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2021 Complete flight schedule

Total One Way Travel Time: Midtown to Midtown: NYC to Boston

Tailwind Air opens up half day work trips to/from Boston and New York and provides a valuable alternative to existing options

Seaplane Destination Map

Charter Range Map

Our Fleet

CARAVAN EX

8 seats
Range: ~400 miles

2021 Complete Flight Schedule

to/from Boston Harbor

August 21 – September 30th, 2021

NYS → BNH

From Manhattan (NYS) OUTBOUND to Boston Harbor (BNH)

MondayTuesdayWednesdayThursday Friday
8:00 a.m.8:00 a.m.8:00 a.m.8:00 a.m.8:00 a.m.
9:30 a.m.9:30 a.m.9:30 a.m.9:30 a.m.9:30 a.m. (Eff. Sept 10)
2:30 p.m.2:30 p.m.2:30 p.m.2:30 p.m.2:30 p.m.
4:45 p.m.4:45 p.m.4:45 p.m.4:45 p.m.4:45 p.m. (Eff. Sept 10)

BNH → NYS

From Boston Harbor (BNH) OUTBOUND to Manhattan (NYS)

MondayTuesdayWednesdayThursday Friday
7:00 a.m.7:00 a.m.7:00 a.m.7:00 a.m.7:00 a.m.
10:05 a.m.10:05 a.m.10:05 a.m.10:05 a.m.10:05 a.m.
2:10 p.m.2:10 p.m.2:10 p.m.2:10 p.m.
5:20 p.m.5:20 p.m.5:20 p.m.5:20 p.m.5:20 p.m.

TO/FROM EAST HAMPTON ​

May 20- September 28th, 2021

NYS → HTO

From Manhattan (NYS) OUTBOUND to East Hampton (HTO)

WednesdayThursday Friday
3:30 p.m.3:00 p.m.
5:30 p.m.5:45 p.m.5:15 p.m.

HTO → NYS

East Hampton (HTO) INBOUND to From Manhattan (NYS

Sunday Monday
7:00 a.m.
3:45 p.m.9:30 a.m.
6:15 p.m.

TO/FROM SHELTER ISLAND

May 20- September 28th, 2021

NYS → DXE

From Manhattan (NYS) OUTBOUND to Shelter Island (DXE)

WednesdayThursday Friday
3:15 p.m.2:45 p.m.
5:30 p.m.6:00 p.m.5:30 p.m.

DXE → NYS

Shelter Island (DXE) INBOUND to From Manhattan (NYS

Sunday Monday
7:15 a.m.
3:30 p.m.9:45 a.m.
6:00 p.m.

TO/FROM MONTAUK

May 20- September 28th, 2021

NYS → MTP

From Manhattan (NYS) OUTBOUND to Montauk (MTP)

WednesdayThursday Friday
5:30 p.m.6:00 p.m.5:30 p.m.

MTP → NYS

From Montauk (MTP) OUTBOUND to Manhattan (NYS)

Sunday Monday
3:15 p.m.

Discounts

SAVE UP TO 35%

And get access to all of our inventory when you purchase our prepaid commuter books.

Discounted charters

Tailwind offers discounted private charter options for commuter book holders.

Corporate Rates

Great corporate rates are also available! Contact us here for more info

Commuter Ticket Book Membership

NYS-BNH
10 Pack Commuter Book Manhattan to/from Boston $5,950 
20 Pack Commuter Book Manhattan to/from Boston $11,000 
50 Pack Commuter Book Manhattan to/from Boston $26,250

NYS-HTO
10 Pack Commuter Book Manhattan to/from East Hampton $7,018
20 Pack Commuter Book Manhattan to/from East Hampton $13,498

NYS-MTP
10 Pack Commuter Book Manhattan to/from Montauk Airport $8,093
20 Pack Commuter Book Manhattan to/from Montauk Airport $15,648

NYS-SH1
10 Pack Commuter Book Manhattan to/from Shelter Island $6,490
20 Pack Commuter Book Manhattan to/from Shelter Island $12,480

All (Superbook)
10 Pack SUPERBOOK $7,297
20 Pack SUPERBOOK $14,057
50 Pack SUPERBOOK $33,530

Holiday Schedule 2021

Sunday May 30 – No Flights
Monday May 31 – Sunday Schedule
Tuesday June 1 – Monday Schedule
Sunday July 4 – No Flights
Monday July 5 – Sunday Schedule
Tuesday July 6 – Monday Schedule
Sunday Sept 5 – No Flights
Monday Sept 6 — Sunday Schedule
Tuesday Sept 7 — Monday Schedule

Covid-19 Statement

Tailwind Air is taking active steps in light of the COVID 19 virus to ensure that our operations remain safe, reliable, and clean.  We follow the guidance of the CDC and FAA and have active steps in place to reduce the risk of the virus. These include but are not limited to:

  • Enhanced cleaning, pre and post flight checks, and other precautions along with a detailed checklist that is completed before and after each flight. 
  • Only single use soft goods (sodas, cups, etc) will be used until further notice.
  • We strongly encourage passengers to bring their own masks and gloves.
  • Flight crews and staff will wear masks and gloves to the extent they do not interfere with flight safety, including during all loading, unloading, and check-in activity.
  • Crews are equipped with thermal temperature scanners and will deny boarding to anyone presenting an elevated body temperature.

About Tailwind

Tailwind is a veteran-owned FAA part 135 licensed and insured operator/manager of aircraft based in Rye Brook, NY (HPN). We have owned, managed and flown scheduled and charter passenger seaplane service into Manhattan’s East River street for over 6 years.  We also own and manage a fleet of regional turbo prop and jet aircraft available for charter. Find out more at www.flytailwind.com (please be patient, updates reflecting our expanded service are in progress).

About Our Seaplanes

Tailwind operates a fleet of advanced Cessna Caravan amphibious seaplanes seating 8 Passengers and always using 2 pilot crews. We conform with and often exceed all applicable FAA standards. In addition, we provide real time flight tracking.

Contact Us

Commuter Memberships/Books:   Call 212-328-9145 or Contact Reservations@flytailwind.com
General Inquiries:  212-328-9145 or info@flytailwind.com
Charter:  212-328- 9145 or charter@flytailwind.com
www.flytailwind.com

FAQ

We hope this FAQ will help answer your questions about Tailwind Air – if you need more information, please contact us at info@flytailwind.com

From Manhattan, we have scheduled service to Boston Harbor, Bridgeport, East Hampton, Shelter Island, and Montauk.  For details, see our schedule.

NOW OFFERING OUR SHUTTLE SERVICE FROM BOSTON TO MANHATTAN

On-demand seaplane charter is available to the Hamptons, Montauk, Martha’s Vineyard, Nantucket, Albany, Toronto, Washington, Baltimore, Chesapeake Bay, LBI, Bar Harbor, upper Vermont and New Hampshire, Lake George, you name it! For more see https://www.flytailwind.com/flights/

Tailwind Air also directly operates a complete range of charter aircraft from intercontinental Falcon 900 14 seat jets to fast 5 passenger regional turboprops. For more information see https://www.flytailwind.com/charters-new/

For our scheduled flights, you can book a flight via our website or through our code-share partner Southern Airways at www.iflysouthern.com . Flights are also available on many online travel sites and through your local travel agent. You can also call us at 212-328-9145. We offer discounted commuter books of 10, 20 and 50 tickets and extra perks for those who travel frequently. These can be purchased via our website or by calling 212-328-9145.  Charter inquiries should be directed to charter@flytailwind.com

Southern Airways is a code-share partner of ours. Some tickets may be issued and sold through Southern Airways. No matter how you purchase your seats, all flights are operated by Tailwind Air. Welcome aboard!

Ticket prices vary, but one way fares begin at less than $200 for select Bridgeport flights, $350 for select Boston flights, and $695 for select Hamptons destinations. Further discounts are available through multi-ticket commuter packs. Commuter books may be purchased on our website at flytailwind.com, by emailing info@flytailwind.com, or by calling 212-328-9145

Yes.  A standard sized airline carry-on of 20 lbs. is included with your fare on Tailwind Scheduled service.  For ANY larger or heavier items, including golf bags and strollers, please contact us to make special arrangements.  Please note that we do not have the capacity to check luggage, and all luggage will be securely stored in-cabin or securely in in the aircraft float lockers.

Terminal Locations: 

Manhattan: New York Skyports Seaplane Base - East 23rd St. & FDR Drive (2430 FDR Drive)
Google Maps:  https://goo.gl/maps/kNXni2JAbk82

Boston Harbor:  Fan Pier Marina, 1 Marina Park Drive, Boston
Google Maps: https://goo.gl/maps/RdJZe6vMfp8Jou1UA

Bridgeport Airport: 325 Main Street, Stratford, CT
Google Maps: https://goo.gl/maps/4mhNJBGZQbjLscsF7

East Hampton: East Hampton Airport @ 173 Daniels Hole Road  Wainscott, NY
Google Maps: https://goo.gl/maps/JcTH2Kbd4oD6fmrM6

Montauk Airport
Google Maps: https://goo.gl/maps/uSMv16L2jcMioiTKA

Shelter Island: We land off of Sunset Beach approx
Google Maps: https://goo.gl/maps/HAnzUBvymZq2DZ9x9

Special Shelter Island Instructions: 

* Flights to/from Shelter Island include a boat transfer from the beach (Sunset Beach) to the seaplane. Special instruction will be emailed to you before your flight. Uber is available from the beachfront. Please be aware that you may need to remove shoes and get your feet wet while entering/exiting the boat launch out to the seaplane. 

Please provide us with your dog’s weight and mobility status, so we can do the best we can to accommodate your animal.  In a fully booked flight, your pet’s weight will count towards your baggage allotment.  There is a maximum of 1 dog per flight.

We do not have a standard frequent flier program, however we do offer discounted commuter books and expanded flight options for frequent travelers. For more information, please contact info@flytailwind.com

We provide a variety of complimentary snacks and beverages (alcoholic and non-alcoholic) for your enjoyment in our lounges in Boston and Manhattan, as well as more limited choices while on board. If you have an allergy, please let us know beforehand.

No.  All children, including those under 2, must have their own ticket and be seated in a DOT-approved car seat.  If you will be traveling with your family, please book a seat for each passenger traveling, regardless of age. Please reference: https://www.faa.gov/passengers/fly_children/

Boston Harbor: there are several paid parking facilities available near the Fan Pier Marina 

Manhattan: There is paid parking directly above the East 23rd St. Skyport (NYS)

For both Boston Harbor and Manhattan, your most convenient option may be to take taxi, bus, or car service drop you off.  Even walking to your airplanes makes sense for some of our passengers!  

Low price or complimentary parking is also available at the Bridgeport, Easthampton, and Montauk Airports.

All Tailwind flights depart from private facilities and are thus not subject to standard commercial airport style security - no invasive TSA agents, lines, and you can keep your shoes on. All passengers are screened in advance against a national database, and may be denied boarding at crew or company discretion.

We suggest arriving 20 minutes before your departure time.  Anyone not present at least 10 minutes prior to departure may be denied boarding.

We are legally required to monitor the total weight of the aircraft and by providing your weight in advance, it helps us to plan efficiently and avoid delays. We use your weight information for flight planning purposes only.

For Scheduled Flights: 

Within 24 hours of a ticket purchase, passengers may cancel their reservation for a full refund. After that, only refundable tickets are eligible. 

Tailwind does not charge change fees. Reservations may be changed, subject to availability and any increase in fare up 90 minutes before departure. Reservations can also be cancelled and held as a future flight credit valid up to 1 year from the date of purchase.

Our new build Cessna Caravan Amphibians are fast, direct, and save you a lot of time. It is important to note that they also have weather and daylight limitations when landing on water (our crews and aircraft are capable and certified to take off and land at land airports like any other modern aircraft). Safety and transparency are key values for our company. In the event a flight appears unable to operate for any reason, we aim to communicate that to passengers as far in advance as practical, keeping in mind there are good (but slower) train, car, and airline alternatives between our destinations. All reservations for any impacted flight will be fully refundable.

For flights with departures before 11am, we will notify passengers by 7pm the day before the flight if the flight will not operate.

For flights between 11-3pm, we will notify passengers before 8am if a flight will not operate.

For flights after 3pm, we will notify passengers by 11am if a flight will not operate.

We are happy to assist with alternative arrangements.

On rare occasions governed by safety considerations, we may elect to land at a nearby land airport instead of the water on our Manhattan and Boston flights. This could be caused by unexpected weather, ATC, or other reasons and will be communicated as soon as possible to any affected passenger. In almost all cases, the diversion airports will be the Boston Logan private aviation terminal (BOS) or Teterboro (TEB) airports. Should such a diversion occur, passengers will be provided a $40 (Boston) or $80 (Manhattan) Visa/Amex gift card so that they can pay for alternative ground transport to their final destination.  

In the event Tailwind cancels or delays a flight for any reason, Tailwind will attempt to notify passengers in advance via the contact information submitted at the time of purchase. In the event of a flight cancellation, customers may choose between a refund or a credit good towards a future flight. We will assist with alternative arrangements to the extent possible. 

Please bring a valid ID.

We operate a fleet of late model, dependable and safe amphibious Cessna Caravans.  Easily recognizable with its wingspan of 52’, the versatile Caravan is known for its ability to get you where you really want to go- by land or by sea. See more here: https://www.flytailwind.com/fleet/

Tailwind Air is taking active steps in light of the COVID 19 virus to ensure that our operations remain safe, reliable, and clean.  We follow the guidance of the CDC and FAA and have active steps in place to reduce the risk of the virus. These include but are not limited to:

  • Enhanced cleaning, pre and post flight checks, and other precautions along with a detailed checklist that is completed before and after each flight. 
  • Only single use soft goods (sodas, cups, etc) will be used until further notice.
  • We strongly encourage passengers to bring their own masks and gloves.
  • Flight crews and staff will wear masks and gloves to the extent they do not interfere with flight safety, including during all loading, unloading, and check-in activity.
  • Crews are equipped with thermal temperature scanners and will deny boarding to anyone presenting an elevated body temperature.

through our partner iflysouthern.com