A grumpy old sailor wants only to finish building his boat so he can set out to sea. But from local officals to troubled fosters kid, the world keeps intervening to test his determination to make something of his golden years.

Robert asks Jenny, a girl he found on Craigslist, to be his new roommate. Now after a year of living together, he finds himself falling in love with her, but his ability to keep afloat in San Francisco is coming to an end. With a lame job and not enough income, he has no choice but to move back with his parents in Rochester, NY. With only three days until his flight home, Robert struggles to tell Jenny his true feelings and to determine what direction his life is headed.