"Move the boat out?"
Rob, I'm not sure what you mean by "move the boat out." Do you mean you can't make the NYC to Block trip during your vacation period, and are thinking about pre-staging the boat closer to Block, and driving to it at the start of the vacation cruise?Two years ago I sailed down the Sound from Westport, MA, to Block, then Stonnington, Mystic, Old Lyme, Milford, and Larchmont; then headed home via Port Jeff, Mattituck, Block then Westport.The homeward legs were solid day sails. Port Jeff is O.K., but not particularly hospitable to sailboats and dinghies; though we did anchor (for free) on the left side as you enter the harbor. Stay clear of the big mooring ball which is used to park coal skows, sometimes two in tandem, as coal is delivered to the powerplant there. The North Shore of L.I. is pretty desolate. For places to visit and eat, etc., stick to the Connecticut coast. Milford was great, as there is a fun outdoor bar within walking distance. We rented a slip in Milford.If you're staging the boat, I wouldn't go too far up the Sound, as you could miss some nice sports. Note that when the Sound is ebbing you get a significant boost. I made the 50 or so miles from Mattituck to Block with just 35 miles measured under the boat on the knot log. The current at the Race peaked at about 6 knots that day, and I hit it just right. Be prepared for fog, and for wind. In August we sailed in heavy fog many days, and enjoyed SW winds at 25 to 30 on that Matt. to Block leg.