Excellent points have already been made.
First, if trawlers (or any vessel) is going up or down a coast, the most common failure, is that sediment is stirred up from the fuel tank, and filters plugged up.  On our last trip from the PNW to the Los Angeles Area, we came across 3 boats where they had used up their fuel filters in rough seas, and then run down the batteries trying to re-start the engines, to keep going....
So before going offshore, or even a coastal trip POLISH YOUR FUEL/clean your fuel tanks!  Carry plenty of fuel filters, along with the other spares (water pump impellers, a water puppy to use as a back up, perhaps a small gas powered generator to use to charge batteries, if the diesel engines fail.)

Second, if you have any question about bits and towing cleats, bridle the boat.  This means that you pass a hawser (at least 1" line) all around the boat to be towed, and then use small lines to hold it in place, from cleats.  On our own boats, we always had very strong forward bits/windlass.  For example for the Cal 46, we had a 1/2" aluminum plate cut and drilled for all of the forward deck cleats, and the windlass.  This was epoxied in place under the deck, to spread the load out over a large area.  On the 62 foot motor sailor we took Calif. to Europe and back; the Sampson posts were 3 x 6 timbers, which were thru bolted thru the 8" x 8" base of the bow sprit.  The butt ends of these 3 x 6" timbers were glassed into the hull way down in the forward part of the anchor locker.  We had two Windlasses--both of these were tied into a 1/2" aluminum plate, which was then tied into the Bow Sprit, the deck and the forward cleats.  The aft cleats on both boats were backed with 1/2" aluminum plates, about a foot square, epoxied into the underside of the deck.  Also both boats had manual winches (as sailboats do--but power boats should also have), which were strongly backed.

The admonition to keep people away from the tow line, is so important.  We were towing a 36 footer, in only moderate seas, at a speed of 4.5 to 5 knots.  The boat was about 200 feet back, and the length of the tow was spaced to be in sync with the waves.  I had just warned the crew to stay off the aft deck--and below.  About that time, the boat we were towing's bow cleat pulled out of the deck.  It landed in the water, just off the beam of our boat!  (line still attached).  We stopped and bridled the boat we were towing at that point.  Lesson learned!  Don't trust other people's estimate of the strength of their mooring gear.

Even with the bridle Rick described, I have often had trouble as I started a tow, because of the torque of a single prop, which would pull the towing vessel to one side.  In that case, go very slowly, and re position the towing vessel, until you get way on the boat being towed--plus have someone on the wheel of the boat being towed if possible.

As for those who say "get a Towing Service".  The vast majority of the waters of the world do not have any towing service!  Be prepared for your boat, and other boats if necessary.  If you don't have experience, then study about towing techniques, and safety proceedures.

Bob Austin

Another towing note. I tow with the dinghy by making a long loop with a
bowline and place it over the outboard, making sure I don't crimp fuel
lines and cables. There really isn't any good way to attach a line to a
dinghy that permits you to steer.

Jeff on Adirondack
in Portsmouth, VA for the summer