My wife and I did the trip last year when we purchased our first boat in Milford, CT. We broke it up into two legs. The first leg we did earlier in the summer.
Day 1 - Bridgeport to just before the Throg's Neck Bridge, anchored in Manhasset Bay
Day 2 - Thru East river out of New York Harbor to Sandy Hook, NJ - anchored
Day 3 - Outside NJ from Sandy Hook to Barnagat Bay - anchored
We mostly motored but had some great sailing off the Jersey coast.
Day 4 - Barnagat to Cape May - took a slip for the night
Day 5 - Cape May Canal to Delaware Bay thru Delaware Canal -we could have stopped at Chesapeake City, but it was still early so we continued on to the Sassafras River (this was a long day we got in late at night and ended up tied up to a T-head until we could get our slip). We had planned to keep the boat in the Sassafras until the end of the summer.
We had mixed weather, rain 2 days, sunny the rest.
In September, after Labor Day, we moved the boat from the Sassafras to North Carolina. The Chesapeake part of the trip to Norfolk went like this:
Day 1 - Sassafras to Rock Hall (34 nm)- our usual late start, we took a slip at Rock Hall because I had intended to have our autopilot installed there, but they were not able to get to it, so we pushed on without it.
Day 2 - Rock Hall to Back Creek just below Annapolis (15 nm) - anchored.
Day 3 - From Back creek to the Solomons - we were having good weather but motoring into a head wind and we did not want to tack back and forth across the bay as we were trying to make time, not knowing exactly how long the trip would take.
Day 4 - We had planned to make Deltaville, but tropical Storm Hanna was coming up the coast and the weather started to deteriorate. We had a rough time crossing the mouth of the Potomac River, the river currents and the wind across the large fetch of the Chesapeake made for very confused water. We ended up ducking into Reedville, just the other side of the Potomac. Very hospitable place even if it is a bit out of the way. We spent 2 restful nights in a Bed and Breakfast in town, while Hanna blew over.
Day 6 - From Reedville to Fisher's Bay - around a 60 mile run.
Day 7 - from Fishers Bay to Norfolk - 47 miles.
We continued on down the ICW but this is where you wanted to stop.
These two trips to this point took us 12 days with a day layover for Tropical Storm Hanna.
cheers,