We’ve been to plenty of concerts but never by sailboat, so when our friends in Florida called to ask if we wanted to join them to see the Dave Matthews Band via boat, we grabbed our bags and headed for the airport. 

 In the winter of 1956-1957, my grandfather commissioned a small sailing craft and named her for the young girl in Charlotte’s Web. He had been dreaming about small boats for some time and the popularity of his second children’s book made the project possible. He had owned other boats, including, a 30-foot double-ended cutter called Astrid, but Fern would be the first boat built for him. 

Jimmy Buffett's newest boat is a cruiser created by a designer known for classic lines and inspired by paddleboarding and surfing.

It was hazy, hot and the air was still and the seas were calm; certainly not the conditions we were expecting as we motored down the narrow channel toward the northern city of St. Petersburg on the eastern edge of the Baltic that so many of us had traveled so far to visit. But the uncharacteristically warm and sunny weather was only the first salvo of what proved to be a barrage of sensory overload that no reasonable expectations could live up to.

 Francis Lee was named in honor of a father’s boating lineage, but everyone knows her as Sliver. To the dockside crowd of sailors who reveled in the champagne-soaked launching, Sliver was celebrated as a hometown wonder designed and built in the Pacific Northwest. The wood composite 62-foot double-ender was designed by Bob Perry and built at Northwest School of Wooden Boat Building.

SAILING's editors round up some of the best new boats you'll see at boat shows this fall. Click through to see them all. 

The crash may not have been heard by all the competitors as the two A-Class catamarans collided at the windward mark on the first day of racing, but by the time the boats hit the beach, every sailor in the fleet was ready to help repair the damage.It’s clear to even a casual observer that there’s something special about the people in the singlehanded A-Cat class. During a break in the action at the class’s North American Championship in Panama City, Florida, the St. Andrews Bay Yacht Club lawn was crowded with sailors helping patch up the boats damaged in the collision earlier in the day. 

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.

Most people are familiar with the three largest islands claimed by the United States—Hawaii, Puerto Rico and Kodiak. In fourth place is Prince of Wales Island, located on the south end of Alaska’s inside passage, and I am grateful for the relative anonymity of this remote Alaskan Island. 

Melges 14 This singlehander was designed Reichel Pugh Yacht Design, the same firm that designed the Melges 32 and Melges 24. 

It’s been a tough decade for sailing. Between 2004 and 2014, one-design class participation declined 12%, and according to US Sailing, this is reflective of the sport as a whole. One-time and would-be sailors are still reeling from the recent recession’s economic aftershocks, and they’re experiencing dwindling amounts of free time while facing an exploding number of options for the limited time that’s left. Longtime sailors have left the sport, youth sailors stop after college and newbies are staying on land.

 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?

 On September 4, 2012, best friends Jessie Zevalkink and Katie Smith cast off the docklines in Northport, Michigan, aboard a capable pocket cruiser named Louise. The 23-year-olds had little sailing experience, yet they were determined to tackle one of the continent’s great adventures—the Great Loop.

For half a century, sailing schools have taught people of all ages how to get out on the water. School fleets were often full of aging boats and instructors’ experience could vary dramatically. There was no certification and no universally set standards. We asked some of the owners of the oldest sailing schools in the country what things were like then and what they are like now.

When to reef? Honestly, I wasn't sure. The wind was now up to a solid 13 knots, tickling 15 with every indication of getting stronger. Yet the 35-foot boat with a full-batten, square-top main seemed to be handling everything fine. In fact, as we galloped past Old Mission Light in Grand Traverse Bay, my sister and her daughter, both nonsailors, were below in the galley, happily making grilled cheese sandwiches and tomato soup without a hint of seasickness. Not bad for a sailboat I was originally reluctant to take on a four-day cruise on Lake Michigan. 

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.

Kris Scheppe met his crewmates for the world championship regatta just days before the three men would compete against some of the best sailors in the world. Scheppe, Scott Ford and Jim Kerr had only