I had no problems bringing on my Palio cutter, which I though I might. I did get an agent wondering about my litter-a-dor, but when I said it was a cigar caddy he just smiled and said have a good time. I didn't bother trying to bring a lighter I figured they're easy enough to find.

Chris
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Last time I flew I brought the cigars in herfadors in my carry-on and had a cheap cutter, and two cheap jet lighters in my checked luggage, empty. I bought a can of butane when I got to my destination. If they search your luggage they might find the lighter and they might confiscate it, but I took the chance and didn't have a problem on either end of my trip. If you go with a cheap lighter you won't miss it if they take it. I didn't want to have to find a lighter at my destination and I didn't want to have to resort to a soft flame on the balcony of a cruise ship.

EDIT: The TSA regulations on lighters seem to change constantly, so agents may not even know what the rules are from day to day. This could result in them allowing items they shouldn't or seizing items that are allowed. It all depends on the individual agent and how informed they are of policy, which oftentimes is not very.
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I normally put cigars into my checked luggage - I have a very small carry-on. I usually make sure that they're in a well constructed box, and then make sure that they're well padded with clothing on all sides. So far, no issues.
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You shouldn't have such worries on a train, and trains run from Manhattan to Jamaica all day. :-)
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I carried 2 boxes back with me in my carry-on from my honeymoon in the DR without issue.
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I have carried on a box a few times. Usually smaller though...
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Cigars in carry on, jet lite and cutter in checked many times, no issues.
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Just don't light them first.
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