I would never presume to tell you where to go Bene505!
One thought comes to mind if you want a relaxing trip: circumnavigate Shelter Island in a leisurely fashion. It is close to home, the crowds of summer have diminished and the marina rates have gone down from their summer highs. Plenty of parks with sandy beaches to dinghy to if that is your thing. Sag Harbor and Greenport come to mind as port towns that might be fun for the wife and kids and a few harbors on Shelter Island itself. The Peconic Bays are pretty bodies of water too and there is decent fishing there and in Gardiner's Bay. This could be challenging from the perspective that there will always be some sand bank or beach you could run up on.
A slightly more challenging idea would be to sail the Atlantic down to NY Harbor. You would need at least another watch keeping 'machine' other then the DM3000 as it is over 100 nm. which you should be able to do in a 24 hour period if the wind was from the north. Few areas to duck into so night sailing is normally a must. There are Shinnecock, Fire Island and Jones Inlets which can be interesting to enter or leave on an ebb tide.
Another option, sail up to DavidPM's area and visit some of the harbors up there.
Whatever you choose, have fun.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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