I know this idea isn’t popular with a number of cruisers, but I don’t think it is ever seamanlike to tow a dinghy when on a passage. For starters, the drag is considerable and a real impediment to sailing speed. There are many other reasons, of course, starting with the fact that towing a dinghy is bound to be a distraction. Then there’s the question of potential danger to the crew if the dinghy should get loose and has to be recovered.
Finally, losing one can be expensive; most insurance underwriters I know aren’t very sympathetic to the idea of making a payment to someone who lost a dinghy when it was being towed. For me it’s not that hard, and it’s a lot smarter, to make a sling or other device for the dinghy, attach the main halyard to it, and then hoist it aboard. Tie it down and forget about it until you get to the next port. H.R.