Charter and privately owned boats that had been moored in the hurricane hole at Tortola's Paraquita Bay are stacked on top of each other following the passage of the devastatingly strong Hurricane Ir

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. 

 My definition of “boat” entails three essential capabilities—flotation, propulsion and steering. If you lose one of these, things are going to get difficult. We all know about keeping the water out, the rig up, and engine working, but we tend to take steering for granted. I have had a wheel go loose in my hands, and I can attest to the helpless feeling that accompanies it.

As the American Sailing Association’s affiliate representative, Elbert “Ash” Ashbaugh sees a lot of sailing school applications come across his desk. Many are from schools that have been successfully operating for awhile, complete with professional offices, insurance and the right boats for teaching; he might be able to get their applications approved in just a week.

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.

Bermuda’s 22-year-old MacKenzie Cooper was on top of the sailing world as his Team BDA stormed across the finish line in first place in the first race of the Red Bull Youth America’s Cup finals in June. Held in conjunction with the America’s Cup on Bermuda’s Great Sound, the youth series pitted 12 teams from around the world against each other in an exciting fleet racing format that saw eight finalists on the line in a jaw-dropping display of speed, seamanship and sportsmanship. As Cooper’s boat crossed the line, the stands erupted in a sea of Bermuda flags while most of the tiny country’s population of 65,000 stopped what they were doing to cheer on the local favorites.

Mark Wheeler knew that staying calm was key. That’s easier said than done when you’re in 65-degree Lake Michigan with a storm on the horizon, building seas and you’ve just watched the boat you fell off of sail away at 18 knots.

SEPTEMBER 2017 Table of contents

More than 80,000 people packed downtown Auckland, New Zealand, in July to celebrate the triumphant return of the America’s Cup after a 17-year absence. Thunderstorms didn’t dampen spirits as Emirates Team New Zealand paraded down Queen’s Street, the Auld Mug held high, and onto a boat for a tour of the jam-packed Waitemata Harbour. 

The pilot books and online passage guides all agree: You do not sail across the Atlantic from west to east in a small boat in January, February or March. Even the Admiralty chart of the Atlantic warns sailors not to attempt an eastward crossing in those months. But Susie Goodall, 28, was having none of it. After four weeks in Antigua, mainly taken up with fixing her engine, she set sail on March 20 and, rather than take the recommended route via Bermuda, headed straight for the Azores. It’s known as the “devil-may-care” route and cuts 500 miles off the crossing, but also increases the likelihood of running into Atlantic gales. Which was exactly why she did it. 

Les Crane sat on the deck of an unfamiliar boat in the middle of the Atlantic Ocean watching his boat, a sturdy, well-maintained 56-footer that he’d sailed more than 40,000 miles, as it was swallowed by the water. It was 7 a.m., less than four hours after his crew heard a “thud” that they had no idea would lead to them boarding a life raft and waiting for rescue.

Sailing at night is challenging, rewarding and dermatologist approved. Gliding through the dark under the stars can be a surreal experience. And you don’t have to go very far from the harbor for the experience. It is a different world that requires new skills and awareness to be fully enjoyed. 

Like a sailboat, life never moves in a straight line from the starting line to the finish. It also has a tendency to blast you with roaring winds, strange currents and a startling array of unexpected circumstances, which means you’ll learn a heck of a lot along the way—and very likely emerge stronger and wiser than before.

Sailing in light air is a science and an art. The science comes from adjusting your sails and position of sail to get the maximum lift and momentum. The art is the patience and fortitude for you and your crew to remain still, quiet and aware while resisting the urge to reach for the start button on the “Iron Genny.” With some experimentation and focus, you’ll fine that it’s not difficult to keep the boat moving well in light air, and it can be surprisingly pleasurable sailing too. 

When helmsman Peter Burling buried the hulls of his 50-foot foiling ACC catamaran on the way to the start line, lost control and nosed-dived into Bermuda’s Great Sound, there was a chance that the America’s Cup was over for Emirates Team New Zealand. But like Humpty Dumpty, the shore crew picked up the carbon fiber pieces and put the fragile cat back together again, and the Kiwis went on to dispatch the British Land Rover BAR team in the challenger playoffs semifinals, and the Swiss Artemis team in the finals to win the Louis Vuitton Cup, setting up a rematch against Oracle Team USA for the America’s Cup in June.

For years sailors were mostly left to call on experience and instinct when it came to routing a passage. Today, onboard computing power relying on copious amounts of data can show sailors any route with any number of variables applied.

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.

Chris Johnson was bleary eyed as he filled his coffee cup at a popular open-air breakfast spot just steps from the marina at Nanny Cay. He was just one of dozens of sailors gathered in the hub of the British Virgin Islands during the 46th annual Spring Regatta. Like those around him, he seemed to be fully embracing the laid back but fun racing scene that takes over the island for a week each April.