You will probably need two days, assuming no night sailing. I assume you have a good outboard for when the wind dies. Try to head east on the sound on an ebb tide, the current will help you, and if you have the usual southwesterly breeze, a spinnaker or a poled out genoa will also help. I would duck into Westbrook (good fair weather anchorage right behind Duck Island) or Saybrook for the night... there are no harbors on the LI shore that you will be able to use.
On day 2, just go across the sound to Orient Point. Rounding Orient is pretty straightforward as I recall, but it's been quite a few years. Make sure you have good charts, know what the current is doing and of course watch the weather. Sailing around the Shelter Island area is a treat.
On day 2, just go across the sound to Orient Point. Rounding Orient is pretty straightforward as I recall, but it's been quite a few years. Make sure you have good charts, know what the current is doing and of course watch the weather. Sailing around the Shelter Island area is a treat.