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

Where do you fly to?

From Manhattan or any body of water in the Northeast, you can charter our seaplane. Our seaplane has wheels and frequently flies from water to land and vice versa. Email info@flytailwind.com for a quote request.

Our land planes are based in White Plains (HPN) and Bedford (BED) but are able to pickup and drop you off anywhere in North America.

We also operate flights to/from the Hampton area in Long Island for our partner BlackBird.  Individual seats and season plans can be booked via the BlackBird app

On-demand charter is available to the Hamptons, Montauk, Martha’s Vineyard, Albany, Toronto, Washington, Baltimore, Chesapeake Bay, LBI, Bar Harbor, Lake George, you name it! For more see http://flytailwind.com/charter-services/

How much are tickets?

For individual seats, contact our partner BlackBird. Seaplane charters range from $3000-$8,000 for up to 8 people depending on a number of factors including distance, passenger total, landing fees, etc.

Can I bring luggage?

Yes.  A standard sized airline carry-on of 25 lbs. per person is included.  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 Skyport – 23rd & FDR Drive

Google Maps:  https://goo.gl/maps/kNXni2JAbk82

Boston: Signature Flight Support – Boston Logan

Google Maps: https://goo.gl/maps/vpNHvtCyyhq

Nantucket: Nantucket Memorial Airport

Google Maps: https://goo.gl/maps/jYriWrpK2KA2

Can I bring my pet with me?

Please provide us with your pet’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.  

Do you have a frequent flier program?

We do not have a standard frequent flier program, however we do offer discounted commuter tickets for frequent travelers as well as a friends and family referral program which can earn you major credit fast!

More information can be found here:


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.  Please reference: https://www.faa.gov/passengers/fly_children/

Where can I park my car?

There is third-party paid parking available near the 23rd St. Skyport (NYS), but your most convenient option is to have a taxi 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 your shoes on.

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, help us to plan efficiently and avoid delays. We only use your weight for planning purposes and will never disclose it publicly.  

What is the cancellation policy?

For Private Charter- Domestic

Unless otherwise noted on the trip itinerary, confirmed travel may be cancelled up to 24 hours prior to departure with no charge. After that time, a 100% cancellation fee will be incurred. If an aircraft has been relocated for the purposes of your flight, you will be charged for the cost of that relocation or 20% of the total cost – whichever is greater.

For Private Charter- International

Cancellation more than 10 days prior to the flight will result in a 25% charge of the total price. Cancellation within 10 days of the flight will result in a 50% charge of the total price. Cancellation within 24 hours of the flight will result in a 100% charge. A change fee of $100 may be charged for any changes made within 10 days of your charter.

What do I need to bring?

Please bring a valid ID.

What type of airplanes do you fly?  

We operate the dependable and safe amphibious Cessna Caravan.  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: http://flytailwind.com/fly-with-us/

We also operate several late model Socata TBM Turboprops, as well as multiple light and mid size jets.