SAIL.SailMagazine

Each year, SAIL and St. Vincent and the Grenadines offer our readers the trip of a lifetime: a free charter in paradise on board a TMM Yachts charter boat. To win, readers submit their “Top Five Reasons” for chartering in SVG, and we sift through 1,000 essays to pick our winner.

Our hosts, John and Caroline Charnley, and my wife, Caroline, were already swimming in the cool, fresh water, but of course, I just had to jump in from the “cliff” (about 10 feet high) above the pool.

Ironically, many who sail to St. Lucia do so by default, as it has long been the final destination for the Atlantic Rally for Cruisers. Every year the ARC brings well over 200 yachts en masse from the Canary Islands off Africa straight to Rodney Bay.

From my vantage point aboard a Cal 31 sloop sailing out of Southwest Harbor, the cottages look more like castles, with immaculate grounds atop pink granite cliffs that drop into the chilly Maine waters below. The day couldn’t be more perfect for sailing

Australia’s Whitsunday Islands, on the edge of the Great Barrier Reef just off the Queensland coast, are one of those “bucket list” destinations, known far and wide for great snorkeling, great sailing and some of the best beaches in the world.