Getting a sailor's-eye view of Manhattan

Eight of us stood on a dock opposite Manhattan on the East River one summery Sunday morning waiting to board a 26-foot sailboat that didn't look much bigger than a dinghy.

Ranging in age from 30 to 60, we had all signed up for a one-day Outward Bound course, "Circumnavigating Manhattan by Pulling Boat."


I'd chosen this adventure because while I'd seen parts of the world's most populated island by ferryboat, speedboat, yacht and even kayak, I'd never gone around the entire perimeter of Manhattan by boat.

Trevor Harris, one of the two Outward Bound guides, introduced himself and fellow guide Paul Matylas, and said, "Outward Bound is the moment a ship leaves safe harbor for unknown dangers and adventures on the open sea."


He handed us life jackets and added, "In Outward Bound, there are no passengers, just crew. Paul and I are only here because the Coast Guard requires two guides. Once we teach you, you're going to call all the shots."

"This is a Monomoy sailboat," Paul explained. "It's called a pulling boat because when the wind dies down, the crew has to 'pull' the boat with oars."

There were a few groans as Paul continued: "We normally use the boat as an outdoor classroom for New York City Outward Bound school kids. You're just going out for the day, but the kids go out for two weeks and sleep on the boat."

"Where?" someone asked.

"We lay the oars across and spread a tarp, and they sleep on top."

"All of them?" the same person asked.

"It's a good learning experience," Paul said. "They learn to live and work together in this very small space."

"We'll head up the Harlem River, shoot out into the Hudson and catch the ebb current," Trevor said. "If we get to the Battery [in Lower Manhattan] too early, we'll wait until the tide changes before turning back in the East River. OK, grab those oars and pay attention, because it's easy to get smacked in the head. Let's board."


Four people volunteered to row; one was designated captain, one navigator and two of us were lookouts. Trevor said we'd rotate often so everyone would have the chance to try each position.

I was glad I didn't have to start as captain -- lookout seemed an excellent position. I had time to observe Manhattan from the other side of the river. The Empire State Building, United Nations and Chrysler buildings looked completely different from this perspective -- taller and more imposing.

From here, all the skyscrapers looked like pencils of different heights and widths, stacked side by side, their points sticking straight up in the air.

After explaining how important it was for the rowers to stay in unison, Trevor said, "Come to oars," and the rowers gripped the handles and sliced their wooden oars through the water. I sat in the bow inhaling the salt air, listening to the oars splash and feeling the sun warm my face. It wasn't long before we were parallel to the U.N. building.

Soon we were nearing the ivy-covered townhouses of Sutton Place, where I often come to sit in the pocket-sized parks, but I'd never seen this oasis of flowering gardens and velvety green lawns because they are only visible from the river.

We rowed by the southern tip of Roosevelt Island, where ruins of what I thought was an estate turned out to be those of a former tuberculosis sanitarium. Originally called Welfare Island, there had also been a jail where Mae West was confined for eight days after what authorities called a "lewd" performance.


Just before the Queensboro Bridge, we switched positions and I became a rower. The oar felt like a steel girder, and it took a while before we synchronized our strokes and stopped bumping into each others' oars.

I looked up at the Queensboro Bridge I knew better as the 59th Street Bridge. I'd driven over it many times, often stuck in traffic.

By the time we arrived beneath the Triborough Bridge, my arms were aching. The Triborough is actually three bridges that connect the boroughs of Manhattan, Queens and the Bronx, and over which some 200,000 vehicles pass daily.

The East River flows into the Harlem River at the northern tip of Manhattan, but before you get to the Hudson, you go under eight bridges.

The most beautiful bridge, I thought, was High Bridge, which has 15 arches and looks like a Roman aqueduct. The bridge has a pedestrian walkway 135 feet above the river, but it was closed in 1970 when a pedestrian threw a rock onto a sightseeing boat below, killing a tourist.

It was time to switch, so I handed off my oar and took my place as captain. Before long, we entered the Hudson, with the George Washington Bridge in the distance and a huge Circle Line boat bearing toward us.


"What do I do?" I asked, trying to keep the panic out of my voice.

"We have the right of way," Trevor said calmly.

"Yes, but what if he can't see us?"

Trevor just smiled. The Circle Line tour boat gave us wide berth, leaving a large wake in its path.

Ahead of us was every type of watercraft, making the river as congested as the city during rush hour. A motorboat passed, then four personal watercraft followed by a three-masted sailboat motoring up the river. A speedboat thundered by.

We passed the blue "C" painted on a rock near Columbia University's athletic fields. Further down on shore was a public park where a group of boys about 8 years old gestured and screamed. We couldn't hear them, but we waved. They pointed at something in the river -- a soccer ball bobbing in the distance.


"Can we retrieve it?" I asked Paul.

"The currents are really strong here, and if we [are] going for it, we'll have to row hard, but you're the captain, so you make the choice," he said.

"Let's go for it," I replied, glad I wasn't rowing.

We scooped up the ball and headed toward the kids, but there was no place to land. Paul said we would land at the nearby Dyckman marina, our lunch stop.

But then there was more commotion from shore, this time, from a group of teenagers whose soccer ball was also swimming in the Hudson. The rowers were exhausted, but we went for it, and finally pulled into the marina with the soccer balls, which we handed off to two grateful recipients.

After lunch, there was enough wind to sail. I was back to my favorite position -- lookout -- which meant I could sprawl on the bow, soak up the sun and watch the George Washington Bridge loom closer and closer until we were right under it.


On the bank was a red lighthouse, built in 1920 and made popular by the children's book, The Little Red Lighthouse and the Great Gray Bridge. When the bridge was built, the lighthouse was set for demolition, but millions of children who loved the lighthouse spoke out, saving it from destruction.

There was more river traffic as we headed south: Circle Line boats, private yachts, sailboats and a yellow-and-black-checkered New York water taxi. The Chelsea Screamer, a high-speed hydrofoil, whizzed past, followed by a large rental party boat blaring salsa music.

Eventually, the traffic dispersed, and the only sound was the sail flapping and the water lapping at the hull. We sailed past Riverside Park and the 79th Street Boat Basin. Further down was a docked barge where hundreds of rusted subway cars were stacked on top of each other.

We were passing the aircraft carrier Intrepid as a Norwegian cruise ship four city blocks long pulled out of its berth and headed toward the open water. At least five stories up on the top deck, passengers waved, and we waved back.

The southern tip of Manhattan was eerie with the Twin Towers missing, but there was no time to think about that because there was a parade of boats all heading north: pleasure craft, party yachts, speedboats, sailboats, kayaks and even a canoe.

"Be glad it's Sunday," Paul said. "During the week, you have all this plus every commuter and ferry boat."


I've walked across the Brooklyn Bridge but never approached it under full sail. We passed beneath the Manhattan and Williamsburg bridges, and then the wind died down, so we furled the sail and rowed.

I knew our journey was almost over because the U.N. building was in the distance -- a silver slab gleaming in the late-afternoon sun. Finally, we pulled into Long Island City, 10 hours from the time we'd started out. I didn't feel tired -- I felt exhilarated.

When you go

For information about a one-day Outward Bound circumnavigation of Manhattan in September, along with other Outward Bound programs, call 845-424-4000 or visit the Web site

Other ways to see Manhattan by water:

Circle Line Sightseeing Cruises



Three-hour full island cruise includes the entire 35 miles of Manhattan Island and a close-up of the Statue of Liberty.

Beast Speed Boat



Speed around New York Harbor at 45 mph.

NY Waterway


Two-hour full island Manhattan cruise or one-hour Lower Harbor cruise.

World Yacht



Dining cruises aboard a yacht also include dancing to live music and the city skyline at night. Brunch cruise also available.

New York Kayak Co.



Offers tours to advanced paddlers as well as classes on the Hudson River.

Manhattan Kayak Co.


Offers more than 30 local tours.

Downtown Boathouse



The all-volunteer group offers free kayaking on the Hudson to anyone who shows up and can swim. Three-hour guided trips available on weekends and holiday mornings.