Tailwind FAQs


We hope this FAQ will help answer your questions about Tailwind Air – or drop us a line at info@flytailwind.com

Where do you fly to?
From Manhattan, we have scheduled service to East Hampton, Shelter Island, and Montauk.  For details visit: https://www.flytailwind.com/hamptons-beaches/

On-demand 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/

How can I book a flight?
For our scheduled flights, you can book a flight via our website or through our codeshare 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 is at 212-328-9145. We offer discounted books of 10 and 20 tickets and extra perks for those who travel frequently. Charter inquiries should be directed to charter@flytailwind.com

My ticket says Southern Airways on it, what gives?
Southern Airways is a codeshare 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!

How much are tickets?
Ticket prices vary, but begin at $695 one way for our Long Island destinations. We also have occasional $99 fares for certain off peak flights.  Further discounts are available through multi-ticket commuter packs as well as round trip fares. For commuter books, please contact amcdonald@flytailwind.com. To book online, go to http://flytailwind.com

Can I bring luggage?
Yes.  A standard sized airline carry-on of 20 lbs. is included with your fare on Tailwind Scheduled service.  For larger 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.

Where does my flight leave/arrive from?

Terminal Locations:

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

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

* 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.

Can I bring my dog with me?
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.

Do you have a frequent flier program?
We do not have a standard frequent flier program, however we do offer discounted commuter books and expanded flight option for frequent travellers. For more information on commuter books, contact amcdonald@flytailwind.com

Is there meal service on board?
We provide a variety of complimentary snacks and beverages (alcoholic and non-alcoholic) for your enjoyment.  If you have an allergy, please let us know beforehand.

Can my child sit on my lap?
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/

Where can I park my car?
There is third-party paid parking available near the East 23rd St. Skyport (NYS), but your most convenient option is to have a taxi, bus, or car service drop you off.  Parking is complimentary at most airports we fly to.

Should I allow time to pass through security?  Will I be patted down?
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 you shoes on. All passengers are screened in advance against a national database, and may be denied boarding at the crew’s or company’s discretion.

How early do I need to arrive?
Please arrive 20 minutes before your departure time.

Why does Tailwind need to know my weight?
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 only use your weight for important flight planning purposes.

What is the cancellation policy?
For Scheduled Flights: 

Within 24 hours of a ticket purchase, passengers may cancel their reservation for a full refund.

Up to 48 hours prior to departure time, passengers may change flights for a $75 change fee plus any increase in fare. Alternatively, reservations cancelled during this period will be allowed to apply the price of the purchased ticket to future travel on Tailwind for up to one (1) year after the purchase date.

Cancellations and missed flights within 48 hours will result in the loss of fare.

In the event Tailwind cancels or severely 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.

For Private Charter- Domestic and International

  • Any cancellation within 48 hours of scheduled departure for domestic Charter Trips or within 72 hours of scheduled departure for international Charter Trips will result in a cancellation fee of 100% of the fees indicated on the Quote.
  • Any cancellations more than 48 hours prior to scheduled departure for domestic Charter Trips or more than 72 hours prior to scheduled departure for international Charter Trips, will result in cancellation fees (not to exceed the cost of the canceled trip) equal to the (i) any costs incurred by Tailwind and the air carrier in preparation for the cancelled trip, including positioning/repositioning an aircraft and flight crew in preparation for the cancelled trip, or (ii) charges equivalent to one hour of flight time in turbo props, or two hours of flight time in jet aircraft, whichever is greater.
  • Except as described in this section, Client will not be charged other cancellation fees for flights cancelled more than 48 hours prior to scheduled departure for domestic Charter Trips, or more than 72 hours prior to scheduled departure for international Charter Trips, except in the following circumstances: (i) when an advance deposit is required for a firm reservation, some or all of the deposit may be payable as a cancellation fee, or (ii) when Tailwind has, at or prior to the time the Client makes a firm reservation, notified Client that there will be a cancellation fee, (iii) if Tailwind incurs any costs in preparation for the cancelled trip, including positioning/repositioning an aircraft and flight crew in preparation for the cancelled trip.
  • All round trip bookings are 100% refundable within 24 hours of booking if they are outside of the 48 hour domestic and 72 hour international windows described in this section.
  • Amounts payable under this section are not to be deemed as penalties, but rather shall be paid to Tailwind for Tailwind’s actual expense and damage caused by cancellation.

What do I need to bring?
Please bring a valid ID.

What type of airplanes do you fly?
We operate a fleet of 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/

What steps are you taking to minimize Covid-19?
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