Having a small 28 footer with no deck space to put a nice sized dinghy I have wound up towing dinghies over long passages three times. The first one, a Sears 10 foot aluminum, flipped over while hove-to in the Atlantic on a passage from the Bahamas to New York. I felt the safest solution was to just cut it loose. We did.

The second was another Sears 10 footer I towed successfully from Florida to the Virgins via 'route 64'. It towed easily and required very little stopping to bail it out.

The third time was with a much heavier 12 foot fiberglass Tortola dinghy. It was a royal pain to tow. Had to be bailed at least once a day at sea and finally swamped just short of Bequia on a direct passage from St. John in the Virgins. (We dragged it into an anchorage in order to recover it.) We did continue to tow it for a year through the islands, Trinidad and Venezuela and the A,B, C's. Finally sold it in Aruba before heading back to the states.

Would I tow one offshore again? Nah, I'm older, wiser and less athletic now.

P.S. ... Keeping a towed dinghy from rushing the mother ship when running downwind is a problem easily solvable by rigging a small parachute drogue to automatically deploy behind the dinghy whenever the towline goes slack....as it does when the dinghy starts surfing.