In this article I argue that the Hawaiian conceptual, cultural, and physical space called po'ina nalu (surf zone) was a borderland (or boarder-land) where colonial hegemony was less effectual and Hawaiian resistance continuous. Through the history of Hawaiian surfing clubs, specifically the Hui Nalu and the Waikīkī beachboys, Hawaiian male surfers both subverted colonial discourses—discourses that represented most Hawaiian men as passive, unmanly, and nearly invisible—and confronted political haole (white) elites who overthrew Hawai'i's Native government in the late 1800s. My ultimate conclusion is that the ocean surf was a place where Hawaiian men negotiated masculine identities and successfully resisted colonialism.