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Chesto Means Business

Cape Air on course for seaplane takeoff in Boston

Cape Air officials said they were happy with their first Boston Harbor test flight for a seaplane service they want to bring to the South Boston waterfront.Cape Air

Dan Wolf needed to get his hands on an amphibious aircraft before he could fulfill his yearslong quest to bring seaplane service back to Boston Harbor.

Now, the chief executive of Cape Air has an entire squadron.

The Hyannis-based airline disclosed this week that it had acquired the assets of Shoreline Aviation, a Connecticut company that has billed itself as the biggest seaplane operator on the East Coast. Shoreline owns three seaplanes and leases seven more, primarily for chartered jaunts between Manhattan and the wealthy seaside playgrounds of East Hampton, Montauk, and Shelter Island.

Meanwhile, Cape Air bought its own amphibious Cessna Grand Caravan EX last month, with room for nine passengers. A second order is planned. All told, Wolf expects to have a dozen seaplanes at his disposal this year.


For Wolf, though, acquiring Shoreline isn’t just about aircraft. It’s also about experience: Shoreline’s crew of 14 seaplane pilots provide valuable skills as Wolf is taxiing his own venture for takeoff. Maintaining seaplanes requires unique technical expertise, and flying in and out of New York’s busy East River is good prep for bustling Boston Harbor. (Cape Air’s previous experience in the seaplane business was relatively brief, a stint flying out of Miami that lasted about two years.)

Cape Air has recently acquired this Cessna that it plans to use in seaplane flights between Boston and New York. Cape Air

Wolf first learned to fly a seaplane at the Goodspeed Airport along the Connecticut River, while going to school at nearby Wesleyan University. That was nearly 40 years ago, but there’s a connection to this latest deal. Shoreline Aviation was run by John Kelly, who taught Wolf during his college years. They obviously stayed in touch: Cape Air has used Shoreline planes during its Boston Harbor test runs.

As a former state senator, Wolf knows a thing or two about lining up votes. He says the Cape Air team has had more than 100 meetings with community members and civic leaders in Boston about the seaplane service, dating back to the Menino administration. The Federal Aviation Administration gave its crucial green light last fall.


Wolf plans to start with chartered trips, possibly to Cape Cod and the Islands. He hopes to get regularly scheduled service running out of Boston Harbor, near Logan Airport, as soon as July.

The focus would be on business travelers, the people who need to get to and from New York in a hurry. Flights between Boston and the East 23rd Street dock in Manhattan would take just over an hour, bypassing all the maddening bridge and tunnel traffic that separates both cities’ airports from their main business districts. Wolf hopes to charge prices that would be competitive with the walk-up prices for shuttle flights out of Logan (roughly $400 today, one-way). Wolf plans to start with two daily flights from Boston, and then expand to four in the fall once Cape Air acquires that twelfth plane. A typical season would stretch from March to December.

The ramp for sea planes at the Boston Airport in 1935. Boston Globe Archive

But one more hurdle remains. And it’s not insignificant. Wolf still needs a place to dock in Boston. Rival Tailwind ran into a similar issue; it currently advertises its New York flights as landing at Logan’s general aviation terminal, not on the water.

Wolf’s hunt for real estate continues, with a focus on the booming South Boston waterfront. Of course, this happens to be one of the hottest markets in the country. Even dock space is in short supply.


Many of Wolf’s employees spend much of their time airborne, but he still needs to grapple with the same headache that vexes other CEOs in town: the high cost of real estate. Wolf has figured out how to pay for the planes. And now he might want to sock away a few dollars for that dock.

Jon Chesto can be reached at Follow him on Twitter @jonchesto.