Chef...my comments in red below.
Fri evening- 4 hour sail rondevous in Whorton Creek- a favorite of our group already
Sat evening - Reedy Island quiet anchorage 5 mi south of the east end of the C&D Canal Deleware side
Sunday evening- Utschs Marina, Cape May after a long "lovely motor" down the Delaware Bay
Monday evening- Manesquan anchorage...is this possible from Cape May
Suggest Atlantic City is a more realistic target.
Tuesday evening- Liberty Marina next to the Statue of Liberty preparing for the Hells Gate adventure the next AM
Wednesday- up the East River to an anchorage( Conneticut or Long Island) (suggestions needed). I know a lot depends on the time of the tide up the East River, but how far up the sound could we get if we traversed that by 11 AM
With a morning passage out of Hell Gate, you should be able to make Oyster Bay or Northport (preferred) Harbor...Failing that there are nice marinas in Manhasset Bay.http://manhassetbaymarina.com/...Seymours moorings in Northport are reasonable and the launch service puts you right in the quaint down town area which the ladies will enjoy.
Thursday evening- marina in Conneticut (suggestions?)
Suggest staying on the LI side and heading to Greenport around Orient point. Nice town, several marinas, and a good jump off point for Mystic. If weather proves a problem...Port Jefferson is a shorter run alternative.
Friday evening- Mystic (is this possible) (Marina suggestion in Mystic?) Whats the total distnace from City Island to Mystic. (180 nm?)
180 miles is about right...that is 3 60 NM days or 10 hour days at 6 knots if you are really pushing. I think the trip is ambitious for the time you are allowing if you want to stop each day and not do overnighters. If you have more time than indicated...it should be great. I am not that familiar with the Connecticut side of the sound and marinas there except in Mystic proper where the Brewer Yacht yard is first class: http://www.byy.com/mystic/index.cfm