Go around if you overshoot. Expect plenty of idiots who have little idea how to skipper a boat. Never allow anyone to have hands over the side. You need to launch way way early as ramps all along the coast will be frantic. If we have had sustained southerly sea breezes there might well be a surface current south to north so you need to track a course in a southerly arc ..... 

 Swum it many times and skippered.  My tips would be:

1. Know how long it will take the swimmer to get to the 1km mark.  That way, you know when the wave is off and can time it from there. Swimmer should know within 1 min how long it will take them.  If they don't get them to time it.

2. Ensure you know if the swimmer will be on the north or south side of the course.  Alternatively, straight up the guts.

3. Make sure you know what your paddler looks like

4. If you're skippering for a team, make sure the team has a good change-over process.  We generally throw out a small fender and make sure someone is ready to pull them in.  Clear communication to ensure the swimmer is away from the prop.

Once you have your swimmer and paddler, the rest is pretty easy, until you get to rotto and the boats start to squeeze in again.  When you get to Rotto it get's hectic.  Again, if it's a team, they need to be sure they're ready to go.  You also need to figure out if you're on the north or south side when heading in, because they don't want boats cutting across all the swimmers. eg. if you're on the north side and have made arrangements to meet south side of Thomson's, you're going to have to head back out to sea a fair way to go around,  Good luck trying to find somewhere to anchor unless you're there early. Be prepared to swim into the shore.

Above is perfect and also  Stay  a bit infront or swimmer and kayak so the kayak  an see you and can follow your direct corse  if they need you just put in neutral and they can catch up easy if an emergency and needed do a turn to pick em up if you stay too close or beside them you  will end up  doing extra  distance because it's harder to hold a line 

Use a boat with twin motors, much easier to hold straight in all that wake and slop.

Have a clear protocol worked out for props in neutral/boarding especially near the

end when swimmers , skipper exhausted.

Have lots of towels, the swimmers seem to get cold easily

Good luck

 Did you attend the safety brief?

Plot your course before the day.

If southerly blowing keep to the left of the course.

Always turn motor off when swimmers want to change or board.

Plenty of dry towels for the swimmers.

I made up small flag for paddler made it easier to pick up at start of race.

Be alert.

Have a great day.

 Thanks for all the tips, some ripper considerations there, 

tom- safety brief is on the 1st- so havnt attended it yet. 

PBS- feel free to lend me a twin screw boat :), good scoop with the swimmers getting cold ( i was wondering why i have a bag full of space blankets appeared ...) 

 Give your gearbox a service before & after. It will be getting bumped in & out of gear all day long....

Other than the boat ramp, finding your swimmer/paddler is probably the worst and most stressful part.

People are travelling around and lots of boats moving in 360degs all interacting with other swimmers/paddlers. The simpler you can make finding them the better...

Remember that as skipper, its your call! I had a good friend swim the Port to Pub in a duo and I call it/cancelled after about 5kms. His lips were blue and he couldn't warm up/stop shaking. We tried everything to warm him up and let him do two more rotations. Whilst he was disappointed, he was grateful afterwards that I was pretty firm on it. The race was cancelled 20mins later as it was windy, cold, choppy and getting dangerous!

My tips, some are a repeat of above suggestions:

1.  If you can, get out into the river or somewhere else with your swimmers prior to the event to practice changeovers, and best way to get in and out of the boat.  This last part is really important - you don't want to be finding out ten minutes into the swim that they are struggling with climbing out of the water.  It's hard enough but near the end they will be fatigued.

2.  Make sure your boat is serviced, checked over and ready to go.  Most likely your swimmers have spent months training for the event; you don't want to ruin it with a broken down boat.

3.  Try and get a couple of crew to help out.  Ideal is skipper, spare paddler (can rotate during the day) and one other person (if your boat is big enough).

4.  Have warm clothes for keeping swimmers warm between intervals.  Ideal are the boat/yacht jackets which are waterproof, windproof and have a thermal lining.

5.  Plot the rhumb line marks on your GPS prior to the event.

6.  Again if you have the time, practice close quarter manouevring your boat.

7.  Strong easterlies are good for the swimmers but make it more tricky for skippers.  Because you are going so slow, the easterlies will be kicking up waves straight into your stern as you keep facing toward Rottnest; beware of being swamped.  Also depending on your boat, the easterlies can push your boat along faster than the swimmer, even in neutral.  Be prepared to move forward, peel out of the main swim channel, loop around and join back up with your swimmer/paddler.

8.  Have the paddler carry a flag on a fishing rod or short pole so you can identify them easily.

9.  Be prepared for a lot of inexperienced boaters/skippers on the water.

10.  Read the event briefing information about radio use and procedures.  If you don't have one, try and get a VHF fitted to the boat.  Be aware that handheld VHF's are limited to 5W transmit power and you may not be able to contact race control on the second half of the course.  Keep the radio on at all times, and the volume such that you can actually hear it, but don't clog up the air with unnecessary chatter.  

11.  Monitor your swimmers for signs of hypothermia.

For the people who have done it. (Especially with thirsty 6cyl carbi 2 strokes)

Did you keep the engine running the whole time or start stopping all day?

Keep calm don't stress.
work out a simple signal for when your swimmer wants to be swapped out. Work out a signal for which way your swimmer is off course. They won't always be able to just follow the boat. Have Aton of fresh drinking water then some more. Snacks as well. Whatever the swimmer likes

don't forget to drink lots of water yourself as the skipper. Yep you guessed it, snacks for the skipper and crew.

for MK406 depending on conditions yes you will sometimes be drifting along. Switch the motor off. Swimmers can get crook very quickly if they have to come up through fumes to board the boat. 

Suprisingly in the middle of the course when things and swimmers stretch out it can be quite peaceful and picturesque.

take a minute to look around and enjoy the view and take some photos. It's a long day but well worth the effort.