1. To travel in the air or on the water in an aimless or leisurely manner. It's a beautiful day to take the schooner out and just sail around for a few hours. There were a number of birds sailing around overhead, waiting to see if we would drop any of our food.

2. To travel in a boat or plain along a route that bypasses or circumnavigates something. We'll have to sail around the massive storms in Buffalo if we want to ensure the safety of everyone on board.. We're finally sailing around Cape Horn tomorrow morning.