Go big
My system may seem a bit like overkill, but I have spent as much as eighteen months in a row away from any docks, and in areas of big wind and currents, so it has helped me sleep very well. My primary anchor is a Bruce 33 (although I went for years with a 22 that also did the trick). My back-up is a CQR 35. I have two Danforths for stern hooks, and a Fortress FX-37 as a storm anchor. I feel strongly that for serious anchoring, where you will swing with the wind or current, a Bruce, CQR or Delta are the only choices, as they re-set without problem. The Danforth type has more holding power in a straight line so is good for Bahamian moor or bow and stern but can be treacherous in a swinging situation.My primary rode is 220 feet of 1/4 inch Hi-Tensile chain, with 300 feet of line behind it. Other rodes use up to 60 feet of 5/16 chain and 100 to 300 feet of line. I use the bow roller that is specifically designed for the Bruce 22, It is a Windline BRM-4, commonly available. By taking the upper roller off of its axle (but replacing the axle), it fits either the Bruce 33 or the CQR 35 very well. It is installed immediately to starboard of the headstay and parallel to centerline. The original fairleads for the docklines are moved aft so that they sit up on teak blocks inside the toerail. Their lead is above the toerail. The big anchor cleat is rotated about fifteen degrees counter-clockwise to improve its lead and to make space for the bow roller. This is all quite simple to do. The chain and anchor are quite easily raised from a sitting position, on the aft edge of the anchor locker and with feet against the pulpit legs. I rock back and forth, kind of like rowing a boat. If I run into real trouble breaking the anchor free, I can always run a line from the chain to the mast winches and give a tug. If there is a lot of wind, I put the engine in gear at very low RPM's to take up the strain. If I am in a crowded anchorage, I take my autopilot remote forward so that I can steer when the anchor is off the bottom. I routinely anchor in depths up to 55 feet, usually single-handed, and the system has worked well. It would be very nice to have a windlass, but with all that chain up forward, I am reluctant to add the weight of a windlass. Plus, I kind of like to curl up on the foredeck, and it seemed like needless expense.