Go for it
Willy,I've lived and sailed in your area in the past, and had no big problems with a chartered Island Packet with about the same depth keel as my H37c. As noted above, you will hit the bottom once in a while but the boat is solid and the sand and mud in Pine Island sound and down around Fort Myers will not do any big damage. My memory is that you can sail all over Charlotte Harbor and outside in the Gulf with no problems. Pine Island sound is an area where you want to stay in the channel, with a few exceptions noted on the charts.We ran aground in the anchorage back of Cayo Costa but were able to get off with a little help from friends. It was no big deal.The 37s are easy to manage, particularly with an autopilot, and the intercoastal or outside to Maine should be a great trip.I agree with the post that says read the reviews. After 6 years ownership I have no regrets and am seriously considering taking it down the coast to Mexico for a season or two.The 37s are usually (check the survey and compare prices) a very good buy: lots of solid boat for less money than most.Good luck with you search.Sanderss/v Good News