On the Water with Sean Bolebruch of Sail Rockaway
Words and photos by Reid Cashour
We caught up with Sean Bolebruch, the passionate founder of Sail Rockaway. Discover how he transformed his love for the sea into a thriving sailing business on Jamaica Bay.
John F. Kennedy Airport’s tarmac is a few miles away, with a choreographed barrage of planes taking off and landing. Across the Jamaica Bay, on the north side of the Rockaway Peninsula, quietly sits Marina 59 where a healthy variety of houseboats, fishing boats and a couple sailboats line the docks. A small minority of New Yorkers own or rent waterfront property within the five boroughs of New York City. Sean Bolebruch, founder of Sail Rockaway, has resided in a modest home in Averne Queens for over a decade. He lives steps away from the rich ecosystem of Jamaica Bay: birds, marine life and ample vegetation. Sail Rockaway offers sailing tours, lessons and boat rentals on the Jamaica Bay. This includes sunrise, birding, sunset and moonrise tours.
He’s a fine sailor who does not wear sunglasses and always sports a hat or visor. I learn something new every time I am on the water with him in his elegant 17’ Norfolk Oyster. During a sticky, overcast Saturday afternoon in July, I sat down with Sean to pick his brain. As we started, a cat crosses the parking lot and finds shade under an outboard propeller.
Where did you grow up?
I grew up in Port Washington, New York, which is on the north shore of Long Island. Just it's basically a peninsula that juts out into Long Island Towns was surrounded on three sides by water, and has a really nice harbor there called Manhasset Bay with a really solid boating community and an awesome place for a kid to grow up. There are so many different little areas by the water that you can explore and kind of go do boating on your own and lots of forests and hills and really grateful for the Port Washington.
Is the sailing community still strong there?
100% Oh, yeah. [Boeing 737 soars overhead] It always has been there's like probably four yacht clubs there within a stones throw of each other. So they're always traveling around to do regattas is with other yacht clubs up in Connecticut and further out in Long Island. Basically, Manhasset Bay is the last good harbor before you get to New York. So once you pass and Hudson Bay heading towards the city, there's no good harbors. Like there's like Flushing Harbor or Douglas Harbor or something like that. It's not very well protected so it's really the closest good harbor to New York City. So a lot of people who live in the city will actually keep their boats in Manhasset Bay.
What brought you out to Rockaway?
What brought me out to Rockaway was the fact that when I moved here in 2009, I was paying $1,400 for a three bedroom apartment that was one block from the beach. So it was really cheap to live here but my primary reason for moving out here was just so that I could surf. I was strictly devoted to that endeavor at that point in my life.
How long have you been in Rockaway for?
I've been here since 2009. So I guess 2024 Right now, so coming up on 15 years.
And when did you start Sail Rockaway?
No one was doing any sailing commercially in the bay at that point. I had a nice little boat that worked really well in Jamaica Bay and I just said to myself, this would be good. Maybe have some passengers, paying passengers, and show them all the little secrets that we have out here. It's not crowded and a really great place to cruise, I mean, it's almost better than where I grew up, Manhasset Bay with the strong boating community, but it's crowded. There's boats, like all over the place, you come down here, like, most days, I'm the only boat on the water. And so I've got the city skyline in the background. So it's just a really great place to do that.
How did you acquire your current fleet starting with Christina?
So Christina, that was actually my family's boat, and they were not using it anymore. You know, like, as the as is the case with most boat owners, you use a lot in the beginning, the first few years, and then you sort of tire unless you of course do long distance trips to new places that boats too small to do that kind of long distance. My father essentially sold me Christina. And then my second boat, I got that off of Craigslist, from an 80 year old chemist down in Philadelphia. And you know, he's a chemist, so he just meticulously maintained this boat. He got it from the first owner, it's a Drascombe Lugger. The first owner was actually the dealer for Drascombe boats in the US. So back in 1973, when Drascombe first decided to start shipping boats over, the first owner of that boat was the dealer. That's actually the first Drascombe Lugger that was shipped over to the US. That particular model of boat is beloved around the world. It's there's like tons of articles about it. This famous sailor named Webb Childs, who's done several solo circumnavigations around the world, actually attempted one of his circumnavigations in the Drascombe Lugger. It is not meant for that kind of sailing at all, but people just loved that boat so they did just about everything.
To transition, what made you want to start the youth sailing program?
There's just no youth sailing programs on Jamaica Bay. Even though New York City does have that sort of thing, those programs take place in the New York Harbor and on the Hudson River and areas like that, where it's just not the kind of place you want to go swimming. There's tons of boat traffic and so to have a kid sailing program in New York City here on Jamaica Bay, in my opinion, is the best place that you could have that kind of program. No one was doing it and we have all just beautiful wind, open waters, and it was just a no brainer. There's tons of kids that I know, like, lots of my friends are parents. So yeah, it just kind of all fell into the right place, you know?
How many youth sailors are registered right now?
We have six kids in the morning. Group of six kids in the afternoon. So that's what we have right now. This is the first official year that we're doing it so trying to keep it a little bit on the small side. It's not officially a camp, so when you have an official camp in New York City, you have to like, abide by all these regulations. So basically, they're just 6 passengers that I take on.
What do you see for the future of sail Rockaway?
[Seagulls chirp in the distance] Well, I don't want to get ahead of myself and I'm always a little bit weary to start talking about stuff before you actually, you know, initiate the plan. What I would like to see whether I'm the one who does it, or somebody else is a community based sailing organization, that is probably along the lines of a nonprofit, so that they can offer free lessons and experiences to the local youth and the people of this neighborhood. Because we have, I want to say around 600,000 inhabitants here on the Rockaway Peninsula and on any given day, there's probably no more than 30 Rockaway people out on the bay, you know what I mean? So, I want the people who live here who are surrounded by this water, to be able to experience it and we can teach them how to swim, we can teach the youth the skills that can help them to segway into the maritime industry as they grow older, because there's tons of job opportunities in the maritime industry. [An airbus roars above us] So not so it's not just for fun and to have a good experience but actually to create jobs by bringing people in water and teaching everything that goes along with that.
All right, well, we'll get a little more fun here. What's your favorite food or restaurant in Rockaway?
My favorite restaurant in Rockaway is Whit’s End. by a longshot and my favorite food in Rockaway is probably the burger at Whit’s. Yeah, he calls it the fucking good burger and it really is fucking good. It's not one of those smash burgers. It's like a nice juicy burger.
Speaking of food, tell me more about the oysters you sell? Where do you get them and where do you sell them?
I get oysters from the Peconic Bay. I also get them from Oysterponds Shellfish Company based in Orient New York. So in my opinion, like that's probably the cleanest water that you can get the oysters from. I also get it from Matt Ketchum who runs Peconic Gold Oysters. He has a really great way of cultivating his oysters. He uses roll cages which keep the oysters nice and uniform.
The reason I sell the oysters is because I think it's a power food. You only have to eat a couple of oysters and you've gotten some serious nutrients, such as zinc. I started selling oysters during the pandemic. If you eat four oysters, you've just gotten in the amount of about 600% of zinc that you need for a daily allowance. Zinc helps to fight off bacteria and viruses and in terms of skin repairs, is one of the most critical vitamins for skin. A lot of sunscreen is made of zinc.
Where do you sell the oysters?
I was selling them at a farmers market called the Warehouse Market, but they moved locations, so not convenient for me to do it. I would just have people come into the marina and they could pick them up for me for a good price.
What was the most undesirable place you've sailed?
Two places. One place was the Arthur Kills, which is the creek that separates Staten Island from New Jersey. When I finished traversing the creek, the hull of my boat was brown and there were really big freight liners that come into New York Harbor. They're all up on that creek and that creek is probably at its widest point, maybe like 200 feet. So there's just massive ships and then there's just like little ol’ me traversing that.
The second place that was the shittiest. This is going to come to a surprise to a lot of people but it was actually Port Jefferson. The locals there were super unfriendly and unwilling to help me. It’s a tiny little town and hundreds of ferry passengers coming through the town. The locals are jaded and if you're not a local there or if you just need help, they’re like “Sorry, buddy, we were not going to help you.” I tried getting a water taxi and they asked “What kind of boat are you want? I say, “I'm on a 17 foot sailboat.” They're like, “Yeah, don't think we're gonna help you.” Then I anchored my boat, outside of the main acreage, acreage, because I needed to there was a storm. And I read the town by lines, all the rules which govern how you can integrate stuff. I was totally late to anchor there because I needed to take shelter from the storm and the Harbormaster came over to my boat the next day when I was off it and put a sticker on my transom, damn near impossible to remove. It said, If you don't move your boat in, like 24 hours, we're gonna seize it. I was in my right to be there.
Let's flip it, what was your most favorite place to sail? I know you went to the Caribbean this past winter?
I mean, obviously the Caribbean is a top choice, right? But that's an easy answer. So but I think just speaking locally, my favorite place to sail is probably Jamaica Bay. It's very big. It's really well protected. It has tons of little areas to explore and if I was to venture outside of Jamaica Bay, I probably say the Peconic Bay, the one that's between the North Fork and the South Fork is very similar to Jamaica Bay. There's a little nooks and crannies and little places to explore and open water to just cruise.
What's the furthest sail you've done?
When I circumnavigated Long Island on my 17 foot Norfolk Oyster and took about three weeks , I took my time. I went up to the Connecticut River for a little while, just because I was in the saltwater for like two weeks and I needed a little bit of freshwater. Oh, I've sailed from North Carolina to New York before so that was technically longer but like straight sail, we weren't even near land and in the open ocean all the time.
So when you sailed when you circumnavigated Long Island, did you stop in certain places?
Yeah, I spent about three days on Fire Island and then spent a few days out in the Hamptons and then I went up into the Peconic Bay. Spent five days up in the Peconic, then Shelter Island and had my girlfriend at the time come meet me. We stayed in the Rams Head Inn on Shelter Island. It only rained once the entire trip and my boat doesn't have a cabin. So I just anchored the boat underneath a small bridge and it protected us from the rain. It was the most perfect trip and yeah, I really had a good time.
Sky's the limit. What's your dream boat?
I used to think about that a lot. But it's probably like a Southern Cross, or something like that. Just like a nice blue water sailboat. I don't really think about that anymore. I used to think about it and it was just too distracting. Yeah, you know, I think I have my dream boats here to be honest with you.
What else do you do when you're not sailing?
I surf, maintain my boats and like to take little trips back up to where I grew up on the North Shore of Long Island; and just go swimming in freshwater for a change. Wash off all the salt.
Any shoutouts?
Yeah, I want to give a shout out to Sam Jackson, who has been steadfast in helping me run the business for the last two years. My father John, who basically taught me how to sail and has been sticking by my side the whole entire time. My crew in Brooklyn, the Rakit Club crew, with Shiva and Micha and all those guys and my family, you know, my my aunts and my uncles. Katherine Coates, for designing my website. God bless all of them.
Follow Sail Rockaway's Instagram here.
