We lived on our sailboat Shadowtime for eight years in the Caribbean.
Observing other boats go through what we called anchor drill said a lot about their sailing skills.
When done properly anchoring is a simple drill … no yelling is necessary, it takes a very short period of time, and resetting the anchor is almost never required.
You always anchor with your boat going very slowly directly into the wind .. if the anchorage is unfamiliar the chart should be first communicated for what depth of water to expect.
If your boat draws say 6 feet of water you should look to anchor in 12 feet or water or less.
A cruising sailor will almost always have his primary anchor … usually a plow type, like a CQR brand, on 200 feet of chain. The heavier the anchor, we had a 35 pounder, the less likely the anchor would come loose and require resetting … we had friends with a 45 pound CQR, they referred to as their sleeping pill.
When anchoring, in 12 feet water, the rule of thumb is to have eight times the depth of water in chain deployed, in this case 96 feet of chain. The more chain you have lying flat on the bottom the less chance the anchor will break free.
The competent sailor, on the bow will ask for the depth of the water by using a hand signal … one finger pointing down … the person on the wheel reads the depth gauge and reports the depth … this is the only voice communication required when anchoring, the rest is simple hand signals.
Once the proper depth has been selected another hand signal is given to put the boat in neutral … the anchor is then dropped, the proper amount of chain is deployed, and you wait for 30 seconds or so to let the wind move the boat to where the anchor chain starts to become taut.
At this point another hand signal is given to put the boat in reverse … as the anchor chain becomes taut and straightens out … the anchorer will signal for the boat to be put in neutral … the boat slowly springing forward is an indication that the anchor is set.
If you are confident that the anchor is set, you attach the "snubber" … a snubber is 8 to 10 feet of line with a hook appropriatively sized for the size of chain that you have … usually 3/8 or one half-inch.
You lean over the bow and attach the snubber to the deployed anchor chain, putting some slack in the chain between the snubber and where you tie the snubber off to a cleat on the boat.
The snubber acts as a shock absorber … chains do not give much … and reduces the sound of the anchor chain to a minimum … you'll know quickly if the snubber falls off due to the noise of the anchor chain.
Learning how to properly set your anchor is a skill all successful cruising sailors possess … if you do it right the first time … you'll never have to do anchor drill at 2 AM.
Proper anchoring will set you apart from the rookies and help guarantee a good nights sleep on board.