7. The Atlantic Challenge Rowing Race
The basics: Racers (either solo, in pairs, or as a team of four) jump in a super-modded dory and row 2,600 nautical miles, from San Sebastian in La Gomera to Nelson's Dockyard in English Harbour -- a natural harbour in freaking Antigua. The race is based on a route that Sir Chay Blyth did in '66, and you can row, row, row that boat this December.
Where to get your beak wet: The Inn at English Harbour; once rowers start to arrive, the celebration kicks in. After denying your offers to shotgun a beer, the rowers will undoubtedly be exhausted, but a huge chunk of the community will be there to stay up all day/ night and welcome incoming boats.