Anne Wilson is singing about herself as a young girl bullied for being overweight and maybe not very attractive to get the love of her dreams. However, she knows deep inside her what her true worth is and knows she is a "dreamboat" in the making, but in the meantime she is a lonely heart. She finds herself daydreaming that she is sailing out into the sun in her sailboat coincidentally named "Dreamboat Annie" -- riding on the diamond white capped waves heading out into the warm winds to caress her-- her lover at sea (it seems). This imaginary little ship of dreams gives her comfort and strength for her to keep moving as she walks down the city sidewalk with her head in the clouds, stopping occasionally to put lipstick smiles on old theater posters still hanging on shop windows-- (sad faces painted over with magazine smiles). Her daydream carries her through the rest of the day til she returns home, hence the lyric "won't be back for a while".