It was an abnormally warm February afternoon when we traveled to the Atlantic Basin harbor in Brooklyn where a group of sailors were pounding and painting on the Clipper City. This could sound like the start of a noir detective story on the old waterfront, only this was happening in 2013.  We were checking out Manhattan By Sail, a company that specializes in boating tours of the New York Harbor, where they have been continuing a tradition of sailing the New York harbor that dates back to when Manhattan was first being called New Amsterdam. Untapped Cities took a tour of the boat in the off season to get a look at their connection to the working waterfront.


Our guide for the day was Tom Berton, owner and operator of Manhattan by Sail. Berton is a life long New Yorker. He didn’t intend to be a sailor, but caught the bug after stumbling upon Captain Nick Van Nes loading cargo on a sailboat while rollerblading downtown. Van Nes operated the Petrel out of Battery Park after returning from Vietnam, and Berton is sure that he did not even have permits when he was tying up to the crumbling piers of 1970s Manhattan. Van Nes was a real pioneer of pleasure boating in New York City.  Berton volunteered for him and entered this special enclave of New York City sailors, a group that could quickly escape the city without having to take a train or car.  He loved getting out on the ocean, and spending nights sleeping on the boat to make sure thieves didn’t strip it.

After a career in real estate and retail that took him from a national park in Canada to cities in Japan, Berton came (full sail!) back to Manhattan. In retirement at Martha’s Vineyard, Berton gathered investors and got his own boat. They were able to acquire the 82 foot Shearwater, a Gatbsy-era pleasure schooner that was built in 1929 at Boothbay Harbor, Maine.  This boat is a real gem, traditionally crafted and built entirely out of natural hardwoods. The boat was designed by Theodore D. Wells, a New York native who, before working for the Naval department, worked at a firm designing boats here in the city.

After starting off as a pleasure boat, Shearwater was conscripted in to military service during World War II to patrol the Chesapeake Bay. In the 1970s it was owned by the University of Pennslyvannia for scientific research, and after trading hands again, circumnavigated the globe for over two years in the early ’80s. Shearwater was unfortunately wrapped for protection for the winter, but the photo shows the beautiful curves and scale of the ship.


In order to turn Manhattan by Sail into a full time company, Berton also purchased the Clipper City in 2009.  A beautiful steel hulled yacht, Clipper City was rebuilt in 1984 from plans that were taken out from the Smithosian. The original boat was built in Wisconsin in 1890, and later became well known for hauling lumber. For two decades the ship rusted in Baltimore, but Berton and crew were able to purchase it and give the proper repairs to return it to service. The larger Clipper City allowed Berton and his crew to really turn Manhattan by Sail into a business.  Its mast is so tall that it just squeezes under the Brooklyn Bridge at high tide. The Shearwater takes out about 48 people plus the crew, while Clipper City can take up to 150, “very comfortably” Berton stresses. Combined, the ships take between 60,000 to 70,000 people out on the water each season.


Sailing has long been a part of the New York Harbor, but it can still be a dangerous job for those involved. Berton was moored in Battery Park on September 11th 2001, when Manhattan by Sail was still a new business, and had full view of the towers as the events unfolded. “The worst day of my life,” he explained.  They had also just tied up at Southstreet Seaport when it caught fire this past July. They had to toss people back on the boat and untie to get off the harbor for fear of it burning down. If the wind had been blowing in another direction, there could have been serious injuries. This has not deterred the captains or crew of Manhattan by Sail, and they still believe sailing is the best way to temporarily escape from the city.

We were able to explore Clipper City, and it was in the midst of heavy work by the crew due to the wear and tear it receives living on the harbor. The hull had just been patched up at Caddell Dry Dock in Staten Island, and necessary repairs to the topside were being done. The real wood creaks as it rises up and down out of the water. We also explored the interior of the boat, which is slowly being transitioned from predominantly residential use to something that can support the tour business.



Manhattan by Sail employs about 50 people, everything from marketers and managers to full time sailors. When not on the ship, many of these employees embark on other projects like music, cooking, acting and manufacturing. One summer, Laura Dekker, the youngest girl to circumnavigate the globe on a sail boat, worked as a deck hand. Another employee, Chris, also works a foundry in Brooklyn. With all these collective experiences, the Clipper City’s sailors can talk to patrons about any number of topics happening around New York City, in addition to showing the intricacies of sailing and the surprisingly aggressive behavior of the New York Harbor’s tidal currents.



Originally Manhattan by Sail catered only to New Yorkers, and prior to 2008, a most of the business was corporate charters and private parties, but the recession has dropped this type of lucrative business. To continue to attract smaller groups of New Yorkers, Manhattan by Sail has evolved.

The first Jazz on the Water sprung out of a chance meeting.  A few years ago Berton ran in to an old family friend Joe Cohn at Lincoln Center, who was playing with Wynton Marsalis. Recognizing him afterwards, he approached him with the idea of playing on his boat. “We now have a tight quartet that plays really good stuff.” And Berton knows jazz, as his father was a longtime Jazz critic for the New York Times.

In addition, Berton has also conceived Manhattan by Sail trips like the Lobster and Beer sail,  the gay-friendly Top or Tail sail, and a Distilled In Brooklyn one featuring Booklyn made spirits. For food they usually pull in local caterers like Radish and Luke’s Lobster.  The combination of getting people out in the harbor and pairing up with our favorite local businesses makes us very happy at Untapped Cities.

This cat just wanders on the ship whenever he feels like it
This cat just wanders on the ship whenever he feels like it

Getting out and exploring the boat during the its off season was interesting to see the amount of work that has to be done to prepare before the upcoming season.  This trip was also sort of nostalgic for us because just across the basin is the Brooklyn Cruise Terminal, the subject of my first article for Untapped.  It is interesting to see the inside mechanics of the working waterfront, and to meet people who don’t quite fit in the office towers of Midtown but are perfectly at home along the industrial fringes of the waterfront. With Manhattan by Sail, you can get out and experience the harbor in a traditional way with a modern twist.  Tours start April 26th, come out and you will hopefully see some of the Untapped writers there.