Group Cruising Charter?

[Time2Go]

Hi Friends,

I'm busy getting my Mariner 2+2 ready for the coming season
on the lakes of western of NJ. However I can't get the cruising thing out of
my mind. So I'm thinking of towing the boat up to somewhere around Kingston, NY
and sailing down the Hudson to somewhere around the George Washington Bridge.
(summer 2014) Lots more research to be done. Any thoughts or input would be greatly appreciated.
I did Haverstraw to Lincoln Harbor years ago so am somewhat familiar with the Hudson..re: current ,barge traffic and so on.

Also, those who have listened to my plans change and morph over the last
5 months know I wanted to purchase a boat and cruise the Caribbean the winter of 2015.
Then for a variety of reasons, reason took over until I can pull off
the full time move down south. So I plan to get some certs from ASA this summer
and then do some chartering. So here's my question:

I'm thinking of trying to put together a group of 3, to charter a boat with 3 cabins
for 3 weeks. The boat would have a minimum of 3 cabins with the plan being
that each cabin cost the same regardless if it's a single or couple, with all other
expenses being shared on a person by person basis. So for example
the boat charter is 12,000.00 each cabin would be 4,000.00
All other expenses paid on a per person basis, so if provisions are
1500.00 and there are 5 people on board (2 couples & 1 single)
each contributes 300.00 as so on. The idea here is to get the real feel of
cruising while greatly reducing the per week cost of going at it alone.

Has anybody done anything like this before?
Pros and Cons? Experiences? Smart or Stupid?
I happen to think that this is better pulled off with new friends or acquaintances
then with old friends (too good a chance to turn long time friends to ghosts)

Anybody interested in something like this for next winter send me a PM
Thanx All
Neil