On the second afternoon of a Chicago-Mackinac race that would be remembered as one of the fastest in years, most of the 326-boat fleet was charging up Lake Michigan in a 20- to 25-knot southerly breeze with chutes full and a building sea pushing down waves. The 10 sailors on the 1D48 WhoDo were enjoying their own rollicking ride as they entered the Manitou Passage about two-thirds of the way up the course when a gust buried the boat’s bow knocking it down and causing it to round up only to get knocked down on the other side. 

Have you ever used a scythe, Nic?” asked Cathy Mac Aleavey when I met her at Jimmy Furey’s house on the banks of the River Shannon in Ireland last summer. Now, I’ve been to dozens of sailing events around the world, and I’m pretty sure I’ve never been asked that question before.  

 You can’t escape history when sailing in the Mediterranean, not even your own. We were off the Lycian coast of Turkey. My wife Tadji was at the helm, searching for zephyrs as Quetzal ghosted over a shimmering sea. I was below, rummaging through the nav station looking for a detailed chart for the approach to Kekova Roads. I am a luddite, I still use paper charts and I knew it was in there somewhere.

Revolutions aren’t always noisy, colorful affairs. Sometimes they start with just a ripple, a whisper—or the sound of tiny plastic balls hitting the ground.

For many would-be sailors, their first sailing experience will come in a formal learning environment with an instructor guiding them through it. Sailing instructors are ambassadors of the sport and may be one of the most important factors in whether someone becomes a lifelong sailor or returns to their landlubber roots. It’s a tall order for instructors, who take the responsibility seriously. Every year, thousands of sailors take a class to learn new skills or improve and expand their sailing knowledge, but how do you know you’re getting the most out of a learning experience?

 Come back alive, and bring the boat back alive.” Over and over those words played through Hobie Ponting’s head as he boarded a plane to England. He and his team had set off to Hamble, England, to take delivery of a Class 40 sailboat that had been donated to Oakcliff Sailing. The plan was to return to the States via the inaugural Royal Ocean Racing Club Transatlantic Race, departing from the Canary Islands and finishing in Grenada. None of them had ever sailed a Class 40. None of the crew had ever crossed an ocean.  None of them knew what awaited them other than 7,000 miles of ocean sailing.

 For many sailors, the dream of boat ownership is always present. But making it a reality means overcoming the big fear: the terrifying possibility that you could plunk down a fair amount of mone

Cruise the beautiful Beagle Channel, including possibly sail around Cape Horn, with Skip Novak's Pelagic Expeditions.

 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.

Twenty years ago, I was working at the office of Classic Boat magazine when I got a call to review a boat on the River Dart. It was the latest design by that doyen of modern multihull design Nigel Irens, best known as the designer of ENZA, Ellen MacArthur’s record-breaking B&Q and several Gunboat multihulls. 

Whether your boat has enjoyed a winter off or it’s time to take on some annual chores, our guide to fitting out will make sure your boat is ready for a great year of sailing

When a cruising tale starts with the words, “We had no engine and ... ,” it usually means a disaster story is about to follow. Most sailors get a knot in their stomach at the thought of losing an engine while trying to anchor somewhere new, entering a busy harbor at night or attempting to dock their boat. Those are the panic-inducing moments that we prepare for but secretly hope never happen. There are some sailors though who go through these scenarios on purpose. Sailing without an engine is not a new idea, but it’s one that is catching on slowly but surely with long-term cruisers all around the world. 

But never fear; we’ve assembled a list of sailing experiences you can enjoy right now, all of which will help tide you over until it’s time to pull the sails out of storage and kick off the season. 

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.

 The winds were off the starboard stern at around 15 knots, steady and warm on a sunny July afternoon, blowing up Lake Ontario out of the southwest. The water was flat in spite of the long fetch, protected by Amherst and Wolfe islands off Kingston, Ontario, where the Great Lake flows into the St. Lawrence River, starting its 650-nautical-mile journey to the sea. We were bound for the Thousand Islands, a world-class cruising ground with a wealth of anchorages and a multitude of delights. 

The cruiser-racer fleet grew in the 1908s and 1990s and the boats of that era continue to cruise and race successfully today.Erik Simonson photoYou still see them at local marinas and at popular dista

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.

Our editors choose the best sailorly gifts to give and get this season.