I do similar trips as well getting to the boat and on the return trip home.

I carry my EDC on me (except when flying when it's in my checked luggage). I also pack my BoB (100% equipped) and PSK in a duffle bag or parachute bag along with the clothes that I will need. This way, I don't stick out and nobody knows what I have other than what is laid out in my room, at my destination.

My BoB, when going to northern latitudes @ this time of year also includes my Artic Gear. Being paranoid, as I am, I am prepared to walk home from wherever I am if TSHTF.

The good news is that being permanently assigned to a vessel, I can leave a Bob here onboard the boat and travel back and forth with my EDC and PSK.

I hava another BoB at home.