On a warm July afternoon I met four close friends at Brooklyn Bridge Park’s Pier 5 for one of my favorite New York outings: a private evening sail with Brooklyn Sail. The waterfront scene felt quintessentially Brooklyn—soccer fields and community projects along the marina, sailboats bobbing in their slips, and the Manhattan skyline spread across the water. It was a sharp, delightful contrast to the Financial District I’d left earlier; the subway had taken 20 minutes, but the mood felt like another world.
I found Brooklyn Sail on Airbnb Experiences while searching for something different from the usual dinner or rooftop plan. Availability was good a couple of weeks out, and the reviews were full of detailed stories rather than empty praise, so I booked a private sail for our group. We arrived with picnic bags in hand at 5 p.m., and Captain Ian—one of the brothers who started the company—greeted us punctually. After a concise but thorough safety briefing he helped us aboard the Enchantress, a classic sailboat with warm wood interiors, deep navy cushions, and a comfortable cockpit. There’s a small onboard bathroom and enough room to move, stretch, and enjoy the views without frills.
We stowed our things, kicked off our shoes, and Ian cast off. We chose to stay on deck—too warm to go below—and took turns lounging near the mast or on the cushioned stern as the skyline shifted behind us. The vibe felt very personal from the start: Ian’s easygoing presence and clear love of sailing put everyone at ease. He explained that the boat would be quieter than a motorboat and that the motor would only be used when necessary. Rather than reciting a rote script, he answered our oddball history questions and told stories about the harbor along the way.
About ten minutes after leaving the marina we slipped beneath the Brooklyn Bridge, with its towers looming above and cables overhead. We then cruised past FiDi’s glass towers, around Governors Island, and out toward the Statue of Liberty and Ellis Island. Seeing Lady Liberty close up from the water was unexpectedly moving—the perspective from a sailboat makes familiar landmarks feel new: buildings seem taller, bridges more dramatic, and details jump out that you don’t notice from the sidewalk.
The sail felt leisurely and unhurried. We waved at passing ferries, watched seabirds skim the waves, and passed larger sightseeing vessels full of people. Because our boat was small and quieter, we had space to actually talk and take in the view, which made the outing feel intimate. One friend joked about feeling famous when people on the big tour boats waved at us; it was a silly line, but it captured what made the trip special.
Brooklyn Sail lets guests bring food, so I swung by Eataly on the way to grab herb butter, a baguette, and some salads. Others brought wine, charcuterie, and fruit—our own floating picnic. The crew provides cups and a cooler, and the boat’s cooler is also stocked with drinks for purchase (hard seltzers, beer, cider, white and rosé wines, and Champagne), in case you don’t want to carry everything. Tip: it gets windy on the harbor, so avoid loose lightweight containers that can blow away.
I made one rookie mistake: I forgot my anti-nausea medication. If you’re prone to motion sickness, bring whatever works for you. Ian offered remedy wristbands, Dramamine, and even motion-sickness goggles that looked hilariously futuristic; they probably helped. The captains are prepared and attentive, and the overall pace is gentle, but it’s smart to come ready.
The sail lasted about two and a half hours and felt like the perfect length: long enough to relax into the experience and see major landmarks, short enough to keep energy high. We returned to Pier 5 as the sun began to dip, slightly sun-tired and noticeably refreshed. Ian even chased me down on the dock to make sure I hadn’t left behind the herb butter—small touches like that made the trip feel cared for.
A bit about Brooklyn Sail: Ian started living aboard boats after moving to New York, spending winters living on a sailboat in the Bahamas before returning to open Brooklyn Sail in 2017 when a new marina became available. His brother Andrew later joined as a captain, and the business grew into a family-run operation offering a handful of sailing experiences.
How to book and what to expect: The Enchantress sails seven days a week with departures at roughly 9:00 a.m., 11:30 a.m., 2:30 p.m., 5:00 p.m., and 7:30 p.m. Options include private sails (reserve the whole boat for up to six guests), individual-seat sightseeing sails (priced per person and paired with other passengers), and City Lights sails for night cruises. Sightseeing sails run mostly during the day with occasional sunset slots; evenings and weekends fill fastest. The season typically runs from early May through late October, weather permitting—booking about two weeks in advance is a good rule of thumb.
Splitting the private-sail cost among friends made it feel very accessible. If you book individual seats, smaller parties will be combined until the boat has six passengers; if a sail doesn’t fill, the company may contact you 24–48 hours ahead to reschedule or refund.
If you’re a local or a visitor who wants a different way to see the city, a Brooklyn Sail trip is an easy, low-key way to romanticize the harbor—even on a weekday. Quiet sails, personal attention from the captain, room to chat and picnic, and up-close views of iconic landmarks make it one of the best ways I’ve seen New York from the water.
