looked in to the big shops like Sunsail...and went with a small Chesapeake charter for almost two years...worst decision in my life...
The hype is, the charter will pay for the boat payment...it might...but won't come close to paying the required commercial insurance, slippage at a much higher rate than you would get (they want the boat 3 steps from the office and pointed out to the cruising grounds) and 10-15 times the required maintenance - monthly, if not sooner, oil changes (and you can't do it, so it is at $$ shop rates), repair and replacement of required charter gear, cleaning, etc, etc, etc...and I do mean etc...then there is the whole accounting/tax/IRS thing, that costs extra every year and sometimes quarterly..
We had two charters in a row "loose the boats mooring lines" to the tune of $250-300 EACH time...they would not charge the forgetful charterers for the loss, as they did not want to "discourage one of the best charterers for next year". For every charter I could count on at least $100-125 in "lost" gear, plates, linens, lines, etc.
Then there is the boat...within the first year, the interior was trashed. One week someone "threw" vodka all over the bulkhead teak veneer and did not even touch it...I went down just to look at "my" boat...and saw the finish was trashed as were all the floorboards, cockpit and step overs to the cockpit.
If you don't mind getting a "10 year old" boat back after 2 or 3 years, then the program might be to your liking...for me
Not a chance, ever again...