Car bookings

I booked a two hour sailing lesson with the Boatsetter app

  • Peer-to-peer boat rental app Boatsetter raised $38 million this summer.
  • I used the app to book a $350 two-hour sailing lesson in Sheepshead Bay, Brooklyn.
  • It was a great way to escape the city heat and get out on the water – here’s what it looked like.

Alexander Dunayski is the owner of “the Moose”, a 23-foot sailboat moored off Sheepshead Bay, Brooklyn. Here it goes through Captain Alex.

On a Thursday in September, I booked a 2 hour sailing lesson aboard the Moose, his 1966 Pearson Ensign Daysailer, through Boat builder. The watercraft rental platform has raised $70 million in funding in hopes of becoming “the Airbnb of boats” and currently has 50,000 listings in 700 locations around the world.

Amid what Axios described as the “the summer of sharing”, you can now rent a stranger’s house, bowl, car, private gym and yes, even their sailboat. Ten years ago, this level of intimacy between strangers would have been unthinkable, if not downright discouraged. Now, with a user-friendly app for every exchange, making connections like my excursion with Captain Alex is more accessible than ever.

Thanks to things like insurance coverreviews and in-app messaging, the startup has managed to convince boat owners and earthlings alike to trust strangers aboard multimillion-dollar ships in the middle of the sea.

Miramar Yacht Club, Experiential Boatsetter


Hannah Towey / Insider


When I first used the app, I was able to easily navigate through the different experiences offered in New York, from fishing and sailing to sunset cruises. Then I requested a date and time for my lesson, which was confirmed the same day.

Finding a list within my budget was the hardest part of the whole process. The advertised hourly rate was much lower than the final rate at check-out, as most adverts had a minimum of two to three hours, plus a captain’s fee. The Moose was the cheapest listing in my area – in total I was charged a $150 boat fee for two hours, a $150 captain fee, and a $50 service fee.

Once in the far reaches of New York, I met Alex at the address listed in my travel itinerary and messaged him through the app when I arrived. Our journey then began at the Miramar Yacht Club, founded in 1944 by a group of Jewish sailors who were barred from joining local yacht clubs at the time. The organization still presents itself today as “a haven for sailors of all ethnicities and races”.

Boatlayer Screenshots


boat builder


“I call it the Brooklyn Riviera,” Captain Alex said as I headed between Rockaway and Manhattan Beach, kicking off my tour of Brooklyn’s South Shore that ended at Coney Island.

Once Alex discovered that I already knew the basics of sailing, he let me take over as skipper. Along the way, I learned how to perform a “swell to” maneuver and better navigate changing wind regimes.

Despite his expertise and his passion for sailing, Alex did not grow up around this sport. In fact, he only set foot on a sailboat at the age of 40 at the request of a friend.

“Once I got on board, I was hooked,” he said. “I don’t know, maybe I was a pirate or something in a past life.”

Boatlayer experience


Insider / Hannah Towey


Before a serious back injury, Alex said he enjoyed jet skiing and more physically intensive water sports. Now he takes the Moose out up to twice a day if the wind is good and the sun is shining.

He loves teaching new sailors, but getting students is difficult, he said. Most New Yorkers prefer sunset cruises to learning how to sail an old boat – which is why he tries to make the 2-hour lesson more fun than stressful.

That’s why there’s an inflatable swan floating in the bow, which Alex called a goose (because it rhymes with Moose).

“Don’t forget we’ve got company aft,” he told me as I tried to tack out of port, docking 20 points to my score as the Goose hit the side of a mooring.

Then there are the Nutella Kinder bars packed in a cooler, plus some complementary photos that Alex takes along the way – his “real” job, as he calls it, is a commercial real estate videographer.

Boatlayer experience


Hannah Towey / Insider


The 2-hour lesson was $350, a hefty price for one person — but more affordable for three or four, he points out, which is more common than our weekday private lesson. Boatsetter takes a 10% discount, according to his receipts.

Captain Alex doesn’t get enough in-app bookings to make a living, but that’s the dream. He took Australian tourists and local children whose mothers were desperate to keep them away from screens.

“It gives an average boat owner and an average guy a way to make a living doing maybe what he loves,” he said. “A guy like me, I wouldn’t be able to have clients like that.”

From the user side, the trip was a convenient, frictionless way to escape the New York heat and get out on the water. Boatsetter is a great example of how technology can facilitate memorable in-person experiences. I will support this to navigate the metaverse any day.