12 Metre Regatta, Sand Dollar Sports (Cozumel, Mexico)

12 Metre Regatta, Sand Dollar Sports (Cozumel, Mexico)

High stakes sailing races aren't exactly spectator sports – it's tough to float a grandstand, apparently – and few of us will ever have the honor and challenge of trodding the deck of a legit world-class racing vessel. There is one shortcut we know of, though. Just off the leeward coast of Cozumel, Mexico, aspiring seafarers can vie for vacation bragging rights while crewing an actual America's Cup yacht for a mini regatta.

Step up to the challenge, and you and a coterie of your mates can partake in a three-ish hour race aboard either Dennis Connor's Stars and Stripes US 56 (one of four boats built for the heavy winds of the 1987 America's Cup race in Australia) or Canada's True North IV KC-4. Known as "Twelves or "12 Metres," these boats are actually massive 65-foot-long yachts (their name derives from a formula in which the boat's length at waterline, girth, and sail area have to equal 12 meters or less). The design was long used for America's Cup races from 1958 until 1987, when racers switched to faster catamaran styles.

Once captains are named and teams chosen, a toss of the coin determines which boat you'll crew. The race course includes several circuits around a set of buoys, and requires tacking upwind and speeding downwind, all while trying to cut each other off to steal the other boat's wind, and generally get the upper hand any legal way possible. Each boat has a fully trained captain and two professional crew members, with adventure seekers filling the rest of the positions.

The regatta begins with a few strong arms helping to hoist the mainsail up an 85-foot mast. Meanwhile two others must man the main winch and four the primary winches (for you landlubbers: cranks you spin by hand, fast or slow, as the captain directs). Another four crewman handle ropes and cranks in the back of the boat to control the jib sail, and finally a couple more help with the mainsail (oh, and one person keeps time on a stopwatch). For those with no sailing experience, no worries – the pro crew is there to show you what to do and jump in should anything run afoul. This leaves room for a few sailors to drink the cold beer provided, and cheer on their crew, which is harder than it sounds, as wind gusts regularly tip the deck of the boat perpendicular, right down to that blue Caribbean seawater. The sailboats often maneuver within shouting distance and so the captains encourage a suitable amount of trash-talking with the opposing team.

The entire regatta lasts two to three hours, and, during a typical race, the lead will swap back and forth, with the win coming down to the wire. Regardless of who wins, first and second place both get to hoist a celebratory rum punch back at the dock. The race has earned top ranking for cruise ship shore excursions in the Caribbean for 13 years running, and is easily reserved through all the major cruise lines operating there (or via the web or your local hotel). [$95/person; 888-663-3140 or sanddollarsports.com]