Retrieving your anchor after using it.

Retrieving an anchor should be as easy as deployment and setting but different skills are required.  You should not use the windlass to ‘pull’ the yacht forward.  The windlass should be capable of completing this - but why unnecessarily stress the windlass when your engine (or sails) are specifically designed to move the vessel.  It is easier if 2 people are involved in the retrieval and then the person on the bow can direct the helmsman to follow the chain so that the chain remains as close as possible to central on the bow roller (otherwise you can unnecessarily wear the bow roller itself or its cheeks).  It is possible to retrieve single-handed - but you might need to make a few trips to and from bow and helm.  When the chain is vertical - don’t aggressively rely on the windlass to break the anchor free.  A Viking anchor will set deeply, giving that second to none hold, and there is no need to test the abilities of your windlass.  Leave the rode, vertical, but under tension, and with a little patience the anchor will break free as the vessel moves up and down in chop, swell and wash.  Once the anchor is free, signal the helmsman that this is so, and then continue to retrieve.

Using a hidden anchor tripping line.

When anchoring in a busy anchorage suspicious of having hazards, debris, or too many mooring chains on the seabed, it is better to have some sort of insurance enabling you to be able to retrieve your anchor in case it gets stuck.

A hidden trip line can be a good option that is worth considering in these circumstances, especially given the problems of a conventional anchor trip line attached to a buoy.

The tripping line is usually a nylon rope connected to a buoy or to the chain is attached to the rear of the anchor on one end and attached to a buoy or the chain on the other end making it visible in case you need to use it.
In case you find out your anchor is stuck and cannot be retrieved all you need to do is grab the tripping line, release the tension of the chain, and release your anchor using the tripping line.

The "Hidden Trip Line" is a better option than the one connected to a buoy and this is how you set it up
Attach sturdy carabiners to each end of a strong floating line, preferably Dyneema (Dyneema floats and it is stronger than polypropylene). The length is determined by typical anchoring depths.
When anchoring, attach the line to the shank nearest the heel of the anchor most have a hole for this purpose.
Deploy rode (chain, of course) and attach the other end of the hidden trip line, a couple of feet ahead of its length, for example, a 30-foot trip line should be attached to the rode at 28 feet or so so it will float above the chain but far beneath the surface. It only takes a second to snag a chain-link using the carabiner as the rode goes by. it's easy to see that you're reaching near the end of the trip line length as the chain gets deployed.
the trip line is out of the way and hidden below the surface. If raising anchor and it gets stuck, it's usually the anchor getting fouled and the trip line can be easily unhooked from the rode and attached to a line and retrieve your anchor.

The Viking anchors design has a pooler groove to help you avoid the use of a tripping line.

Once the anchor is on the bow roller apply a chain hook and release the tension on the windlass.  Using the windlass to secure the anchor relies on the clutch - which might release and your complete rode hanging off the bow roller will do nothing for the yacht’s sailing ability!  Use the same chain hook as back up when we are at anchor to secure the anchor at sea.

Make sure that the bitter end of the chain is attached to a strong point in the chain locker.  If the gypsy releases that securement is the only means to stop all your rode deploying on the seabed. 

Here you can see the Puller groove in action