C'mon it's only the last 40' that's hard!
While fishing for halibut in Hains AK. the charter captain had us anchored in deep water.
When it was time to leave he attached a large round fender to the anchor line with a block, threw it in the water and gave it full throttle. The anchor was up next to the fender in about 10 seconds, we circled around gathering up the line and presto.
His system relied on the large fender offering up lots of lateral resistance in the water so the line would pull more or less straight up instead of straightening out. And realize this was a high HP fish machine.
For a sailboat you would probably have to attach a small para anchor to the float or... get the Admiral to put down her rod and help.