Tracy, IMHO it remains a pretty tough proposition!
At first sight, charter a 40-45 ft vessel for 6 months in order to get a better taste of the cruising life style sounds like a reasonable idea. So, why not simply go back to Sunsail and charter one of their vessels for that length of time? I am sure you have already considered and rejected that approach, since: (a) the cost would be horrendous (yes, they should give you a discount but with an assumed 50 % occupancy rate they have little incentive to give you a bigger discount than that); (b) they still would not just let you cruise anywhere you wanted to go (not even with a captained charter) and might, in fact, not even let you sail at night (all because of their insurance); and (c) it is doubtful they could find you a steel boat (why do you want one anyhow? see my postscriptum)OK, so you are looking to charter from a private sailor.....Unfortunately, half the sailors on this board would probably rather rent out their SO than their beloved vessel. However, it so happens you remember the movie "Indecent Proposal" and know that he right amount of money will always do "the trick"!nSo what is the magic $$ number? Well, let's assume the bluewater ready vessel you want to charter is worth a modest US $ 150,000; all owed to the bank at 8 % interest and fully written of in 20 years. Moreover, the skipper takes real good care of his vessel (after all, it needs to remain a desirable and safe charter vessel) and spends US $ 15,000 every year on repairs, maintenance and upgrades plus pays US $ 2,000 in bluewater insurance. So, unless he or she is running a charity you will have to cough up approx. US $ 20,000 just to cover his costs. Double that to US $ 40,000 to make room for some profit and leave a buffer to replace a possibly screwed-up engine and other nightmares and you are probably getting his attention, i.e. at approx. US $ 1,500 per week. Starts sounding a lot like a Sunsail deal, right? However, in theory you now have the advantage that you can go anywhere you want and even sail at night!So, he informs his insurance that Mr. Tracy will be skippering his vessel for the next 6 months and guess what happens next? Right! You will have to find your own insurance (which will be next to impossible unless you do have a lot of experience and a qualified second person on board). Alternatively, you will need to provide a US $ 150,000 bank guarantee of sorts. Maybe, he'll settle for your house, if you happen to own one. At this point it probably becomes easier to buy your own vessel than to trade your home for someone else's boat.As you can see, it gets pretty complicated in a hurry. Nonetheless it is not impossible. However, one thing is sure: it will never be cheap or necessarily make a lot of sense.....Have fun!Flying DutchmanPS (true story)Hanging over the seawall in a little Dutch fishing harbor I once met an old sailor who slowly sucked on his long-stemmed pipe and remarked: "I remember the times that boats were made of wood and men were made of steel. Now boats are made of steel, and ....". He did not finish his sentence but threw a long and disapproving glance at "Rivendel I", our Pacemaker houseboat, neatly tied up to that same seawall. I did not have the heart to ask him if he had ever heard of fiberglass..... HM