I've done portions of your trip twice as crew on boat delivery cruises.
1st about 10 yrs ago - 40 ft sailboat w/ full electronics - GPS, radar, autopilot - from Chesie Bay to LI Sound - crew of 3... We also had inverter that could power microwave & do food prep on the go.
Due to slow hull speed we ran Delaware Bay at night to take advantage of tides - harder than we thought as there is a lot of commercial traffic
We ran outside NJ due to mast ht so have no ICW experience.
Had no real issues except a storm we ducked into Atlantic City - to get some rest, eat, do some repairs & wait out the bad Wx.
Transient docking was pretty expensive but we found a museum across from Trump Casino that had a dock and took a donation to cover dockage o' nite - a good deal.
Altantic city to NY Harbor took us roughly 12 hrs motoring - we ran a few miles off shore (~3) to avoid any wave affects of shallow shore and have a straight route.
We ran overnight w/ rotating shifts... motoring only at night and motor-sailing during day as conditions were favorable & had the extra hands available Single handed for portion of the shift - overlap at each end to info transfer - no one left the cockpit after dark - if it would have been req'd we had jack line pre-rigged and had inflatable life vest w/ harness available. Would also require full crew available for extra hands if req'd.
Planned NY Harbor arrival at daybreak which would have put us at slack tide or better at Hells Gate going to the LI sound.
Conditions were beneficial and we arrived early which was a little intimidating in the dark but worked OK.
Make contact w/ commercial traffic and monitor their designated channel (13?) so you both know what the other is doing... they were good about informing each other of moves and appreciated knowing we were also informed.
I've taken the USPower Squadron Piloting & Adv Piloting courses which included charting plus tides & currents - I'd say you want to have some knowledge of tides & have access to tide tables if you go beyond NYC.
2nd trip - 39 ft twin diesel Tiara sport cruiser - also well equipped - gps, radar, autopilot, IPS drives (joystick) & crew of 3
We left from Staten Is then N to Troy then W on NY Canals - delivery was Seneca Lk (Finger Lakes) NY
Our travel was all daylight.
We had a major problem after hitting a LOG - roughly 1 ft dia x 20 ft long which jammed in the forward facing stbd dual props of the Volvo IPS drive... dead in the water.
Had to get towed to Haverstraw marina by SeaTow - my understanding is that TowBoat US doesn't operate on the Hudson so you will want to check if they reciprocate w/ SeaTow or you need separate coverage. Our tow bill was LARGE and would have been $0 if we were a member.
Haverstraw marina (about a half day N of NYC) is a large full service marina w/ restaurant, pool, service etc. We overnighted there awaiting haul & prop replacement. ( I have a few pics if you'd like the gory details, also have a local prop shop that can work miracles - Ive used him for my personal work after I saw what he did reworking duo-props that were turned inside-out)
Debris can be hazardous on the Hudson especially after rains / hi water and logs are barely visible in some conditions / locations (wind & waves obscure them pretty well)
NYC harbor was very busy during daylight - especially early AM rush hour w/ ferries / shutttles running in the Hudson
Hope that helps - let me know if any of that raised additional questions
We are headed for Lk Champlain in July - 2 boats both w/ gennies & fairly self sufficient - actually one is the 39 Ft Tiara other is my 34 Mainship HT - do you have any recommendations for best anchorages, marinas, restaurants or other attractions? I have another thread re: Lake Champlain Recommendations
- might be better to reply there if you have anything - that way it keeps both threads focused and avoids unnecessary drift.