I have enjoyed a lot of different sailing events, from local regattas to glamorous destinations. Each had its own appeal, but once I’ve been there, done that,  I rarely return because there are new places to explore. But I made an exception for the Golden Rock Regatta, a little-known Caribbean series that is held in November, featuring long-distance races to a smattering of islands: St. Maarten, St. Eustatius, St. Barths and Anguilla. Exhilarating stretches of racing during the day are followed by nightly raft-ups and casual parties. It perfectly combines the thrill of racing with the adventure of exploring a different piece of paradise each night, which has given me the opportunity to forge friendships with other “Rockers” over the years.

What a thrill it brought, pressing my face against a hazy plexiglass airplane window, and seeing whitecaps scattered on the sea from 29,000 feet. Following last year’s tragic season of storms in the Caribbean, I was flying to the British Virgin Islands for the Spring Regatta, which has been bringing sailors to Tortola and the surrounding islands since 1972. As the flight descended through the tropical sky, I began to see the telling signs of destruction. Hundreds of homes were without roofs and scores of boats were askew and aground. But this isn’t a story about destruction. It’s a story about revival, and how sailors are helping bring that about.

The Moorings 4800 rides at anchor.Susan Colby photo Sailing French Polynesia is the stuff dreams are made of. We had Laura, a marine biologist, who dreamed of exploring the sea life and coral gar

Since its first running over a century ago, the Transpacific Yacht Race has bewitched sailors of all backgrounds and ages, to challenge the 2,216-mile course from California to Hawaii. This year’s edition was no exception—a magical experience, for more reasons than you could shake a wand at. There were racers young and old, on yachts large and small, from classic Cal 40s to the record-breaking maxi Comanche. There was a sled with a cat’s name, Pyewacket, and a cat with a monkey’s name, Chim Chim. And this year’s race marked the return of The Wizard.

On a chart, the rhumbline appears as the shortest distance between two points, but when plotting a course through the British Virgin Islands, our “rum line” took a twisting path from one legendary beach bar to another on a weeklong charter cruise. 

Going away to camp is a childhood ritual. There are space camps with real astronauts like Scott Kelly, tennis pro camps, celebrity baseball camps and even a football academy where Tom Brady could be the coach. So why not a yacht racing camp with the pros? The Bitter End Yacht Club’s annual Pro-Am offers just that, inviting top sailors from an array of disciplines to sail and compete with campers. But the event has one exceptional twist—it’s for grown-ups.

For 30 years, sailors have escaped the clutches of Old Man Winter by heading south, to the southernmost point in the U.S.—Key West, Florida.

The TP52 Bronenosec zooms downwind at Key West Race Week.Sharon Green photo For 30 years, sailors have escaped the clutches of Old Man Winter by heading south, to the southernmost point in the U.

 The Tobago Cays are a divine cluster of isles in the Grenadines, in the southeastern Caribbean. But their out-of-the-way location can make this piece of heaven a bit hellish to get to. Roughly 30 nautical miles south of St. Vincent and 30 nautical miles north of Grenada, a visit requires a bluewater sail through the passes between the Windward Islands.

Transiting the Panama Canal is a rite of passage that packs a lot into a 50-mile journey. Whether crossing from the Atlantic to the Pacific or vice versa, cruisers celebrate their arrival in Central America by taking this short cut that recently celebrated the 100th anniversary of the opening of a channel cut through mountain and jungle in an engineering feat for its time.

Maybe it had something to do with the bounty of food and drink served. Maybe it was the chill in the early autumn air or something in the green-tinted lake water. Whatever the cause, Blue Chip Fever struck Pewaukee, Wisconsin, in late September.

Reality television show producers could not have dreamed up a more cockamamie set of obstacles than what the 2015 Transpacific Yacht Race served its 60 entrants, racing from Los Angeles, California, t

Careers and years have a way of tugging friends apart. So photographer Bob Grieser’s 29-year-old godson Sean, who had a landmark birthday looming, resolved to gather his pals from all corners of the continent for a tropical vacation. The trip would launch from Grand Abaco Island, one of the Bahamas’ 700 islands and cays that sprawl across 80,000 square miles of the Atlantic Ocean.

 Keeping both partners happy when one finds a new passion is an age-old dilemma; even Penelope stayed home in Troy when Ulysses sailed off. So often, one partner gets hooked on sailing, but their companion doesn’t; one has a boating background, while the other’s water-based activities are limited to the bath.If you’re having a hard time getting your loved ones into sailing, now might be the time to sweeten the deal. Sailing schools exist in every beautiful corner of the world and who can turn down a learn-to-sail vacation in paradise?

Digging deep into a wooden chest filled with doublets, waistcoats, sashes and breeches I found a tri-cornered hat, complete with beaded dreadlocks dangling from its leather brim. Perfect! Along with my plastic cutlass and scabbard, I was a near-clone of Capt. Jack Sparrow. I sauntered out into the bright sunlight to join my crewmates, scrambling over cannons and up ratlines like scurrilous pirates. St. Vincent and the Grenadines served as the primary filming location for “Pirates of the Caribbean” and a dozen years later, we found ourselves romping through several of the remaining movie sets at the town of Wallilabou, aka “Port Royal” in the popular movie series. It was just one of the many treasures we unearthed on a Sunsail flotilla cruise through the Windward Islands.

Flotilla sailing offers the benefit of a built-in group of friends, with many practical advantages as well. Daily weather reports, chart briefings and local knowledge, plus knowing a helping hand is not far away can set your mind at ease, whether you’re a novice charterer, or old hand.