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Well just bought our first boat...a 31 ft Larson cruiser. The boat is in California, I am in NY. I paid for 2 months dockage so I'd have time to figure out th best way to get her home.
Being that I plan on keeping her in a Marina here in NY spring to fall and winter in FL, I was planning on buying or even renting a cheap tri-axle trailer down south and selling it when I get home to NY...I know I'll break even, maybe even make a few bucks. Now this is where the pollack in me shows...I don't have a large truck, no interest in gettng one, so I figured I can rent a Penske to haul this. Yeah I know you aren't technically supposed to, but I know several people that have done this i the past. I may end up doing well with all of this because I now have found a friend tha is movig from LA to NY and will pay ALL my gas cost to haul their stuff. The only cost so far is the cost of the rental ($740)....with the plane ticket down there I'm looking at a total cross country transport bill of under $1000 including airfare and hotel. Sure as hell beats th 5000 bid from uship...
Now my question is this, I know the Penske trucks only have a 2" ball, what is the typical ball size required for a larger boat trailer. I know tis may sound like a silly question, but I need to see if 2" would work or if it would be safe to change the tongue on the trailer to accomodate the truck. I am also trying to see what if any permit requirements there may be with this boat.
Suspect you will find that you need a 2 5/8" ball for a trailer to fit that boat. I also think you will find the ball on the Penske truck welded on so you can't change it.
Shoot, wonder what other options I might have....really don't want to pay $5k to transport to $13k boat...what size pickup would be suitable? I remember renting an Silverado a year or so that had a hitch.
Yes, you will need oversize permits for most states. You would probably be violating your rental contract so you would end up with no insurance coverage. Your auto carrier likely wouldn't cover a situation like you describe if you had an accident. Towing a rig that size 3000+ miles (in the winter I assume) with a truck not designed to do so just seems to me to be a recipe for disaster. Given that the boat on a trailer will be about 40+ feet long and you have a reasonable Penske, you're looking at 60+feet overall. Few of us have the experience to pull this off safely, even with the right equipment.
On a more positive note, I shipped numerous large oversized pieces of equipment on a low boy and flatbed trailers from Calif to Florida for about $2200, and $1650 from IL to FL. The carrier I used about a year ago was Summit Worldwide. If they can't help, they might know who can. I would suggest you shop around some more and talk with some commercial carriers for rates. I would bet that a big part of the $5000 cost quoted above was getting the boat on a commercial trailer chocked, blocked, secured and wrapped.
I was fearing I was going to need to buy a truck....looking at craigslist I found a bunch of 99-01 work trucks. Would a F-350 be sufficient? There are a few down there that can be had for under $5k. Closest to that around here would be $8k...something else to sell when I get home, probably make a few bucks on that too. Not realy sure about the whole Mexico bit, don't need my "new to me" boat being a gift to some cartel leader's kid or something. Really looking forward to getting her back home into the Morton building and doing some cosmetics...boat did very well in the survey, so now its time to make her pretty before spring.
Pay someone to haul it, you asking for problems going from CA to NY with a used trailer and a $8k, 10 year old work truck. I also would not count on making any money on those items when you decide to sell them either.
Well.....I am sure there were not any 30' Larsons on the east coast for 13,000. They were probably all up around 15 or 16. Boy did you show them! lol.
Listen, coming from experience in hauling, this is a mess waiting to happen. You will need overwidth permits in EVERY state you drive through. Your best bet is to call a permit company and yes, you are looking at about a 1000.00 worth of permits. Transit America is who I use, their number is 800-228-7577. Keep in mind you will need a triaxle and you will definetly need a diesel. Even still, plan on about 1000 at least in fuel, cost of trailer, cost of permits, cost of truck, insurance and blah blah. This is of course saying that nothing will ever break down, and yes, it will break down.
Do yourself a favor and just hire the hauler. The boat will get here in one piece.
Oh forgot one thing, 300 larson, I am guess with an arch? Better not be over 13'6" on a trailer otherwise its overheight and pilot cars are not cheap!
Just bought the boat....now to get it home :) 
