The Chesapeake can certainly get choppy, especially in your area with the water being pretty shallow.
Consider installing a Tricolor light instead of an anchor light. This will give you an anchor light and running lights at the masthead. Masthead running lights can be used at night while under sail. The downside, the light will require some additional wiring.
Consider installing a Tricolor light instead of an anchor light. This will give you an anchor light and running lights at the masthead. Masthead running lights can be used at night while under sail. The downside, the light will require some additional wiring.