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So many boaters—new and experienced alike—are signing up for instructional charters right now that Offshore Sailing School, the official sailing school of The Moorings, is running out of instructors to teach them all.

“We have more boats than we have instructors,” says Beth Oliver, Offshore’s director of marketing. “We would hire five more tomorrow if we could find them.”

It seems that Americans decided to learn far more than sourdough bread-baking during the pandemic. Whether it’s new boaters trying to learn the basics, or experienced boaters getting wheel time on larger or different types of vessels, or longtime boaters seeking education about everything from celestial navigation to bluewater passagemaking, companies that provide instructional charters in Florida, the Bahamas and the Virgin Islands are reporting unusually high and steady demand for bookings.

An instructor can expose less experienced sailors to gear they may have never used before.

An instructor can expose less experienced sailors to gear they may have never used before.

“The big thing now is that everyone and their brother wants to buy a boat and do the Loop,” says Barb Hansen, co-owner of Cape Coral-based Southwest Florida Yachts. “They may not even know what the Loop is, and they want to do it.”

As with Offshore Sailing School, Southwest Florida Yachts has seen a consistent stream of customers wanting to book a week aboard one of the company’s boats for a combination of warm-weather cruising and on-water education. In some cases, Hansen says, someone wanting to take out one of the fleet’s larger boats—a Grand Banks 42 Classic or a Beneteau 44 Swift Trawler, for instance—will want a captain on board for the first couple of days to get comfortable, prior to the rest of the week spent on a bareboat vacation.

“Let’s say the person has a Sea Ray 30 or 32 up in New Jersey, but they’ve never really handled a big trawler here in Florida,” Hansen says. “That type of person would only need a captain for a day or two. They’re used to navigation, they’re familiar with weather conditions, docking the boat, anchoring and so forth. A boater who just trailers a boat from place to place doesn’t really have that same kind of experience. That’s why, when helping customers choose an educational charter, we ask people not just what kind of boat they have, but what kind of cruising they’ve done.”

Instructional charters can be tailored to focus on all kinds of skills, Hansen says, depending on what the boater wants to learn while cruising in Southwest Florida’s warm waters. “There are a lot of people who’ve never anchored out, who just go from dock to dock. Some are expecting mooring balls, but down here, it’s a lot of anchoring,” she says. “Some people are a little intimidated, so you can work on that with the captain for the first couple of days.”

Mark Gonsalves, co-owner of Cruise Abaco in the Bahamas, says his fleet of 21 boats includes four power catamarans that are used for training during weeklong bareboat charters. “What’s unique about our program is that it’s captain by day and bareboat by night,” Gonsalves says. “Every night, you’re at a different island, and a chase boat picks up your captain so you’re on your own. You get a great vacation too.”

Quite a few of the instructional charter clients at Cruise Abaco are owner-operators, he adds. “A lot of our people own boats somewhere else,” Gonsalves says. “What I hear is that they want to come and experience the Abacos, maybe do a test run to brush up on their skills before they retire and come down with their own boat.”

The Moorings and other charterers are reporting a significant uptick in demand for instructional charters.

The Moorings and other charterers are reporting a significant uptick in demand for instructional charters.

Oliver says that Offshore Sailing School—which offers various courses aboard different types of boats depending on which Moorings base the student chooses—can tailor courses for couples or families who book a whole boat, but who are at different experience levels. “We have to teach to the US Sailing curriculum,” she says, “but if someone needs more navigation or more docking or more of something else, as long as they can demonstrate their proficiency, then we can work to their level.”

Offshore Sailing School also offers advanced-level courses for experienced boaters who have completed prerequisite classes. Those advanced courses include performance racing off Florida’s Captiva Island—this year, with America’s Cup and Whitbread sailor Dawn Riley—as well as coastal navigation, coastal passagemaking, celestial navigation and offshore passagemaking. And, the company puts together flotillas several times a year for boaters who want to cruise with other yachts from a Moorings or Sunsail base. Each flotilla follows a lead boat, helping participants to learn a new region and offering support as needed. In 2022, there are four flotilla charters planned, in Sint Maarten, Thailand, Croatia and the Seychelles.

“People will meet on the flotilla, and then call us from the place they’re at. They’ll say they are all enjoying each other’s company and want to plan a trip together the following year,” Oliver says. “It’s like a reunion. We have one woman who plans her entire vacation for the year with us. She has five weeks off, and she’s going on five of our flotillas. It’s a ton of fun.”

Hansen says demand is so high for bareboats and instructional charters right now that some experienced boaters who book through Southwest Florida Yachts are even switching (albeit temporarily) from diesel to wind power. “We’ve had powerboat people ask for a a three-cabin boat for three couples. If there’s no powerboat available, they’ll take the sailing cat and they just motor the whole time,” Hansen says. “We might put a captain on with them for the first day to get them comfortable with a 25-foot beam, but other than that, they’re fine. They just want the boat for the comfort, really.”

Gonsalves says that Cruise Abaco, which opened 19 years ago, is seeing so much demand that he just hired three new captains. “We were at 12 boats last year, and we’re going to be at 21 this year,” he says. “We still have availability because we added boats to the fleet.”

Offshore Sailing School, too, sees no sign of demand slowing. “Typically, we
charter a sailing catamaran and a monohull from The Moorings down in the British Virgin Islands. We actually operate our sailing courses out of Scrub Island, which is a private island off Tortola,” Oliver says. “We feel bullish enough about demand that we’re now chartering a powercat every week of the year, just like we do with the sailing cat and the monohull.”

The students booking instructional charters from that location, she says, now range from people who once sailed a Hobie Cat at summer camp during childhood to families of owner-operators who want to improve their skills while enjoying a winter getaway.

“We’re seeing people who want to get into it, and we’re seeing people who want to do more of it,” Oliver says. “We also have reciprocity, so you get up to 15 percent off your first charter with The Moorings if you’re an Offshore Sailing School graduate. It’s not an activity; it’s lifestyle.” 

This article was originally published in the December 2021 issue.

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