Cigar Aficionado

Bestselling maritime historian Nathaniel Philbrick often charters cruising sailboats to explore the sea passages and coastal scenes that he writes about in books like the National Book Award-winning In the Heart of the Sea and a history of Revolutionary War, Bunker Hill. Sailing helps him bring the past to life. “On a sailboat,” he says, “your senses are all utilized. The wind fills the sail; the boat heels. You’re moving through the water. We’re out in nature, making it happen.” Just like the whalers, Pilgrims and navies of old, and maybe you.

Philbrick has sailed boats his whole life. For those who haven’t and want to take the helm of their own ship, sailing school can quickly build proficiency. For instance Blue Water Sailing School in Fort Lauderdale, with seasonal branches in the U.S. Virgin Islands, the Bahamas and Newport, Rhode Island, offers a variety of one-week live-aboard cruising courses that combine comfortable cruising vacations with beginning or more advanced sailing instruction.

Standing on the deck of one of the school’s cruising yachts bobbing in its slip on Fort Lauderdale’s Middle River, David Pyle, owner of BWSS, says, “By the end of the [beginner’s course] week you should be able to charter a boat on your own and take it out in moderate coastal water.” A typical day aboard consists of a morning in class reading charts, plotting course and learning sailing and boat maintenance basics. The rest of the day is hands-on—sailing, drills, steering, tacking, learning to read the wind, making an anchorage and docking.

Each 40 to 50-foot BWSS boat—the school also teaches on catamarans—carries an instructor certified by the American Sailing Association (ASA) and up to six people—though courses are generally limited to four students. “Quite often a whole family makes a vacation out of it,” he says. “It’s close quarters, but everyone gets their own space.”

By the end of the week, most students step back ashore ready to buy or charter a cruising sailboat of their own. Some continue on to high-seas voyages. “At this moment,” Pyles says, “dozens of our students are cruising around the world with their own boats after starting with our courses.”

Philbrick knows well the feelings that send those skippers out to sea under sail. “You have your own cosmos,” he says. “You get to go on your own adventure.”

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