I have four flights in this journey: Sacramento to Denver, Denver to Pittsburgh, Pittsburgh to Boston, Boston to Martha's Vineyard. Transfer times are all between 45 minutes and an hour. Believe me, I'm nervous about making it all the way there in one go.
Because of the multiple transfers, I decided I didn't want to check luggage. I have an entire week's worth of clothes and stuff in a small carryon and a backpack. I am packed tighter than a turtle's butt (and that's waterproof).