Apparatus and methods of packing leaf tobacco preserve the integrity of tobacco, help retain freshness and moisture content of tobacco, and also help eliminate insect infestation. A method of packing tobacco includes supplying a quantity of tobacco into a plurality of open containers; closing the opening containers; inserting the closed containers within a flexible, non-porous bag having a closeable opening; closing the opening of the bag; and extracting air from the bag so as to create a sub-atmospheric pressure therein. The bag is configured to hold one or more tobacco containers, such as C48 or A48 cartons. In some embodiments the bag may be configured to hold up to six containers, such as C48 or A48 cartons.