Educating and influencing the yacht owner?

Not an expert, or even a working captain, but I would say, "his boat, his dime, his rules". Certainly state your case and try to sway him but if it don't work you either want to continue running the boat or you don't. He'll have no trouble finding a captain that will do it.

Explain to him the trip, length, and duration and then the decision is his.

BUT, definately explain to him that you can try to leave on that date, BUT there is no guarantee due to weather and you will need to pick a weather window in order to do so. Also tell him that you need to take additional crew to stand watches and bring your father and the blonde along. There is no way 2 people can safely stand watches on an 8-10 day voyage 24 hours a day. The Coast Guard CFR has rules in there in regards to how many hours a day, and how many crew you need to stand watches on a 24hr+ voyage.

A good weather routing service is worth its weight in gold. And tell the owner there are no set dates.
That time of year I would head out to Bermuda and wait there for the weather guy to say go!
About 10 days to the Azores, then another 10 or so days to the Med.
I did a transat this way in September of 1990, we ended up getting routed around the south side of Hurricane Isadore, Herb from Southbound II did a great job of keeping us out of the worst of it, but close enough to get an incredible ride.

Well said.

If it is the sense of adventure that keeps the boss happy and the money flowing, welcome him along for the trip. That being said, he has to understand that there cannot be a schedule.
After making the crossing, he will either decide that he'll never do it again or that it was the best trip of his life and you will become invaluable to him.

Hi,

How fast is this 80 footer and how fast/far can it motor?

Don't be lulled into a false sense of security.

I did a crossing in Sept 2002 from Viareggio to FLL on a 52m Motor Yacht, the plan was Viareggio to Azores , refuel and cary on to FLL. There were so many TRS's coming up from the South that we left and went south passing close to the Canaries then stopping in SJU for fuel on the way, it was the rolliest most uncomfortable crossing I have ever done.

I used to deliver cats nearly half your boat's size from France to Maryland. 6 a year. There were no weather windows, only schedules to meet.

Doing a transat with a total of 2 crew is extremely uncomfortable and can only be done reasonably safe when you know the route and know and trust your mate IMO.
A transat with a total of 2 on a 70 footer is plain insane. No one is still sharp after the 3rd hour in a night watch and 3 times 3 hours of sleep is worse than one stretch of 7 hours straight.
The atlantic is crowded at places and you'll need to have a contingency plan when it comes to watch crew in bad weather.

As an owner and sailor, and one who has made the crossing, specifically in a sail boat, I'll echo what Capt J and Ken said. Both of whom have far more experience than I.

You the boss and two friends sounds like the recipe for a disaster to me. Unless the boss understands you are the boss while underway and the friends have at least some real bluewater sailing experience.

I had a friend do a crossing like that where they had to lock one “crew” member in the head after he lost it during a multi day storm.

Ditto. Check the quals of each person coming. This is no place for tourists who will be bored when they're not scared, and end up expecting you to cover all shifts and serve drinks and meals. I'd also have the blond waiting for me when I land unless she is a competant sailor.
I also get the feeling that your gut is nagging you about this. Listen to it. That's probably your experience trying to get your attention. That the owner wants to cast off at "1000" on a specific date 3 months away is a red flag to me that he may be thinking of this like a lunch cruise. Some jobs are smart to pass on.
If you do take the job, hook up with a good weather service.

The short trip to Bermuda will give the owner to change his mind before you make the long jump.
A trip like this I would take 3 experienced sailors as watch captains and run a 3 on 6 off watch schedule. 3 others with less experience to be watchmates.

If you believe it wise to make the crossing with your dad and a "cute blond" I question your professionalism. Your grammatical skills in the first post only serve to bolster that impression. Even thinking of bringing the owner who you admit could be a liability on such a trip seals the first two thoughts. I could be wrong, but I'm getting older not bolder.

Not sure about all that. My feeling is that the OP is not a captain, or at least not one with experience in this type of trip. There should be one on this voyage. As to "charts that show hurricane activity", start by Googling maps, not charts. This will get you started: http://www.csc.noaa.gov/hurricanes/#
But unless you're some sort of master handicaper this historical info will help you very little for predicting future storms. That's a day to day job starting when they come off land in Africa, and examining every subtle pressure system, steering winds, sea surface temps, etc., etc. But even the computer programs seldom seem to get it right more than a couple of days out. Set a planned departure date, and a couple of weeks ahead start looking for weather windows, with the help of a weather forecasting service.

That is a very rash judgment. My Dad probably has more sea time in reverse-gear than most boaters have in forward motion, and my cute brunette is a pretty competent watch-keeper too. I would cross the Atlantic with them any time.

I can confirm Ken has a cute brunette.

I'd give up my PFD for a cute blond on a trip like that, but she'd still have to be a competant sailor.

While I can't comment on your watch-keeper (I'll trust Carl's word.... err... eyes....), I am going to steal that line just prior!!!!

I'A BE CAREFULL WHAT I SAID ABOUT WOMEN SAILERS i know one that might take offence she is a pilot that takes your boat through wrangell narrows and she is quite attractve also i have had some very nice girls that could stand watch in some very farish conditions

on the move travler

...who has made more Atlantic crossings than Ken has.