"One of the care packages is going to an older gentleman who is a dialysis patient. He hasn't had treatment since the hurricane hit the area," Canales' wife, Aubry, told CNN.
The private pilot's plane is small enough to land in the most remote areas.
Canales lives in Atlanta and launched his mission from Florida early Wednesday. As he makes his way around Puerto Rico, his wife shares updates on Facebook
since cell towers are still down on the island.
Word of Canales' mission has spread on social media and online aviation forums, and other pilots have joined in.
"We now have 10 private planes." Aubry told CNN. "All airplanes will be doing runs on the island (and surrounding area) for the next four to six days."
The situation is personal to the husband and father of three. He is a native of Puerto Rico.
"We have a lot of family down there. Several aunts and uncles," Aubry Canales told CNN.
This isn't the first time her husband has taken matters like this into his own hands.
"He flew down to Florida for Irma. Got four people out with his plane."
Money for this trip is coming out of the Canales' pockets.
"Round trip for just his plane is $4,500 from Atlanta to Puerto Rico."
The couple set up a GoFundMe account
to help cover fuel costs.
"If you find something that really means a lot to you," Aubry Canales said, "there is always a way to do it. There are always people really willing to help you."