jamaican.

On cabs, I rarely use a charter, and when I do, I usually find that overpaying by Jamaican standards is still much less than a cab would cost me at home. Just out of my own pride, I do tell cab drivers that I know what the rate should be.

This year we forgot towels and when I bought one on the beach, the guy asked me for $20. for one and I told him I know they sell for half that in town; he asked for $15 and I gave him that. It's certainly fair to tell someone "That's only worth X to me" if that's the case.

If, when I leave, a bunch of Jamaicans feel that they had a good week because I was there, that means I feel it was a better week for me, too. When I'm spending $4000. for a week away from winter (including airfare for 2, on which US Air doesn't negotiate!), it's silly to quibble with the Jamaicans about whether my total spending will be 5% more than that, which goes directly to individual people and not to a US corporation. And it's never right to take advantage of someone who is desperate, which every year I see being done.

I have a friend who loves to haggle, and does it as entertainment. When he is done haggling and buys something at a price favorable to him, he often tips a buck or two - a good solution all around.