Open Water Swimming Highlights
- She crossed the Au'au Channel (Maui Channel) between the islands of Lanai and Maui on 23 November 2012 together with Josh Bittick, Eric Compton, Celia Compton, Jaek Horner, Cameron Lyon, Nicholas Zachmeier, Van Cornwell, Katie DeMieri, Mark Baker, and Alex Webb.
- She swam the three channels between Maui, Lanai and Molokai in Hawaii on three successive days on 12-15 September 2019 in the Au I Na Mokupuni Ekolu Endurance Challenge Invitational:
Webb appeared in Sports Illustrated's Faces in the Crowd column in its 31 December 2012 issues that read, "Skyler, a fourth-grader at Le Jardin Academy, swam the 8.8-mile Auau Channel between Lanai and Maui to unofficially become, at 10 years and two months, the youngest person to complete the crossing. She finished in 6:59:55, covering approximately 12 miles overall due to tides and currents. A member of the Aulea Swim Club, Skylar was the youngest finisher at the 2.4-mile Waikiki Roughwater Swim this fall."
- Channel Swimming With Aloha
- 2019 ʻAu I Nā Mokupuni ʻEkolu
- Swimming Harmoniously From Lanai To Maui
- Aulea Swim Team Living Up To Its Name Across Auau
- Aulea Swim Club
- The Baker's Dozen Stay Calm, Cool, Collected In Waikiki
- Open Water Swimming
- Marathon Swimming
- Sports Illustrated Faces in the Crowd
- Thrice The Fun, Triple The Challenge: ʻAu I Nā Mokupuni ʻEkolu Swim Challenge