2012 Monhegan Race (an overnight race in Maine), sailing double-handed with my then 14-year old son. Typical very light wind overnight. We are battling with another boat (from another class) in the wee hours. I decide to take a nap and curl up on the cockpit sole, leaving my son at the tiller. An hour and a half later, I wake up in the pre-dawn light, my son's face just beaming down at me (big, big grin). He says,"Dad, we are sailing now; and I passed that boat!"
Multi-thousands of dollars for the boat, more thousands of dollars for running costs. Moments like that? Priceless!