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, we have scheduled service to Boston and Nantucket.  For details visit: http://flytailwind.com/schedules-fares/

We also operate scheduled flights to East Hampton which can be booked via www.flyblade.com

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?

Ticket prices vary, but begin around $500 one way. Discounts are available through multi-ticket commuter packs as well as round trip fares. For the latest see: http://flytailwind.com/schedules-fares/

Can I bring luggage?

Yes.  A standard sized airline carry-on of 25 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 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 for frequent travellers 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.  If you will be traveling with your family, please call a Tailwind representative as we offer discounted fares for children. 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 Scheduled Flights:

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

Up to 72 hours prior to departure time, passengers may change flights without penalty (although must pay any increase in fare). Alternately, 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.

Reservations cancelled within 72 hours will incur a 50% rebooking fee based on the original price of the ticket. All tickets are non-refundable.

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 chose 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

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 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: http://flytailwind.com/fly-with-us/