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. Seeing the Statue of Liberty so close was a moment that really stayed with me: As we slowly approached from the harbor, the boat placed us close enough to take in the shape of her against the open water.
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. A quick tip: It does get windy out on the harbor, so I’d avoid bringing lightweight plastic containers or anything that could easily blow away. The cooler is also stocked with drinks available for purchase, including hard seltzers, ciders, beer, wine (white and rosé), and Champagne, should you not want to bring your own.