There was some breeze early. A four-hour sail turned into seven hours. They passed sunset and returned in the dark, ringed by the lights of Boston.
"It was just a beautiful night on the water," Raggio said. Intrigued, he asked the skipper lots of questions.
Thirty years later, he has sailed off both coasts, the Great Lakes, Mexico and the Caribbean, often invited to crew on the sailboats of friends or other boat owners, usually in races. The marketing and communications executive keeps his own 26-foot sloop on Lake George, near his home in the southern Adirondacks, where the season starts in May.
Crewing is a common start. Clubs in popular sailing cities like San Diego, San Francisco and Miami host days where visitors can learn basics or meet owners who may invite them to do little more initially than help balance the boat.
In Annapolis, Maryland, Jeff Jordan said some days he'll see 300 to 400 pleasure boats on Chesapeake Bay, nearly half of them sailboats.
"It's easy certainly in this area to sail without having boat ownership," said Jordan, director of J World sailing, which offers introductory lessons as well as three- and five-day classes that can lead to certificates. "Even in Iowa, at a little sailing club, just go down and be friendly. Someone will ask you if you want to go. ... It's an adult social sport."
For novices who just walk down to the dock, it's more common to get invited on a boat on race evenings, Jordan said. But it can take beginners some time to figure out exactly what the rest of the crew is doing. Jordan said he gets students who've done that and want to be more than just passengers; in a couple days of lessons, he said, they can become competent crew.
On 32-mile-long Lake George, where the season runs through October, Raggio teaches annual spring classes where novices learn the names and uses of the lines, aka ropes; how to manage two sails; and how to steer with the tiller and point the boat.
In two decades, the Y-Knot adult learn-to-sail program there has taught hundreds of novices how to tack and jibe, tie essential knots, and put up and take down the rigging. They use 20- to 24-foot-long sloops defined by their single mast and two sails. Each takes four or five students out for about four hours on three consecutive Sundays. This year, it costs $105.
"It was kind of magical being on Lake George in the sun and the wind," said Diane Fiore, describing her first outing last year. An occupational therapist, she was preparing to volunteer with the Y-Knot program for disabled sailors.
This year, at 52, she's taking the class for herself.
"If you have a wide open space and really get to play around, it's not that complicated," Fiore said.
Raggio loves the quiet of the motor-less boats.
"It's a very back-to-nature experience," he said.
Dan Kennedy teaches disabled sailors in two-seat, 16-foot sloops with simple controls and deep keels that keep them stable.
"It's harmonious," he said of the ancient art of capturing the wind to travel across the water. "It's an amazing technology."
Kennedy and Raggio said the number of sailboats on Lake George has declined. The last company to rent and charter sailboats on the lake stopped last year, they said.
"In the '70s, there were 100 boats on Wednesday nights," Raggio said of the weekly summer races he enters. "Now we see 18, 20, 22."
Kennedy's theory is that Americans have gotten lazier and would rather ride on motorboats.
On Chesapeake Bay, the number of sailboats declined four or five years ago after the recession, but the industry has recovered, Jordan said.
He added that there are, as Raggio has found, sailboats and owners all over. "It's just a giant network and people are always looking for people to go sailing with them."