Any help/tips on shipping a vehicle from Kentucky to Alaska?

Take pictures of EVERYTHING. If any damage happens en route, it will be your word against theirs, and they will likely win. As far as having your vehicle winterized, make sure that it has the proper oil, coolent, as high a CCV battery as you can get, and good all season tires (and probably snow tires as well). If it is an older vehicle, I would get it checked out to make sure it would even hold up to the winters there, they can be very harsh. If it isn't 4 wheel drive, I would almost look at options other than shipping, but that would depend on where you were at financially.

Add a four receptal electrical junction box under hood in engine compartment.. Then add a headbolt heater and trickle battery charger. You can plug these in during the day and at night if you do not have garage. Also you will have extra place to plug in heater for can.

Unless you can ship it ahead of time, usually Transportation tries To get your flight lined up to leave a few hours after you drop off, from the VPC location. Keep your reciept for the cab/uber to get from the VPC to the airport.