Raising Sail in the Digital Age: Attracting the Next Generation of Sailboat Buyers

My first sailboat was a used Beach cat (Prindle) in 1986. I was “Gen Z” age at the time. In today’s dollars, about $4500. I launched at ramp. You can get a fun used boat for $4500, and then sell it 10 years from now for what you paid for it, as I did. No ownership obstacle, because it’s not $100,000.

Sailing started with dinghies. We’ve created the obstacle by implying the need for a 40-foot water line and a suite of electronics. Heck, I often don’t turn the electronics on. I’d rather sail by my scenes. Sailing is about the wind and the senses.

Let them worry about a cruising boat when they turn 40. I eventually bought a cruising boat. I have also since downsized to something sporty and more fun to actually SAIL. It’s a bit more, but still cheaper than a car. No obstacle.

I don’t think it’s the money. It’s the flood of competition for their interest. Maybe the learning curve for something you can’t Google. Mostly, I think it is the required investment of time.

I agree with Drew’s comment above. In Toronto we are lucky to have several co-op dinghy clubs as well, so the capital outlay is zero for people to get involved in sailing. At my (non-dinghy) club, we also offer a Co-op membership, which is an add-on to a social membership – again, much lower annual fees and no initiation or boat purchase required (only some sweat equity in maintaining our fleet).
There are plenty of YouTube videos of people living the life on larger sailboats. There are some cruising dinghy videos as well, but these are mostly European and generally feature older folks. This may be a place to start …

We see similar issues in Canada. My Club is Bronte Harbour Yacht Club in Oakville, Ontario which is on Lake Ontario. Our club membership is greying and shrinking. Some members sell their boats and join as social members. Therefore, we struggle to generate enough income to operate at break even. I was wondering if you or any readers know of any yacht clubs that manage a boat share program. I know of a brokerage that does that. If a club were to do it, how would it work? I wonder if we could offer that as a new class of membership where your membership fee would get you access to a boat for a certain number of days during the sailing season. The fee would cover dockage, maintenance, winter commissioning, winter storage and summer commissioning. Members could do some of the work as volunteer hours. Some work would be sourced to specialist, such as engine and electronics work. The fee also give the person/family rights to year round membership to the club.

If anyone has experience with this type of arrangement post them here. Or write me at dennis_giokas [at] yahoo.com.

Boston has more than half a dozen shared sailing organizations, from Community Boating on the Charles River to Boston Harbor Sailing Club which offers access to cruising boats. Shared ownership options like SailTime also exist. These arrangements offer substantially lower cost, training, and maintenance free sailing. This is where young people, including me, get their start in the sport.

Young people are having a hard enough time paying rent in high priced cities like Boston, never mind buying an expensive toy. Wages have been dropping steadily since the 1980s. Not good news for boat sellers.

Yet, there are big winners in our economy. Boat sellers will have to find these people and meet their needs. These well paid folks work really hard to get ahead of the pack and have little free time. Sailing can offer excitement and the feeling of accomplishment that the successful find attractive.

I think exposure to sailing growing up is key, but at some point there has to be a bridge to a bigger boat. I took my daughter to a sailing class when she was 6, she now runs a sailing school in Minnesota that 1,200 kids go through a summer. But as those kids become teenagers, unless they are in the racing program few keep sailing. If their families have big boats, those are a 2-4 hour drive away on Lake Superior or Lake Pepin — not where their friends are, always the priority for teenagers. And even if they are interested in racing on the big lakes, sports or a million other activities can preclude the time commitment. For 20-somethings there is a bifurcation between 1) the vast majority who are trying to figure out how to live when a one-bedroom apartment costs $1,700 a month and a new car payment $600 a month and 2) the few adventurous 20-somethings who are willing and interested in taking on an old boat. Which brings me to my last point: a new car cost an average of $7000 in 1980 ($29000 in 2026 dollars), average price now is $49,000. I suspect it is even worse for cruising sailboats: listings I see for boats in the 30 foot range that are less than 6 years old are north of $150,000. There is no entry point for a family cruiser that is new (or at least newish) that costs perhaps maybe a little more than a car, whereas in 1980 there was. So if you are on a budget, like most people, your only choice is an old boat that might be a great boat, but is immediately going to entail mechanical and plumbing and other work — and you don’t take up sailing because you like to do plumbing. And by definition you can’t afford to pay the marina $150 an hour if you are on a budget. The lack of an affordable turnkey starter cruiser cannot be helping the situation.

Boat brokers need to push 30ft to 35ft boats (not “racing” boats) and not 45ft +. Just look at the ads in the sailing magazines.