When I bought Avalon her main anchor was a pattern plough anchor of about 25 -30lb weight, attached to some 55 metres of 5/16" chain. Although I always thought it a bit small, it generally held very well if you gave it enough scope. On this trip, though, we would be a lot more dependent on our anchors. From a Boat Jumble we bought a genuine 35lb CQR, second hand and in very good condition. And, brand new, be bought an oversize (but lightweight) Fortress FX-55. To accompany this we bought about 100 metres of 16mm nylon rope attached to 10 metres of 5/16" chain. We also still have the old anchor on board, although since buying the new ones we've never had to use it. On occasions we've lent it to other people, though, when things have got a bit rough in harbour. Incidentally, the 16mm nylon anchor warp also served as an excellent towrope on occasions, its stretch making it particularly suitable for this purpose.
We have generally been happy with our anchoring arrangements, and in particular the big Fortress is excellent, and light (if unwieldy) to handle. The only problem is the effort of pulling the anchor up by hand. We bought and fitted a secondhand manual windlass, but this doesn't seem to get on with our chain. I reckon the gypsy's the wrong size, but Sarah thinks the winch needs to be remounted over the chainhole. One day we'll find out who's right! So the windlass was mainly employed for hauling Sarah up the mast using the warping drum, at which it was very effective.
There are limits to how many anchors you can carry, but there are places where a large, traditional fisherman's anchor would be very useful. One such place was Los Cristianos in the Canaries, where anchors tended either to drag, or get stuck inextricably in rocks. Several anchors, including, our CQR, got bent there.
Please be considerate in your anchoring. Be considerate both for the locals, who may, for example, fish from the beach using nets, and also for other yachties. It is NOT considerate to lie to an enormous length of rope in a confined anchorage. It is a good idea to buoy your anchor. This will allow you to trip it if it gets fouled, and will also show other people where it is.
If I was buying a new anchor now, I would strongly consider the S-L Delta, as I have heard universally good reports about it. Chris and Carole had one on "Wild Rose", who we sailed with a good deal, and the Delta seemed more effective than a CQR of the same weight. The Delta also stows better on the bow roller.
Provided the water is reasonably clear (and warm) one of us will usually snorkel down and check the set of our anchor.
An electric windlass would be a marvellous luxury, and one day I'll treat myself. But I really don't see why they have to cost as much as a half-decent secondhand car.
An anchor for your tender is a useful thing in the Caribbean, particularly if you intend to go diving or snorkelling from the dinghy. We eventually obtained one from another boat - I forget what we bartered for it.
We bought a drogue - a sort of small, high speed sea anchor - but have had no occasion to use it as yet, so cannot comment on its effectiveness.