Take one advice from me. Never ever drop your anchor without a trip line, ever.
Otherwise, google 'anchor retrieval techniques'.

sirgallivant's advise is very good advise.

However I have only lost one anchor in over 35 years of cruising.

I have never employed a trip line and in 35 years it has save me endless hours of stuffing around and one $135 anchor and probably 20 meters of chain.

You have to make your own decision here.

I still don't employ a trip line and I am willing to replace my anchor if my decision is wrong.

With that in mind I usually carry three anchors.

As an afternote.

When I DID have to sacrifice my anchor it was in Sydney Harbour. I marked my anchor line with a buoy and by the time had returned about four hours later with SCUBA gear to recover it someone else had already helped themselves to it.

The world is full of opportunists.

madmission, My current boat is a little, not a lot, over your weight limits. It's the heaviest boat I have owned and I have a electric anchor winch.

On my previous boats, (3) I have only ever had a manual winch on one and that was a Compass 29.

Both my boats before the Compass were 26 footers and manually hauling the anchor in was the norm.

Electric anchor winches are worth their weight in gold. They are like autopilots, you don't know what your missing until you have one.

My anchors reasonable heavy and I do not think the last owner used it probably salied her back to the mooring most times, there is a light weight anchor on board Id say he may have used that . Ill be fitting a electric windlass Have thought of buying a manual and changing later but probably the cut out would be different so Ill wait and save up for one. Ill have all the wiring ready before hand.

We used to anchor my fishing vessel in 120 metres of water regularly. 18 tons and 12 metres of 10mm chain then anchor rode. I could raise the anchor myself but I had deckhands to do the dirty work. When it was time to go home I would attach a large [12 inch] bubble with a couple of hard plastic bubbles attached on a rope to the anchor rode with a large SS shackle. The shackle has to be large enough to slide over the chain and shackles. Mine was one I made and it was about 6 inches across. Just let the shackle slide down the rope so the bubbles float clear. Then with out shortening up, I would drive the boat around the bubbles till they appeared near the stern. Deck hand would pick up the slack rope and hook it over the stern bollard so that the bubbles just disappeared aft of the boat. At this stage I would apply full throttle and drive straight up current. The bubbles would disappear underwater and depending on how well wedged in the anchor was, sometimes going down full depth! Eventually the whole lot is streaming astern. Then stop and drift down and recover the rode, or drive down the line and have the deckhands rip it in. Stop alongside the anchor and chain which just floats there and recover that. Finish making the coffee and flash up the TV for a movie.

Amateur fishermen use a similar method just on a smaller scale. There is actually a spring loaded gismo they use to grip the rope when its raised. Obviously you need some room to carry out this evolution.

I only anchor my yacht in shallow water and use the same method as Franrick. This means I have to take the weight of the anchor and chain but its only for a brief time.

Pain on my 28 that there is no place for anything on the foredeck because of the cutter rig and two hatches.
Three anchors, 20 lb sand, 27 and 35lb mansons, 1x 30m 3/8 normal, 1x 50m close link 3/8 chains lots of nylon rode, double dose of wheatbix and a full scuba gear if all else fails.

i had to free dive down to free my chain for the first time last weekend. Thankfully it was only 5 metres and the water was nice and clear. Chain had dropped through a 4m long crevice between two rocks and under the deep lip of one. Would have been faffing around for a while trying to free that without having seen it. Anchor tip was also under a lip on the other side. I slept well the night before when I realised what I'd done (I've scuba dived the site years before and mis-remembered the position of the rocks in the bay - silly). I don't think I could free dive down and rectify anything over 5-7 metres, esp with the short fins I keep on board.

I have 8mm chain. I imagine 10mm chain is a LOT harder to haul.

So it sounds like best to break it down to separate steps
1. retrieve the slack by motoring forward carefully ,
i think it unlikely to be physically able to haul 4-5 ton of boat in anything over 10 kts
2. Take up slack and break the hold on the bottom either using the buoyancy or motor propulsion
3. Lift the tackle on board , hand over hand on a heaving foredeck
I know how difficult this can be on my 20 'er
Level of difficulty must increase with size surely there must be tricks or magic....not

So if you have a winch its just a matter of hauling in the whole shebang with the flick of a switch ...sounds like a necessity

Thanks for all your inputs ....i am thinking open anchorages and often lee shores
Down south port phillip , westernport and bass strait most weather.
Not the gippsland lakes.