Annapolis to Newport
You don''t say what type of boat you have or weather you prefer a blue water or coastal passage...so I will give you the coastal route as blue water is pretty straightforward.
First, head from Annapolis north to C&D canal and stop there at one of the marinas. Read tide tables for Delaware Bay and pick a C&D departure time that will let you use the tide down the bay as it can be slow and messy the other way! Next stop is Cape May NJ which you can enter from the Bay if your mast is short...or go around the ocean side to the inlet which is qite safe in most any weather.
Then work your way up the Jersey coast in day hops to Atlantic City...then Manasquan Inlet...then Sandy Hook (or off Statue of Liberty in settled weather).
From there you need to head up the East River of Manhattan through Hells Gate and into Long Island sound. Time your trip VERY carefuly for low slack tide at the Battery so you carry a fair tide through Hells Gate..actually good to try to time your trip to arrive at slack water at hells gate.
Once through to Long Island Sound you can Harbor Hop the north shore of long island with numerous safe harbours, mooring fields and marinas. I would work my way out to Port Jefferson then cross over to Fischers Island for a night anchorage...then on to Newport the next day.
Off shore route saves a lot of time...one day to Norfolk...three days to Montauk/Greenport and one day to Newport...but it requires a well found boat and crew and is not as interesting. Prevailing winds are favorable ths time of year though.
Write if you have any questions. Best...GB