>>64238395 (OP)
If you have enough suitable ones, yea. Otherwise, the difficulties of both transporting enough supplies and delivering it efficiently and safely would cripple any real effort. Modern technologies such as mini submarines could ease the difficulties of such missions, but it would be expensive and put valuable assets in danger. Not to mention it takes time, something an island being captured may not have.
>>64238398
It wasnt tried on Guadalcanal, and it was too late for those yellow suckers anyways, they were wasting away by the time serious relief efforts were attempted and only 1/3 of the garrison survived to be evacuated.