This summer has seen its share of delayed and canceled flights, crowded airports and longer-than-normal TSA lines. For affluent leisure and business travelers in the Northeast, however, flying on Tailwind Air to destinations like New York City, Boston, Provincetown and the Hamptons has never been easier.
For passengers departing New York for Boston, Tailwind Air offers scheduled seaplane flights from the New York Skyports Seaplane Base, located where East 23rd Street meets the East River. It is so conveniently located many passengers can simply walk there from their Manhattan offices or apartments.

© Courtesy of Tailwind
After checking in at the Tailwind lounge, where passengers can arrive 15–20 minutes before flight time, they are escorted to the end of the pier where an amphibious eight-passenger (plus two pilots) Cessna Caravan aircraft awaits. Boarding is quick and baggage (limited to 20 pounds per person) is easily stowed in the back.
The pilots use the East River as their runway, and within a few minutes after boarding, you are flying above the river, parallel to Manhattan’s skyscrapers, on the way to a soft landing in Boston Harbor near Fan Pier Marina or The Marina at Rowes Wharf, about 60 minutes later.

Institute of Contemporary Art, Boston © Chuck Choi
Tailwind Air uses amphibious aircraft, meaning they can land on water or airport runway. The company currently awaits approval for a Washington, D.C., route to begin after Labor Day.
Here are the destinations currently served by Tailwind Air:
Water: Manhattan, Boston Harbor, Sag Harbor, Shelter Island.
Land: East Hampton Airport (HTO/JPX), Montauk Airport (MTP), Provincetown Airport (PVC), Plymouth Airport (PYM), Bridgeport Airport (BDR)
Tailwind’s seaplane flights are restricted to daylight hours (about 6 a.m–7 p.m.) from mid-spring to mid-fall (a longer season applies to New York and Boston). Aircraft seating is quite comfortable, with four passenger seats on each side, plenty of legroom and air conditioning. Additionally, flying at about 6,000 feet provides guests with a close-up look at the terrain below.

© Boston Harbor Hotel
The deluxe Boston Harbor Hotel, located directly at The Marina on Rowes Wharf, is conveniently located for Tailwind’s arriving Boston passengers. All 232 guestrooms offer harbor or city views, and fresh fish and seafood is available at the on-site Rowes Wharf Sea Grille. A spacious fitness center provides excellent equipment and an indoor pool. Boston’s financial district and many historic attractions are within walking distance, including the modern Diller Scofidio + Renfro-designed Institute of Contemporary Art, located just a five-minute walk away at Fan Pier Marina.
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