Pandy Girl,
I don't think the trip would be too much for you, particularly since it appears there may be a group forming-up, but you might consider:
1) If you haven't done much boating (or even if you have, for that matter), take a USCG/Aux or Power Squadron Basic Boater Course and maybe a coastal navigation course if you can squeeze it in.
2) Do some "towing ground school" with your rig. Take it to a large (empty) shopping mall early Sunday morning before they open, and practice towing/backing into empty parking spaces. The confidence you'll gain will be invaluable when you're really road ready. (Hint: if you can "practice" with an empty boat trailer it's easier.)
3) While the boat is parked in the driveway (or wherever) think and study where you want to store the necessary items you'll want to take on a multi-day or multi-week trip. C-Dory's are GREAT boats, but small, and having what you need thoughtfully stored will come in Real handy.
4) Take some day-training-trips. Your purpose isn't really to see stuff...it's for you and your crew to become comfortable with their respective responsibilities (launching, docking, knots, underway, retrieval, etc.). Find a quiet place with plenty of maneuvering room at the marina and practice both port and starboard docking.
5) When YOU feel you're ready, take off for an overnight aboard Pandy Girl. With your new found skills and comfort level you will find that being onboard for an overnight really opens up new ideas and opportunities. You may be the Captain, but discuss ALL new items with the Admiral beforehand. I've found the Admiral often has some Very good organizational ideas. Only a fool fails to listen to the Admiral.
6) I recommend the first overnight or two be done tied securely in a marina. Become familiar with the mysteries of the PortaPoddy, Wallas or Origo stove, shore power, sleeping in a berth, electricity discipline (you're on batteries remember?), how to arrange your deck chairs, mixing a scotch while onboard a the end of the day ... oops, I got diverted. When you're comfortable - go out for a few days and hone your boat camping technique. Practice anchoring in various locations. Have lunch at anchor - and watch to see if you're dragging anchor (drifting). Now try sleeping overnight at anchor ... hee, hee, hee. (Don't feel bad if sleep is a little elusive the first night or two.) By all means DISCUSS IDEAS and find new (sometimes inventive) ways to adapt boatcamping to YOUR lifestyle.
7) Whilst doing all this keep careful track of your fuel consumption and mileage. You'll gain useful insights regarding navigation, fuel burn, and performance information. Aim at getting a real understanding of what kind of range you have (or don't have...) under varying conditions and loads. Armed with this information you can make useful judgements regarding how much (if any) extra fuel you must carry for a given trip or cruise. (Remember: Scotch goes in the yellow jerry cans, and wine goes in the blue jerry cans, and if you have room for it gasoline goes in the red cans.) Determine priorities.
8) While doing all this, enjoy endless hours of discussion of the finer points of how you want to manage/adapt Pandy Girl for your particular type of boating. Things like galley and food storage, the kind of reading light for EACH berth, what kind of glasses to have onboard (answer: Acrylic or Tervis), what items to put on your various pre-departure checklists, what boating guidebooks to purchase, Navigations chips, necessary boat jewelry to buy (hint: we've found an XM radio and some small cheap Radio Shack speakers is (are?) great), proper cooler and ice "management" ...Lordy, the list goes on and on!
Goodness, this email has grown longer than I intended, and you have your work cut out(!) but it WILL BE FUN! You certainly have time to do your own "boat school" before Bahama's, but you may have to apply yourself. You'll never have a more-fun (work) assignment!
Now get out there and DO it!
C-BRAT's: What have I forgotten?
Casey
C-Dory Naknek