Okay, Westbrook to Newport is a long day's sail, so you should take advantage of the ebb tide as much as possible. You understand The Race, and I would advise obtaining a current
copy of Eldridge and consulting the tide diagram for Long Island Sound
- then choosing your start time so as to maximize the tide current out of the Sound. As someone mentioned earlier, you don't need to worry about slack tide at The Race. I would maximize my timing so as to be as far east of The Race as possible when the tide changed.
Also consult your charts
. There is a long sand bar in front of the Connecticut River entrance at Old Saybrook. It is buoyed but use caution if your draft
is of concern.
There is also, to my remembrance, a shoaling north of Fischers Island when approaching the Mystic Area. Check your charts
for that - I almost found it the hard way on a passage into Stonington!
Once east of Stonington/Watch Hill, there is nothing remarkable. Stonington would probably be your best weather
bail-out if you needed it, with Pt. Judith next. We found Pt. Judith to be a bit shallow (we draw 6 feet), but navigable by staying closer to the greens than the reds on the way in.