Another Winslow Homer painting. He captures the lines of the boat and the sails beautifully. These curves are difficult to represent authentically and many artists don’t succeed in showing these at all well. The boat in the picture is a catboat, one of the most beautiful small sailing boats. It originated in the US and is still built in various sizes and materials.
Wikipedia says: the painting's message is positive; despite the choppy waves, the boaters look relaxed. The anchor in the bow was understood to symbolize hope. The boy holding the tiller looks forward to the horizon, a statement of optimism about his future.
The Anchor is a symbol of hope and one of the meanings of the term “hope” is an anchorage: pubs called “The Hope and Anchor” use the word with this meaning - an anchorage and the means of securing the vessel.