More than 100 year 9 students from The Scots College have been making their way up the Illawarra coastline in single file, riding and walking back to Sydney from the school's Kangaroo Valley campus.
Decked out in helmets and fluorescent safety vests, on Monday the boys completed the third leg of their journey, cycling from Killalea to Corrimal Beach.
David Johnson, head of outdoor education for the college, said the annual trip was a way for the students to mark the end of their six months at the residential Glengarry Outdoor Education Program.
"We introduced this trip as a culminating journey. Before they used to get on a bus and drive back, whereas now we've made it a journey where they make their own way.
"We've really tailored it to become a rite of passage."
On Tuesday and Wednesday the students will trek from Corrimal to Bundeena through the Royal National Park, before catching a ferry back to Sydney.
"One of the highlights is as we go through the National Park, we come up over a rise and all of a sudden you can see Centrepoint Tower and the Sydney skyline, and they all go off when they see that," Mr Johnson said.
On returning to the school, the students will be welcomed by their peers and parents.