My delivery experience is that checking baggage is awkward and can cause you to miss connections. Accordingly I generally don't take my own knife. I do carry my own inflatable PFD/harness together with a print-out of the TSA guidance that says the cartridges are okay.
Do NOT take a bright flashlight, at least if you are sailing for me. Light discipline is important. 1 dim LED is fine for most purposes. If you can't read by that light take an iPod or such with music, audiobooks, and podcasts. It takes a long time for night vision to fully recover from light.
Have a small bag for anything you take on watch with you. That keeps your belongings together, makes prep for watch easier and faster, and avoids losing things. It isn't polite to the rest of the crew to stack stuff up in the cockpit that is in the way of the current watch-stander.
Regardless of what I say, the word of the skipper whether owner or delivery is THE WORD. Ask him or her what they expect and what their own rules are. That is most important.
For me, my go-bag includes light and heavy foulies, clothes assuming two or three days out of each item, my own towel, half-a-dozen terry rags (mostly for sweat and sponge baths), PFD, small LED flashlight, iPod, 12V charging adapter for my phone and the iPod, current reading, two pairs of gloves, some odd cooking tools, spare glasses, dopp kit, and a sleeping bag in a stuff-sack. It's easier to take stuff out than to remember to put it in.
I also have a skipper checklist I go over with clients to make sure we have the stuff I feel is appropriate to the run.
sail fast and eat well, dave
beware "cut and paste" sailors.
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