When using multiple anchors, retrieve the anchor with the least strain on it first. Once it’s stowed aboard, you can power up the others, retrieving rode as you go.
Deeply buried anchors can be difficult to retrieve. If the anchor doesn’t break out easily, cleat the rode and power slowly ahead until the anchor is free. You can also try powering around the anchor in a circle. If wave action is significant, snub the rode when the bow is in the trough and let the next wave lift the anchor.
Stop the boat when pulling the anchor aboard to keep it from banging the hull or fouling the propeller or rudder. If the anchor is buoyed, take the buoy and trip line aboard immediately after breaking the anchor so the line doesn’t stream aft and foul the prop.
To retrieve a fouled anchor, first retrieve the buoy and haul on the trip line to back the anchor out. If the anchor doesn’t come free, you may have to dive for it.
An anchor float can also help you retrieve a fouled anchor. Attach the float to the rode using a ring, and power the boat around the anchor in a circle. The water’s force submerges the float, which travels down the rode and helps free the anchor. –Samuel S. Sanford