If I were in your shoes, I would consider doing something on one of the Windjammers in Maine and let someone else be repossible for all the details the first time. For details check out Maine Coast Windjammer Sailing Vacations - Maine Windjammer Association
. My wife and I have not
done this yet but are considering it. There are a number of large boats but there is actually one I believe that is limited to only 8 or 10 "passengers".
After Maine, check-out chartering on Lake Champlain. This is a great place for newcomers, lots of water, good winds in summer, refreshing water, lots of fun anchorages, and best of all no tides to worry about. A lot easier than Charleston, SC, which is where we learned and got our certifications. One of my seasoned New England sailing friends pointed out, however, that if you do run aground in a lake, you can't wait for the tide to float you off. Finding a charter boat on the lake can be difficult, but if you have trouble let me know and I can point you in the right direction.