Endless options here. Depends on how much time you have? anchorage or marinas
What your port preferences are. How much money
you want to spend.. etc.etc.
could be: City Island to Port Jefferson. Port Jeff to Old Saybrook, or Essex on the connecticut river. Connecticut River to Block Island, Block to Vinyard Haven, Marthas Vinyard and then on to Nantucket
If you want to shorten that up..you could make Old Saybrook or Essex in a long day or somewhere like Westbrook Conn. Then on to block.
Block to Martha's Vinyard is 56 miles if I recall
. Block directly to Nantucket is an option, it's an ocean sail. 70 plus miles..I believe...
It really depends on how much time you have to get there and get back, and the wind
and the weather
. You're likely to run into some fog
as well, radar
and or ais
are useful out there.
You don't want to beat into the wind
all the way to MV or Nantucket..
Block island is not the worse place in the world to wait for the right wind.