Think sailboat racing is only for the moneyed or the skilled? Not according to Ondeck Sailing, an Antigua-based company that draws beginners into the sport by adding them to a pro racing team. Ondeck enters every regatta during the winter racing season (a lineup of three- to six-day events from early January to late April) and sells individual spots on its boat to people of all levels. The expert crew is patient with novices, and the ad hoc teams promote fun above winning. From $650, all-inclusive.