We don't tow a dinghy at all if seas or winds are short or strong.

There are a lot of ways to get a dink and outboard on board. Most charters I have done, both exposed and sheltered came with a small dinghy and motor.

With basic knots you can lift a motor onto the boat by securing the dingy amid ship and lift it on the main halyard up and onto the boat. Its much easier to carry to the transom this way with one crew in the dink keeping it off the side of the boat, the other at the sheet winch.

You can also pull a line through the back of the boom and swing it out over the dinghy and to a sheet winch.

I also bring dinghies on board to the bow this way once the outboard is removed.

I mention this because I like to not flip my dinghy, lose an outboard or pay the .5 knot sailing price.

We will have an 11' rib, 10hp motor this trip and seas may reach 6-8 feet at 8 seconds. With a rib and motor, if wind speed is less than 20 knots, I may just tow as well.

This behavior is not the norm elsewhere where I have sailed and chartered. At home I use a rollup 9' with 6hp motor that can be lifted fairly easily.