Watching people, especially couples, attempting to sail to the hook, to sail off the hook, or to pick up a mooring is the classic 1600 "happy-hour" entertainment of sailors on cruising yachts. If the wind is much over 10 kt, then it really gets interesting. A few years ago with some friends aboard our Bavaria 38, my wife and I sailed to the hook in a place known as "Hurricane Gulch", which is an area of LA Harbor off San Pedro where the afternoon summer sea breeze pipes into the low 20s frequently. Sailing into the designated anchorage at Cabrillo Beach requires a beat into that sea breeze, tacking a few times across the marked channel, to finally make the anchorage boundary, whereupon one can anchor in 9 - 20', depending on how close to the beach one wishes to be.
Here's how. As you near the spot, on your final tack (main sail only now), where you wish to anchor, you put the boat head-to-wind (and keep it there). With the boat nearly stopped, deploy the hook, and at virtually the same time you (or someone) blow(s) the main sheet, and lets the main sail luff. THIS IS THE CRITICAL STEP!! If you fail to free the main sheet the boat will start sailing as soon as the head falls off enough for the wind to power the sail. As the boat does fall off the wind, pay out your rode. As the anchor catches and pulls the bow back into the wind, drop the mail sail. Then, make yourself a drink.
Evidently, someone also beating up the channel to the anchorage saw us do this and was going to do likewise. They lowered the jib, sailed to the spot, put the boat head-to-wind, and dropped the hook. However, they did not blow the main sheet to luff the sail. It was blowing between 15 and 20 kt, so the boat took off sailing on the main with the hook down. Of course, we're watching all of this while tipping G&T's. The boat quickly gets to the end of its anchor rode, which then pulls the bow around and the main sail jibes. Now the boat is sailing down wind on the main sail in > 15 kt, somehow pulling its anchor behind it. As it passes by one of the channel markers the anchor evidently fouls the cable because the boat suddenly lurched to a stop. It was evident from our position that the rode had also fouled on the rudder. They eventually got the main sail down and after several breath-hold dives under the stern they still could not free the anchor rode. They eventually cut it free and motored away.
So, sometimes, it's not so easy as it might appear at first glance!!!