The enticing part of sailing is that every time you go to sea you learn something new. And because sailors aren’t typically people who like to sit idly by on their vacations, combining the two, by learning to sail in a vacation setting, has become an increasingly popular trend.

Sherry Pickett, from Thorn Hill, Ontario, near Toronto, said learning to sail with Offshore Sailing School in the British Virgin Islands was an ideal way to further her sailing skills while enjoying a sailing vacation in the warmth away from the cold Canadian winter. Pickett and a group of woman friends took the one-week Fast Track to Cruising course followed by a week of charter cruising with their partners on three catamarans.

“I wanted to celebrate my 50th birthday last March and also wanted to step up my confidence level on the boat away from the guys,” Pickett said. “I wanted to know I could do it on my own.”

Pickett and her husband Owen started sailing nine years ago when friends invited them along on a charter cruise in Greece.

The group, from left, Carolyn Quinton Smith, Sherry Pickett, Offshore Sailing instructor Folkert Jonkind, Joanne Patriarche and Joanna Thompson, have some post learn-to-sail refreshments aboard the Willy T.

“I love it, but it also scared me a little bit so I wanted to learn more,” she said.

She and her husband took lessons locally, eventually buying their Hunter 34 Undecided, which they keep in nearby Whitby and daysail on Lake Ontario. 

“We chose the Fast Track course because it suited our group, with one of us new to sailing,” Pickett said. “The first two days were spent in the classroom in the mornings and sailing the Colgate 26 in the afternoon. It was a terrific refresher for all of us.”

The group spent the final five days of the course liveaboard cruising around the BVI. The students, who had sailed the area before, had input into the destinations, but Pickett said it was a bonus to have a knowledgeable skipper with experience in the area.

“We went to our favorite spots like Cooper Island and White Harbor, but he guided us to a tricky anchorage on Virgin Gorda near Scrub Island that was really neat.”

There was some down time during the week of cruising, heading to local beach bars and the Willy T. in the evenings, but Picket said the learning was tiring.

“We made up for the next week when our husbands joined us for a week of cruising,” she said. 

Offshore Sailing School, founded by Steve and Doris Colgate, is celebrating its 55 anniversary. From bases in Florida and the British Virgin Islands, the company offers a full range of courses, from beginner to offshore passagemaking with curriculum designed by the Colgates and US Sailing. Introductory level courses are taught aboard the Colgate 26, a training daysailer designed by Steve Colgate and Jim Taylor specifically for the company. The company offers a variety of courses on Moorings charter boats at its Scrub Island base in the BVI, which students can sign up for as individuals or as a group. One of the most popular courses is the Fast Track to Cruising course that Pickett took.

Morning lessons take place in paradise on Cooper Island.

“We did a lot of things like person overboard drills and other safety tips, but a lot of it was just tweaking the things I was unsure about and confirming the things I already knew—all it was confidence-building.

“I’ve never been racing, so one most interesting things I learned about was sail trim,” she said.  

Pickett’s husband Owen is now currently signed up to take the same course this season in order to catch up to her level so they can go on to take the next offshore passagemaking courses together. While they have no great plans to sail off into the sunset at this point, Pickett and her husband hope to one day sail their own boat to the Caribbean. In the meantime, Pickett credits the emphasis placed on navigation and route planning in the course to the biggest change in their sailing on home waters.

“We had previously only done a few overnights, but this last summer we took a two-week cruise on Lake Ontario, and went all the way east to the Bay of Quinte.”