tripwreck Share definition Flag A cruise or seaside vacation that is ruined by a hurricane, tsunami, or just wicked-stormy seas. When Hurricane Rick came ashore at Cabo San Lucas their four-star resort vacation became a tripwreck. tripwreck by BuzzKill54 October 19, 2009 0 0 Get merch Get the tripwreck mug. Buy Now — $32.95 See more merch