Long Island Orient Point to Block.

[DougAnnapolis]

We are sailing Long Island sound for the first time. Plan to sail from Port Jefferson to Orient Point via Plum Gut. From Orient Point, planning to sail south of Plum Island, south of Plum Gut and south of the Race to Block Island. I see no reason to sail north from Orient Point to navigate the Race. Any advice to the contrary ?
WE are sailing tartan 3700.