Discovering Brooklyn Sail’s Hidden Gem

As a native New Yorker, I’ve had the privilege of experiencing the city’s vibrant culture and breathtaking views from various angles. However, nothing compares to the sense of wonder and awe that I felt during an evening sailing adventure with Brooklyn Sail. Located at Brooklyn Bridge Park’s Pier 5, this iconic sailing experience is a must-try for anyone looking to see the city from a unique perspective.

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While browsing Airbnb Experiences, I stumbled upon Brooklyn Sail’s listing, which immediately caught my attention. The reviews were filled with stories of people sharing their own experiences on the water, and the availability of after-work departures and weekend sails made it an attractive option for a group outing with my friends. We sent the listing to our group chat almost immediately, and the excitement was palpable.

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Meeting Captain Ian and Boarding the Enchantress

We arrived at the pier picnic bags in hand, eager to start our adventure. Captain Ian, one of the two brothers who founded Brooklyn Sail in 2017, greeted us right on time at 5 p.m. He gave us a quick but thorough safety briefing before heading down to the dock, where he helped us step aboard the company’s boat, the Enchantress. With a classic sailboat vibe, the Enchantress has warm wooden interiors, deep navy cushioned seating, and a cozy layout that doesn’t take away from the feeling that you’re out on the water.

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As we tucked away our bags, kicked off our shoes, and found our spots, Ian cast off the lines, and we slowly pulled away from the marina. We took turns on the cushioned back (where captain Ian stayed, steering the ship), hanging near the mast, and watching the skyline change as we moved further into the harbor. We could have sat below deck, but it was way too warm, and we didn’t want to miss any views.

A Personalized Experience with Captain Ian

The experience felt personal from the jump, thanks in part to Ian’s easygoing presence. It’s clear he’s someone who genuinely loves being on the water and wants everyone to feel safe and comfortable. When I asked if we were going to be able to hear each other talk when out on the water, he let us know that we’d have a quieter boat experience than we would on a motorboat—and that we’d only use the motor (which wasn’t too loud) when we really needed to.

Far from the average tour guide running through a memorized script, once we were underway, he filled the ride with stories about the harbor while answering some of our ridiculously niche history questions with confidence. He even pulled out a pair of hilariously goofy motion-sickness goggles that looked like something from a science experience. (In all fairness, I do think they helped.)

About 10 minutes in, we slipped beneath the Brooklyn Bridge, its stone towers rising above us and its cables stretching overhead, then continued past FiDi’s glass skyline, Governors Island, and toward the Statue of Liberty and Ellis Island. I remember thinking how everything felt slightly rearranged from the water—the buildings looked taller, the bridges more dramatic, and the landmarks I’d seen countless times as a native New Yorker suddenly had new details.

Creating Our Own Floating Picnic

We watched the bright orange Staten Island Ferry pull into the downtown terminal, waved at passing boats, and spotted seabirds skimming just above the rippled waves. At one point, we passed some of the larger sightseeing boats packed with passengers, and as people waved at our tinier, more exclusive vessel, one of my friends laughed and said, “I feel famous.” It was a joke, of course, but it captured exactly what made the afternoon special: While the bigger boats were rushing passengers from one landmark to the next, we were simply sailing, with lots of room (and serenity, thanks to no motor sounds) to actually take it all in.

One of my favorite parts of the experience was being able to make the boat our own for two-and-a-half hours. Brooklyn Sail allows you to bring food on board, so naturally, I stopped at Eataly on the way over and picked up some herb butter, a baguette, and pasta salads to share. One friend brought the wine, another showed up with an entire charcuterie board and fruit trays. It was like our own floating picnic. Ian always has cups and a cooler onboard, so we left a few essentials in there to chill.

I did make one classic mistake: I forgot my anti-nausea medication at home. If you’re someone who is prone to motion sickness, learn from me and know it’s best to come prepared. But if you’re not, thankfully, Ian will be ready. He handed me remedy wristbands, offered Dramamine, and even pulled out a pair of hilariously goofy motion-sickness goggles that looked like something from a science experience. (In all fairness, I do think they helped.)

Conclusion: An Unforgettable Experience with Brooklyn Sail

As we pulled back into Pier 5 as the sun started to dip, everyone slightly sun-tired but noticeably way more rejuvenated than when we arrived. We grabbed a spot at one of the sprawling picnic tables beside the marina and finished the snacks we had been too distracted by the views (and the wind!) to fully enjoy earlier. Before we could even leave the dock, though, Ian came running after me to make sure I didn’t forget the herb butter I had tucked away in the cooler.

“What a 10/10 captain,” we all agreed. The darling Enchantress, docked in the harbor, was a sight to behold, and I couldn’t help but feel grateful for the experience. Brooklyn Sail’s story is almost as fun as the sail itself. After moving to New York after college in 2009, Ian started looking for a creative way to avoid paying rent, and landed on the idea of living aboard a sailboat. The problem was finding a place to keep one—the marina waitlists were long, and winters on a New York boat were less than appealing.

Instead, he bought a used sailboat and spent two winters living on it in the Bahamas, working remotely and anchoring in different places. He eventually sold the boat years later for the same price he paid. When Brooklyn opened a new marina, he saw the opportunity to bring that same sense of adventure closer to home and opened Brooklyn Sail in 2017. His brother Andrew later joined him as a captain.

About the Author: As a native New Yorker, I’ve had the privilege of experiencing the city’s vibrant culture and breathtaking views from various angles. However, nothing compares to the sense of wonder and awe that I felt during an evening sailing adventure with Brooklyn Sail. I’m always on the lookout for unique experiences that showcase the city’s hidden gems, and Brooklyn Sail’s sailing adventure is definitely one to add to your bucket list.