Alexander Dunayski is the owner of "the Moose," a 23-foot sailboat moored off of Sheepshead Bay, Brooklyn. Here, he goes by Captain Alex.
One Thursday in September, I booked a 2-hour sailing lesson onboard the Moose, his 1966 Pearson Ensign Daysailer, through Boatsetter. 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 "summer of sharing," you can now rent a stranger's home, pool, car, private gym and yes, even their sailboat. A decade ago, this level of intimacy among 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 coverage, reviews, and in-app messaging, the start-up has successfully convinced boat owners and landlubbers alike to trust strangers on board multi-million dollar vessels in the middle of the sea.
On my first time using the app, I was able to easily navigate 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 listing within my budget was the hardest part of the whole process. The advertised hourly rate was far less than the final charge at check-out as most listings had a two to three hour minimum, plus a captain fee. The Moose was the least expensive 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 City, I met Alex at the address listed in my trip itinerary and messaged him through the app upon my arrival. Our voyage then began at Miramar Yacht Club, founded in 1944 by a group of Jewish sailors who were barred from joining the local yacht clubs at the time. The organization still advertises itself today as "a haven for sailors of every ethnicity and race."
"I call this the Brooklyn riviera," Captain Alex said as I steered us between Rockaway and Manhattan Beach, kicking off my tour of the South Brooklyn coastline that ended at Coney Island.
Once Alex discovered I already knew the basics of sailing, he let me take over as skipper. Along the way, I learned how to do a "heave to" maneuver and how to better navigate switching wind patterns.
Despite his expertise and passion for sailing, Alex didn't grow up around the sport. In fact, he didn't step foot on a sailboat until he was 40 years old at the behest of a friend.
"Once I stepped on board I was hooked," he said. "I don't know, maybe I was a pirate or something in a past life."
Before a serious back injury, Alex said he enjoyed jet skiing and more physically intensive water sports. Now, he takes out the Moose up to twice a day if the wind is good and the sun is shining.
He loves to teach first-time sailors but it's tough to get students, he said. Most New Yorkers prefer sunset booze 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 off the bow, which Alex called a Goose (because it rhymes with Moose).
"Remember we have company in the back," he told me as I attempted to tack out of the harbor, docking 20 points from my score as the Goose bumps off the side of a mooring.
Then there's the Nutella Kinder bars packed in a cooler, plus complementary photos Alex takes along the way — his "real" job, as he calls it, is a commercial real estate videographer.
The 2-hour lesson was $350, a steep price for one person — but more affordable for three or four, he points out, which is more common than our private weekday lesson. Boatsetter takes a 10% cut, according to his receipts.
Captain Alex doesn't get enough bookings through the app to make a real living, but that's the dream. He's taken out tourists from Australia and local children whose mothers were desperate to get them away from screens.
"It gives an average boat owner and average guy a way to make an extra living doing maybe what they love," he said. "A guy like me, I wouldn't be able to get clients just like that."
On the user end, the voyage was a frictionless, convenient way to escape the New York City heat and get out on the water. Boatsetter is a prime example of how technology can facilitate memorable, in-person experiences. I'll take that over sailing in the metaverse any day.