I pack similar.
Have some frozen "extras"(Sausage or pork tenderloin for us) to fill cooler as much as possible. The pork tenderloin or link sausage can be cooked on the grill after evening meal is done. I use the tenderloin for next day sandwiches for lunch. Also, sausage goes in zip lock bag for breakfast next morning or 2.
Up to 5 pounds of dry ice is legal for carry on. But I have gone 24 plus hours with Polar Bear cooler without dry ice and all still frozen solid upon arrival at boat.

Customs not issue. Declare and state a value and they may tax you $10 or so. And often hear "buy here and support economy" . The reason we take it down is to be certain of good quality meats(frequently grocery stores are out of some items) , but more importantly we can prep food before going, making it easier on Galley Winchs. Also less chance of blood drip into freezer since vac pac'd, and allows for quick thaw in bucket of water when time slips up on you.