I just have experience with towing behind a sailboat. We were following the advice someone gave us about 1 wavelength back and it was going fine. Admittedly, we were going from Portland
ME to Woods Hole on the outside, so really should've collapsed the dinghy
(high-pressure floor Zodiac)... But the weather
was supposed to be good and we had ridden similar winds in the past with the dinghy
no problem. Yes, it slows you down, but we didn't want to worry about blowing it back up only a day or two later.
Before we got to Cape Cod
, of course in the middle of the night, the weather turned and we ended up in some confused waves. The dinghy was bridled to the aft cleats
on two attachment points. It flipped and started diving
with every wave. With my other half now on deck
we managed to pull it to the transom using winches and a spare line to lessen the load, he flipped it the right side up, and, after arguing who should do it, I jumped in the dinghy and retrieved the gas tank that had been tied to the dignhy and was now being trawled behind. After I got back on board we pulled the dinghy as close in as possible with its nose sitting on our transom. It worked well for the rest of the passage
My other half still says that if we had the engine
on it, it might not have flipped as it would have been heavier and more stable. I disagree.
It was our laziness and faith in weather forecast
that allowed us to make this mistake. Though now it's a lesson well learned: never-ever tow the dinghy unless it's in settled weather over short distances.