It all started back in 1972, when a few friends decided to have a competitive sail from Hyannis to Nantucket. It soon caught on, and what became known as the Figawi Race now makes room for over 200 entrants each year and brings thousands of people flocking to an otherwise quiet island. To many sailors, Figawi Race weekend is more than just a well-known party weekend-it is something they plan their entire year around. Per their website, "The Figawi Charity generates nearly $200,000 per year, and has provided over $2.2 million in support to local organizations that would otherwise go without."
Some perks of the race? Getting into the annual tent party, which has seen the likes of celebrities ranging from members of the Kennedy family to the New England Patriots' Rob Gronkowski.