I have been looking at wake photos, and trying to figure out how far back that second wave is. Maybe I need to be out on the boat to see it but from here I have not figured it out. Roughly, how far back are we talking, 2 boat lengths or so? or more? I remember seeing the sailboats with the dingy out a l o n g w a y s. How far back are we talking there?
Towing the dingy will be new to us. Probably prefer having it up top.
Harvey... When you're on board and under way the first, second, and third stern waves will be quite evident... With someone else at the helm or on autopilot just go back and, with a turn around a stern cleat or bit pay her out slowly to the top of the second wave and then just maybe a wee bit back... With your hand on the towing painter and 'milking' up just a bit you'll feel the reduced drag as you let her slightly back of the second wave crest... (The 'sweet spot' the other gent mentioned.
How far back depends on your type of boat and speed... Displacement (sailing boats you mention) often have a larger wave system with greater period... 1.34 times the square root of the waterline length along the hull.) Also, when running downwind in heavy stuff under sail you run a significant risk of the dinghy shooting aboard or into the stern if it's on the top of the first (and perhaps cresting) wave astern! Remember that the displacement sailboat (depending on size and length) will only be making 4 to 8 ± knots and the cresting wave/swell will usually be overtaking you...
Your question also reminds me that once you've payed out the proper length at a given towing speed AND THEN, after a bit or to meet or surf a swell, you CHANGE speed, ALWAYS look back and observe the dinghy or skiff. The stern wave system period will change when you change speed. (Again, type of craft will dictate how much...). If you've been towing comfortably downwind at, say 8 to 10 knots and you make a significant speed change you may well look back and find the skiff surfing down the swell and ready to bury its bow and/or riding way on the back of the back of same and serving as a sea anchor/drag. This will cost miles per gallon but you may well WANT it to create significant drag to help you deal with a difficult seas situation....
I generally use a 3/8" or 7/16" NYLON tow line (Not poly or dacron) because you want the STRETCH of the nylon to ameliorate any sudden yank on the towing cleat or bit and/or the skiff's towing eye, ring, u-bolt, etc. My tow lines for skiffs/dinghys, etc. are all between 70 and 100 feet minimum (although I'm usually not using it all).
Hope this helps.... Capn. Wes