Tailwind Air

Tailwind Air is a veteran-owned business motivated by a passion for aviation and urban mobility. Founded in 2012, Tailwind Air is experienced in amphibious seaplane operations and committed to delivering time savings to customers by utilizing waterways and smaller airports closer to urban cores. In addition to seaplanes, Tailwind Air operates, charters, and maintains a fleet of over 15 jet and turboprop aircraft based out of Westchester Airport, NY, and Bridgeport, CT. Tailwind Air is an FAA and DOT-licensed direct air carrier with certificate number XORA037U.

Tailwind Air operates a young fleet of modern, safe, and reliable Cessna Caravan Amphibian seaplanes. With over 2,500 built, Caravans are used by regional airlines throughout the United States and the world. Their planes can touch down on water or land, have two pilots, comfortable seating, and crisp air-conditioning, and provide an incredible view.

Tailwind’s seaplanes are the fastest way in and out of urban centers. Passengers fly over the traffic on well-timed scheduled shuttles to Boston Harbor, Bridgeport, Nantucket, Provincetown, CT, or one of our three destinations in the Hamptons. There is also the option of chartering one of their seaplanes to Nantucket, Martha’s Vineyard, Block Island, Fishers Island, Upstate New York, New Hampshire, Vermont, Maine, Virginia, or anywhere else in between.

Tailwind Air is proud to relaunch the season’s nonstop weekday flights at peak hours to and from Manhattan and Boston Harbor, which present exclusive time savings over all other modes of transportation at a reasonable price premium. This seaplane service combines the accessibility of a train with the speed of a flight.

Because Tailwind’s seaplanes take off and land on waterways, this exclusive service is a game changer for travelers between eastern seaboard cities. Bypassing the city’s congestion, the airline is the first to fly directly into Boston Harbor from Manhattan.

Tailwind Air is a pioneer in regional urban mobility while using long-proven technology. Tailwind Air cuts travel times by 40% to 60%, and their premium service reduces aggravation and opens up half-day business trips. Due to the eight-passenger capacity of the seaplanes and the small, efficient facilities, guests can check in as little as ten minutes before departure.

While Tailwind Air’s seaplane fleet is young, less than five years on average, seaplane travel certainly is not. The Manhattan Skyport opened in 1936 and has been hosting popular seaplane travel for decades. For nearly 100 years, seaplane operations have been part of the core transportation landscape of maritime cities such as Seattle, Miami, and Vancouver.

Tailwind’s website, flytailwind.com, provides the complete schedule of all flights operated by Tailwind Air, including their Boston Harbor–Manhattan flights. Tickets can be purchased on the website, by phone, and through local travel agencies via a codeshare partnership with Southern Airways Express.

For travel agents interested in partnerships, Tailwind Air offers generous commission rates. Tailwind Air also offers discounted prepaid commuter books of 10, 20, and 50 tickets for passengers, which can be shared with colleagues, friends, and family and save 35% or more off last-minute fares. Corporate rates are also available.

The onboard experience includes up to 36″ of seat pitch and leather seats, all with aisle and window access. In addition, each aircraft are fully air-conditioned.

The on-the-ground experience is unparalleled and includes weather-protected boat transfer in Boston Harbor. Tailwind Air has passenger lounges at Fan Pier Marina and New York Skyports seaplane base, offering complimentary water and select beverages, light snacks, and nearby restrooms.