With kids involved, when deciding on a charter company, consider the amenities they have at the base since most of us spend the first night (and sometimes last night) on the dock. The Moorings/Sunsail have full-service resort amenities like swimming pool, multiple restaurants/bars, convenience store, dive shop etc and easy access to supermarkets and other things nearby in Roadtown.

More towards your question, last summer we (two couples and a 6 year-old) chartered a 3900 from the moorings and we would not hesitate to do it again. Whatever boat you choose, I would recommend always having someone in your crew who has some boating experience besides yourself (or at minimum someone who is mechanically inclined and who is cool under pressure). While most charter boats are designed for easy single-handed sailing during most phases of your trip, things do go wrong and when they do, it is much easier for an able crew to coordinate a response. We had compound failures during a squall and things got challenging for us even with two experienced and certified sailors.

Pick a company, pick a boat and start planning! Our vacation starts the minute we put down the deposit! You're going to have a blast!