We have scheduled service to Manhattan, Boston Harbor, Nantucket, Plymouth, Bridgeport, East Hampton, Shelter Island, and Provincetown, MA. Washington, DC scheduled service will resume in Fall 2023. For details, see our schedule.

On-demand seaplane charter is available to the Washington, DC, TheHamptons, Martha’s Vineyard, Nantucket, Albany, Toronto, Washington, Baltimore, Chesapeake Bay, LBI, Bar Harbor, upper Vermont and New Hampshire, Lake George, you name it!

Tailwind Air also directly operates a complete range of charter aircraft from intercontinental jets to fast 5 passenger regional turboprops. For more information, visit our charters page.

For our daily scheduled flights, you can book a flight via our website or through our code-share partner Southern Airways . 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 chartersales@flytailwind.com

For a more detailed guide to help take you through our online booking process, see our step-by-step walkthroughs for booking Fast Lane Memberships and Commuter Books.

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

Weight and balance are important elements of flying with Tailwind Air. Your ticket includes a normal sized carry-on/roll aboard up to 20lbs for scheduled service between Manhattan/Boston,  Manhattan/Provincetown, Manhattan/Newport, Manhattan/Plymouth, and Manhattan/Washington, DC.

Flights from Boston/Nantucket, Boston/Provincetown, Boston/Plymouth, Manhattan/Shelter Island and Manhattan/Bridgeport include a normal sized carry-on/roll aboard up to 25lbs.

Excess baggage beyond this limit will incur a $250 fee for each additional bag up to 50lbs. For safety considerations, we cannot guarantee any checked bag will be accepted onto the flight and we may have to ship via overnight freight company or a later flight. Please contact us well in advance if you will have excess baggage or arrange for alternative baggage shipping in advance.

No single bag may exceed 50lbs.

Passengers may purchase a seat (if available) at the prevailing rate, which allows an additional 125lbs of luggage.

Our passengers are able to receive a 15% discount with Luggage Free. Have your bag shipped directly to your destination by using the below link. Luggage Free is a full-service luggage shipping company. Luggage Free eliminates the hassle of traveling with your luggage by providing door-to-door service. Please visit Luggage Free's website  to arrange your luggage and receive the 15% discount.

Terminal Locations: 

Boston Harbor: ReelHouse Oyster Bar – Seaport
10 Waterside Avenue
Boston, MA, 02210

Manhattan: New York Skyports Seaplane Base — East 23rd St. & FDR Drive (2430 FDR Drive, New York, NY)
When you arrive, look for the seaplane base entrance and our signage to the left of the waterside parking garage as you face the East River. Please allow extra time due to ongoing roadwork near the FDR drive!

Nantucket: Nantucket Memorial Airport FBO — 14 Airport Rd, Nantucket, MA
Pilots will meet passengers in the waiting area of the private aviation lounge. The private aviation terminal is located to the right of the main terminal when facing the airport from the main entrance.

Plymouth Municipal Airport:
246 South Meadow Road
Plymouth, MA 02360

Shelter Island: *
We land off of Sunset Beach approx.

* Flights to/from Shelter Island include a boat transfer from the beach (Sunset Beach) to the seaplane. Special instructions 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.

Provincetown Municipal Airport:
176 Race Point Road
Provincetown, MA 02657

Newport State Airport:
211 Airport Access Rd
Middletown, RI 02842

Washington, DC - Dulles International Airport:
Jet Aviation FBO –  (private terminal)
23411 Autopilot Dr, Dulles, VA 20166

Bridgeport Sikorsky Memorial Airport:
325 Main Street
Stratford, CT 06615

We love animals, but only dogs can travel as pets onboard our flights. Please tell us in advance if you will be traveling with a dog.  There is a maximum of 1 dog per flight, or 2 dogs if from the same dog family.  Dogs weighing up 25 pounds can travel in an approved carrier at no additional cost. For dogs over 25 lbs, you will be asked to purchase an adjacent seat at the prevailing rate. Our customer support team will be happy to help you with this.

We do not have a traditional frequent flier program, however you can earn free flights quickly through our referral program, where you can offer friends a family a 10% discount on their first flight with us, and you can earn $75 credits valid as cash for all our scheduled and charter flights. Contact info@flytailwind.com to obtain your referral code. 

Purchase a Fast Lane Club membership and save up to 60% off regular full fare tickets. Enjoy unlimited access on flights between Manhattan, DC, Boston, Sag Harbor Bay, East Hampton, Montauk, and Shelter Island.

We also sell discounted commuter ticket books in packs of 10, 20 and 50 flight segments. These books importantly give you access to every seat in our plane. 

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 the FAA’s policies regarding this. 

Washington, DC — IAD: Free validated parking outside the Jet Aviation FBO (private terminal - Starting October 11th).

Boston Harbor: There is no set parking at ReelHouse. There is independent street/garage parking available. Prices will vary based on wherever you choose to park. 

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

Provincetown: Complimentary parking at the Provincetown Municipal Airport.

For both Boston Harbor and Manhattan, your most convenient option may be to take taxi, bus, or car service drop-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 Nantucket Municipal 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.

Any passenger that does not show up for a flight that they hold an active reservation for will forfeit the value paid for the flight and will not be eligible for a refund. This policy applies to all ticket forms, including refundable tickets, Fast Lane tickets, and Commuter Book tickets.

After a ticket is purchased, within 24 hours of purchase, passengers may cancel and refund their reservation with no penalty, provided the flights booked are more than 7 days away from departure. After this initial period of 24 hours post purchase, customers may change flights with no penalty or obtain a refund if the ticket is clearly listed as a refundable ticket. 

Non refundable or Fast Lane tickets canceled or changed 72-25 hours before departure time on Manhattan/Provincetown, Manhattan/Newport, Manhattan/Shelter are subject to a $150 change/cancel fee.

Non-refundable or Fast Lane reservations changed within 24 hours of the departure time will be subject to a $350 change fee  ($150 fee on Boston-Nantucket and Boston-Provincetown flights only) plus any difference in fare.

Non-refundable or Fast Lane reservations canceled within 24 hours of the departure time will have no future value.

Cancel/Change Rules for Commuter Book Reservations:
Commuter book tickets may be changed within 24 hours of departure, however a $350 fee will be assessed separately before the credit is refunded to your account. Any Commuter book tickets reservation canceled within 24 hours of departure will have no future value.

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. Non refundable reservations cancelled due to weather or other factor beyond our control, will not be eligible for a refund, but are eligible for future flight credit. 

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 some occasions governed by safety considerations, we may elect to land at a nearby land airport instead of the water on your flights.  Flights to/from Manhattan and the Hamptons area (Shelter, Sag Harbor, East Hampton) that cannot access Manhattan Skyport (NYS) will be canceled.  This will be communicated as soon as possible to any affected passenger before the flight, or on rare occasions in flight by a crew member. In almost all cases, the diversion airports will be the Norwood Airport (OWD) for Boston Harbor bound flights or Westchester County Airport (HPN) - Atlantic West FBO for Manhattan bound flights. Tailwind Air will book a rideshare vehicle for pax or provide a future flight credit to cover reasonable rideshare cost to/from your diversion airport. Rideshare credit does not apply to Nantucket-Boston Harbor flights.   

If we elect to use a diversion airport, unused non-refundable reservations will not be eligible for a refund, but are eligible for future flight credit.  In the event of a flight diversion that is not weather related or beyond our control, customers may choose between a refund or a credit towards a future flight. 

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. 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. 

Mask use is optional, unless required by any current FAA directive at the time of flight. We encourage mask use based on individual preferences.

If you feel unwell or have recently tested positive for the COVID-19 virus, you must call us in advance and we will rebook your flight or provide a credit towards a future flight. A refund is available for refundable tickets. Failure to notify us in advance will result in forfeiture of the fare paid. A positive test result from a laboratory may be required.