Re: Chartering a long Gulf trip?
What you are looking for is one of those "one off" deals that may be very hard to structure and also very expensive.
You would want something above the 30' boat, maybe at your higher 35'. April on in Florida is low season so you may get a break on charter price, especially long term. The captain, and you would not be let out without one with your experience, and certainly not your itenerary. Best guess $2,000 to $3,000 a week for the boat and $200 a day for the captain, plus supplies for both of you. Bottom line probably a minimum of $4,000 to $5,000 a week, and the charter company would have to jump through some hoops to make certain what their insurance company would cover. Add in a number, whatever, for additional insurance and damage deposits.
Airlines and chartering in local waters would be much cheaper, and would certainly seem to be better for learning and finding out if this is for you. Being sea sick for the first 5 days would be a learning experience that you could do without.