Assuming a north wind in mid-September, the tide charts tell me I have a three day window to sail from Chincoteague to Wachapreague Inlet on the way down the sea side of the eastern shore.
The plan would be to launch out of Chincoteague's Harbor of Refuge midday and sail the short distance to Tom's Cove, the same place where Washington "Tut" Tuttle anchored for the night.
Low tides for Chincoteague Inlet for three days in mid-September are between first light and just after 8:00 a.m. We could catch the last of the outgoing tide to get on the ocean and sail south the 25 miles or so off the barrier islands of the eastern shore. With a decent wind it should be easy to catch the last of the flood tide at Wachapreague Inlet.
That is if we have a north wind. If not, we'll be sailing north from Cape Charles.