For many yrs, we towed a Cape Dory 10 behind my dad's Bristol 40 from the Long Island Sound up to Maine. Never had a problem with it. We even stupidly towed it to Bermuda. What were we thinking? It only turtled once in the gulf stream.
Never had a problem coastal cruising with the dink behind us.
Wow! You've got us beat. We've towed dinghys up and down the east coast and through the Bahamas, twice. Now we tow one from Maine to Cape Cod regularly, I don't worry about doing it. Coastal sailing, we don't see the weather surprises we might off shore for several days. Still, some dinghys are better at this than others. We've always liked prams for towing and big loads, and have a 9'6" Nutshell that we row and sail. It's been a great boat for tending a family of four. It'll fit on our 38'er, somehow, but I've never done it.
The only problem I've had with prams is a following sea where you either lengthen the painter or add more. There's ideas to add a drogue but we've never had that severe a problem, the added length of painter keeps the distance and provides the drag. Prams are like corks at sea and rarely even ship a cup of water in a big sea. (In a few deluges, I've had to stop a few times over the years and bail them)
We owned a CD10 sailing dinghy as well and loved that boat for sailing and rowing but never used it as a dinghy. I didn't think it would tow as well(I was wrong!), and sold it years ago.
