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"I'm not sure of the regulations on taking an inflatable PFD (we are allowed to call them life jackets again now) on a plane - you might have to ditch and repurchase the inflation canister"
The international regulations (UN) require that they be allowed in the cabin as essential lifesaving equipment, complete with inflators. The US is a signatory to that. But, each airline can set their own policy and no one sc0olds them about that. To make things worse, the TSA banned them (violating the international treaty laws) and then more recently the TSA has again ALLOWED them. Except, any TSA airport manager or inspector has the discretion to override TSA policy and ban anything they please.
Bottom line? You have to put it in the checked luggage, not carry-on, or ship it ahead (probably as hazmat because it is compressed gas), or get to the airport real early and figure the odds are 50-50 you'll have to throw out the cylinder. Do pack an extra "aspirin tablet" or bobbin or whatever the vest uses to trip the cylinder, as well.
Crotch straps? Have you ever used your SCUBA BC to float on the surface in 2-4' waves? Try it with and without a crotch strap, one is enough. With the strap the vest can sit lower, keeping your face out of the water further. If someone has to lift you out of the water, that strap may hurt but it will also keep you in the vest. And, like a BC, you may want to try the PFD in the water to get it adjusted for best fit. Spray masks and hoods are also becoming the norm, as part of the PFD.
3M sells ScotchLite reflective tape in SOLAS grades, it has a hexagon pattern on the surface and it flexs (so it stays attached) much better than the plain stuff. Sold on the web or at higher prices in marine stores. Sticks on much better if you run a bead of Aquaseal or something similar around the edges.
Sturgeron: Great for some folks, but like all seasick meds worthless for 2/3 of the folks who try it. For me, scope is the drug that works absolutely all the time. Scopace, oral pill form, is more flexible than the patches. But like all serious seasickness meds, it should be tried in the comfort of home one weekend well before you go to sea with it. The adverse reactions can be quite significant.
Towels? Waste of time and space, get a "sport towel" aka a synthetic chamois and use that. Works great, packs small. Two sunglasses? No way, buy a "croakie" or other floating strap to use with your specs, and just take care of them. Personal first aid kit? Hell no, in the worst case if there are no aspirin and bandaids and antiseptic on the boat--buy them before you cast off. Your captain SHOULD go over the boat with you, from stem to stern, including showing you where all the emergency equipment is, so you'll be able to see what they have.
Skip the satphone, buy mom some tranqs. If you buy the SPOT, impress on her that it is NORMAL for all the gizmos to not work and if it doesn't work for a couple of days, that's normal in midocean. "No news is good news" as opposed to a distress signal.
DO put together a float plan, with the boat's name and registration, the color of the hull and deck, sail configuration, etc. and leave that with mom (or someone more objective). You can find them online and you can also call your local USCG station--any of them--and explain "I'm going from A to B and want to leave a complete float plan behind. If I'm overdue and someone needs to call SAR, what do you need?" They used to have about a ten page long set of forms to fill out, which they would gladly fax out on request. Get what you can, seal it in an envelope, mark it "Open if we still gone on (date)."
And, you might want to throw in some good paperbacks, or an MP3 player, for long watches and off-watches at sea. Enjoy the crossing!