We tend to be decent tippers when receiving personal services, like at a restaurant, haircut, etc. However, the whole idea of tipping a business owner who is giving me a bill for professional services just doesn't feel appropriate. I haven't ever tipped my self-employed diesel mechanic - should I have? I never tipped the self-employed roofer whose crew reroofed our house, either. We had a tow when we had a relatively soft grounding on the Erie Canal last year on the way down here. The operator was the owner. He billed TowBoat over $1500 for driving his trailerable boat down, launching it about 75 meters from us, then spending maybe an hour from trailer to trailer. I thought the charge, which I saw weeks later, was outrageous. I don't think any tip in this case would have been appropriate. He did a creditable job, and collected a handsome fee for it. Charter crews may be another matter altogether, if they are working for a company owner and are not the owners themselves.. I happen to think business owners ought to pay their employees appropriate wages so that they aren't dependent on gratuities, but that's just me, and we all know they don't. I've never had a charter crew, but we did do some WindJammer Barefoot cruises years ago, and it was "suggested" tipping the crew 10-15% of the charter fee. What that really is saying, basically, is that they are quoting you a fee 10-15% lower than what it really should be. Then, if you don't budget for that and don't have it to tip at the end, you fell kinda like a schmuck. I don't think it is right for an industry built around that practice, like the restaurant business, but it is. At least it does give you a sense that you have some way to express your relative satisfaction, or not, with the service. Don't get me started on cases where they add a 15-18% gratuity right on the bill! If they are going to do that, I think they should just raise their prices 15-18% and pay their staff themselves. On the otherhand, that is usually less than what we were going to tip anyway...