I use to sail my boat from Cape Cod to Maine and leave it at various places along the way to come home, work, etc. I simply made up a special anchoring system and leave it that way. It worked fine. I had a Bruce and Danforth on chains to a swivel (20 feet for each) then 30 feet of chain from the swivel followed by 3 strand. When we have hurricane warnings here on the Chesapeake Bay, I move my boat from my mooring to my anchoring system...(anchoring systems absorbs the exaggerated rising water better than the mooring). My boat is an 1967 S&S 37 14,500 lbs. Have had the boat since 1984 and still going strong. Obviously pick a very well protected harbor for which there are many. If you can't find a place to stash your dingy, you can always carry an inflatable along.