In my experience, not a "challenge", but just plain impossible I once tried to tow a trolley (floating tyres and a very light construction) a short distance to a sailing club on an island with no bridge connection. It became quite quickly clear it was not working... the load on the transom kept the boat from going upwind at all (It would actually point up to 45° to the wind, but move sideways).tacking and turning might be a bit of a challenge.
No, just through them the painter and towed them in their boat.Did you tow their craft and carry them as passengers?
I towed a pair of adults who'd stalled in a small (12') outboard boat. Progress to windward was almost undetectable.
That said, I recall the "Windward Passage" passed a fellow racing yacht while towing a skier!
I have towed 25 foot sailboats and a young adult in an inner tube while rowing (not paddling) one of my Grumman canoes. The 25 foot sailboat was MUCH easier to tow!my 1st-hand experience is with having a squirmy kid in an inner tube tied behind a canoe floating down a river, and I can say with strong conviction that it creates a TON of drag. but if you're thinking of towing a kayak or paddleboard, and don't have squirmy kids legs dangling in the water creating drag, then it might be ok.
tacking and turning might be a bit of a challenge.