NY • BOSTON • HAMPTONS • BRIDGEPORT

Buy a Shuttle Ticket

Manhattan, Boston, Hamptons, Provincetown and more

Book Ahead!

Flights to Boston Harbor, Manhattan, Plymouth & Nantucket will resume April 14th.

*Some restrictions apply.
See below for more details.
Now offering Sight-Seeing Charter Tours of Boston, Manhattan, and the Cape!
Now offering Sight-Seeing Charter Tours of Boston, Manhattan, and the Cape!

Fly with Tailwind Air - Boston Harbor to Manhattan

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Convenience in the Palm of Your Hand

Introducing the Tailwind Air App

Or look for the Tailwind Air Icon in the App Store

Tailwind’s seaplanes are the fastest
way in and out of Manhattan

Now offering our shuttle service from Manhattan to Boston!

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.

Weekend Getaway

Specials to Boston and New York from
$595 roundtrip.

Tailwind Coverage Highlights

Fly with Tailwind Air - Boston Harbor to Manhattan

The Latest From Social Media

Entering the weekend like a fleet of seaplanes: ma Entering the weekend like a fleet of seaplanes: making a splash at the Boston Marathon! 🌊✈️ Tailwind Air Fastest way between NY and BOS, without needing to SOAR! 🏁🏃‍♂️ 

#BostonMarathon #SeaplaneSquad #WeekendVibes
#patriotsday #nyc #boaton #flythefastlane

Entering the weekend like a fleet of seaplanes: making a splash at the Boston Marathon! 🌊✈️ Tailwind Air Fastest way between NY and BOS, without needing to SOAR! 🏁🏃‍♂️

#BostonMarathon #SeaplaneSquad #WeekendVibes
#patriotsday #nyc #boaton #flythefastlane
...

𝐃𝐨 𝐲𝐨𝐮 𝐤𝐧𝐨𝐰 𝐰𝐡𝐚𝐭 𝐭𝐢𝐦𝐞 𝐢𝐭 𝐢𝐬? 
💙✈️ Yes!! It's #SeaplaneSeason ✈️💙
#flythefastlane with @tailwindair 

#manhattan #nyc #nytraffic #nytrip #boston #bostontonyc #roadtrip #seaplane #DiscoverNewPlaces #disruptingregionalmobility #urbanmobility #smarttravel #acelaexpress #train

𝐃𝐨 𝐲𝐨𝐮 𝐤𝐧𝐨𝐰 𝐰𝐡𝐚𝐭 𝐭𝐢𝐦𝐞 𝐢𝐭 𝐢𝐬?
💙✈️ Yes!! It's #SeaplaneSeason ✈️💙
#flythefastlane with @tailwindair

#manhattan #nyc #nytraffic #nytrip #boston #bostontonyc #roadtrip #seaplane #DiscoverNewPlaces #disruptingregionalmobility #urbanmobility #smarttravel #acelaexpress #train
...

Meet Olivia 🎹🐕🛬! A British citizen with a Meet Olivia 🎹🐕🛬! A British citizen with a minor in Spanish, a talented pianist, and a dog-lover!

Joining the sales team to take Tailwind Air  shuttle service to new heights! 

Get ready to fly in style and experience the fastest way in and out of Boston and Manhattan 🛫🗽💨✨ 

Welcome @oleach9 to the #dreamteam

#AviationEnthusiast #SalesForce #BostonToManhattan #PianoAndPuppies 🎶🐾 #regionalmobility #businesstrip #womeninaviation #business #sustainability #airliner #urbanmobility #seaplane #fly #travel #innovation #BreakingBarriers #privateflying #flythefastlane

Meet Olivia 🎹🐕🛬! A British citizen with a minor in Spanish, a talented pianist, and a dog-lover!

Joining the sales team to take Tailwind Air shuttle service to new heights!

Get ready to fly in style and experience the fastest way in and out of Boston and Manhattan 🛫🗽💨✨

Welcome @oleach9 to the #dreamteam

#AviationEnthusiast #SalesForce #BostonToManhattan #PianoAndPuppies 🎶🐾 #regionalmobility #businesstrip #womeninaviation #business #sustainability #airliner #urbanmobility #seaplane #fly #travel #innovation #BreakingBarriers #privateflying #flythefastlane
...

Ready, set, RUN to the finish line with Tailwind A Ready, set, RUN to the finish line with Tailwind Air! 🏃‍♂️💨 Fly faster than the competition and arrive in style for the Boston Marathon 🏆

#BostonMarathon2023 #TailwindAirTakeoff 🛬🌃
#runthefastlane #flythefastlane

Ready, set, RUN to the finish line with Tailwind Air! 🏃‍♂️💨 Fly faster than the competition and arrive in style for the Boston Marathon 🏆

#BostonMarathon2023 #TailwindAirTakeoff 🛬🌃
#runthefastlane #flythefastlane
...

🐾 ℙ𝕒𝕨𝕤-𝕚𝕥𝕚𝕧𝕖𝕝𝕪 🐾 ℙ𝕒𝕨𝕤-𝕚𝕥𝕚𝕧𝕖𝕝𝕪 thrilled to welcome our furry friends on board at Tailwind Air! ✈️ Creating unforgettable family memories, one 𝕨𝕒𝕘 at a time 🐕💕

#FlyWithFido #PetFriendlyTravel #TailwindAir #flythefastlane 🌎🐾

🐾 ℙ𝕒𝕨𝕤-𝕚𝕥𝕚𝕧𝕖𝕝𝕪 thrilled to welcome our furry friends on board at Tailwind Air! ✈️ Creating unforgettable family memories, one 𝕨𝕒𝕘 at a time 🐕💕

#FlyWithFido #PetFriendlyTravel #TailwindAir #flythefastlane 🌎🐾
...

✈️🌞 Elevate your summer with Tailwind's exc ✈️🌞 Elevate your summer with Tailwind's exclusive charter packs! 🛩️ Enjoy flexibility, luxury, and savings on private flights within 150 miles of NYC. 🌆 Buy 6 or 10 pack & get 10% off scheduled flights too! 🤑 Hurry, don't miss out! 📧

Email for details reservations@flytailwind.com 
#FlyTailwind #flythefastlane #LuxuryTravel #PrivateCharter #SummerGetaway #NYCDeals 🏖️😎

✈️🌞 Elevate your summer with Tailwind's exclusive charter packs! 🛩️ Enjoy flexibility, luxury, and savings on private flights within 150 miles of NYC. 🌆 Buy 6 or 10 pack & get 10% off scheduled flights too! 🤑 Hurry, don't miss out! 📧

Email for details reservations@flytailwind.com
#FlyTailwind #flythefastlane #LuxuryTravel #PrivateCharter #SummerGetaway #NYCDeals 🏖️😎
...

@pmckeats COO at @drinkcirkul shares his experienc @pmckeats COO at @drinkcirkul shares his experience flying Tailwind Air.

Boston to Manhattan in just 1hr!🚀 Tailwind made my trip hassle-free & gateless! 🤩 Goodbye crowds, hello adventure! 🗽

#TailwindTrippin #NoGatesNoProblem #FlyAndSmile 😎✈️🌟
#flythefastlane #tailwindair #drinkcirkul

@pmckeats COO at @drinkcirkul shares his experience flying Tailwind Air.

Boston to Manhattan in just 1hr!🚀 Tailwind made my trip hassle-free & gateless! 🤩 Goodbye crowds, hello adventure! 🗽

#TailwindTrippin #NoGatesNoProblem #FlyAndSmile 😎✈️🌟
#flythefastlane #tailwindair #drinkcirkul
...

✨💎 Introducing a match made in luxury heaven! ✨💎 Introducing a match made in luxury heaven! We're thrilled to announce the exclusive partnership between Tailwind Air and St. Regis Residences Boston. 🌟🌃

🌊 As an expert home buyer, we can assure you that St. Regis Residences Boston takes extraordinary living to new heights! 🏙️🥂 Discover the epitome of elegance and sophistication with unparalleled amenities, services, and breathtaking views of the city skyline. ✨🌉

🛩️✈️ Tailwind Air is excited to elevate your St. Regis experience with exclusive private fares on our state-of-the-art seaplanes. 🌊✨ Enjoy seamless concierge booking access and indulge in the ultimate convenience with pick-up and drop-off services right at your back door. 🚪💼

💼🌟 Live life in the fast lane and let us whisk you away to your favorite destinations! 🏖️🌆

#TailwindAirXStRegisBoston #ExtraordinaryLiving #LuxuryTravel #SeaplaneExperience #StRegisResidences #BostonLuxury #CitySkyline #PrivateFares #ConciergeAccess #TailwindAir #StRegisBoston 🌟🌊🏙️✈️🌃💎✨

✨💎 Introducing a match made in luxury heaven! We're thrilled to announce the exclusive partnership between Tailwind Air and St. Regis Residences Boston. 🌟🌃

🌊 As an expert home buyer, we can assure you that St. Regis Residences Boston takes extraordinary living to new heights! 🏙️🥂 Discover the epitome of elegance and sophistication with unparalleled amenities, services, and breathtaking views of the city skyline. ✨🌉

🛩️✈️ Tailwind Air is excited to elevate your St. Regis experience with exclusive private fares on our state-of-the-art seaplanes. 🌊✨ Enjoy seamless concierge booking access and indulge in the ultimate convenience with pick-up and drop-off services right at your back door. 🚪💼

💼🌟 Live life in the fast lane and let us whisk you away to your favorite destinations! 🏖️🌆

#TailwindAirXStRegisBoston #ExtraordinaryLiving #LuxuryTravel #SeaplaneExperience #StRegisResidences #BostonLuxury #CitySkyline #PrivateFares #ConciergeAccess #TailwindAir #StRegisBoston 🌟🌊🏙️✈️🌃💎✨
...

Get ready to fly to new heights with Tailwind's ne Get ready to fly to new heights with Tailwind's new season starting this Friday, April 14th! 

Our team has been working tirelessly to bring you the most exciting and exhilarating adventure yet, filled with twists, turns, and breathtaking views. 

Whether you're a seasoned veteran or a first-time flyer, we guarantee you won't want to miss this. So fasten your seatbelts and get ready for the ride of a lifetime with Tailwind!
 
#TailwindTakeoff #NewSeasonNewAdventures #BuckleUpAndFlyHigh #flythefastlane #April14 #NewSeasonNewAdventures #newseason #seaplane #2023 #sprinhassprung

Get ready to fly to new heights with Tailwind's new season starting this Friday, April 14th!

Our team has been working tirelessly to bring you the most exciting and exhilarating adventure yet, filled with twists, turns, and breathtaking views.

Whether you're a seasoned veteran or a first-time flyer, we guarantee you won't want to miss this. So fasten your seatbelts and get ready for the ride of a lifetime with Tailwind!

#TailwindTakeoff #NewSeasonNewAdventures #BuckleUpAndFlyHigh #flythefastlane #April14 #NewSeasonNewAdventures #newseason #seaplane #2023 #sprinhassprung
...

"It is a bird's imagination, not its wings, that d "It is a bird's imagination, not its wings, that determines how high it can fly"

#mondaymotivation #flythefastlane #FlyHigh #fearless #limitless #DreamBig #seizetheday #seizethemoment #tailwindair #inspiration #disruptingregionalmobility #dream

"It is a bird's imagination, not its wings, that determines how high it can fly"

#mondaymotivation #flythefastlane #FlyHigh #fearless #limitless #DreamBig #seizetheday #seizethemoment #tailwindair #inspiration #disruptingregionalmobility #dream
...

🎵 Start spreading the news, Tailwind is startin 🎵 Start spreading the news, Tailwind is starting the new seaplane season on April 14th!

We hope you are as excited as @thekalenallen is when singing Frank Sinatra's  classic "New York, New York" while flying over the Big Apple.

#FlyingHigh #TailwingAdventures #NewYorkNewYork #flythefastlane #kallenallen #ellendegeneresshow #manhattan #sinatra #NewYorkNewYork #disruptingregionalmobility #CityThatNeverSleeps

@ellendegeneres @enews @entertainmenttonight

🎵 Start spreading the news, Tailwind is starting the new seaplane season on April 14th!

We hope you are as excited as @thekalenallen is when singing Frank Sinatra's classic "New York, New York" while flying over the Big Apple.

#FlyingHigh #TailwingAdventures #NewYorkNewYork #flythefastlane #kallenallen #ellendegeneresshow #manhattan #sinatra #NewYorkNewYork #disruptingregionalmobility #CityThatNeverSleeps

@ellendegeneres @enews @entertainmenttonight
...

Entering the weekend like a Hall of Famer - soarin Entering the weekend like a Hall of Famer - soaring high in a seaplane, leaving all your worries behind! ✈️🙌⚾️ 

#WeekendVibes #PedroMartinez #SeaplaneGoals
#tailwindair #flythefastlane #goals #hof2022 #baseball #cooperstown #likeaboss #revolutionizingregionalmobility #disrupt #seaplane

Entering the weekend like a Hall of Famer - soaring high in a seaplane, leaving all your worries behind! ✈️🙌⚾️

#WeekendVibes #PedroMartinez #SeaplaneGoals
#tailwindair #flythefastlane #goals #hof2022 #baseball #cooperstown #likeaboss #revolutionizingregionalmobility #disrupt #seaplane
...

Luck o' the seaplane to all our Tailwind friends t Luck o' the seaplane to all our Tailwind friends this St. Patrick's Day! 

May the luck of the Irish fly with you on this day of green shenanigans and high-flying fun.

Wishing your day is as smooth as the Irish sea, and your adventures take you to new heights 🍀✈️🌊 

#tailwind #stpatricksday #flythefastlane  #luckoftheirish #seaplaneadventures #flightgoals #adventureawaits ✈️🍀 #TailwindLuck #FlyingGreen #irish #travel #dublin #celebrate #ireland #boston #manhattan  #SeaplaneShenanigans 🌊🛩️🌈

Luck o' the seaplane to all our Tailwind friends this St. Patrick's Day!

May the luck of the Irish fly with you on this day of green shenanigans and high-flying fun.

Wishing your day is as smooth as the Irish sea, and your adventures take you to new heights 🍀✈️🌊

#tailwind #stpatricksday #flythefastlane #luckoftheirish #seaplaneadventures #flightgoals #adventureawaits ✈️🍀 #TailwindLuck #FlyingGreen #irish #travel #dublin #celebrate #ireland #boston #manhattan #SeaplaneShenanigans 🌊🛩️🌈
...

🎉👏 Let's all give a big shoutout to Emily Cr 🎉👏 Let's all give a big shoutout to Emily Crofutt, Tailwind's licensed FAA airframe and powerplant mechanic! 🛩️🔧 

Emily has been an invaluable member of our team, ensuring that our aircraft are always safe and in top working condition. 

Her dedication, skill, and attention to detail are second to none! 🙌 

#Tailwind #AirplaneMechanic #FAA #LicensedMechanic #Aviation #SafetyFirst 🛫✈️🛬

🎉👏 Let's all give a big shoutout to Emily Crofutt, Tailwind's licensed FAA airframe and powerplant mechanic! 🛩️🔧

Emily has been an invaluable member of our team, ensuring that our aircraft are always safe and in top working condition.

Her dedication, skill, and attention to detail are second to none! 🙌

#Tailwind #AirplaneMechanic #FAA #LicensedMechanic #Aviation #SafetyFirst 🛫✈️🛬
...

Hey everyone! 🤗 We want to make sure you stay i Hey everyone! 🤗 We want to make sure you stay in the know about the latest news, events and offers.

 📰 Follow us on all social media accounts to get the scoop and never miss a beat! 🎉 

We are always offering something new and exciting, so don't miss out - follow us on IG, FB, TW, TIKTOK,Hey everyone! 🤗 We want to make sure you stay in the know about the latest news, events and offers. 📰 Follow us on our social media accounts to get the scoop and never miss a beat! 🎉 We are always offering something new and exciting, so don't miss out - follow us now! 🙌 #FollowUs #StayInTheKnow #ExcitingUpdates 🤩 Tailwind Air  @ TailwindAir

🙌 #FollowUs #StayInTheKnow #ExcitingUpdates 🤩

Hey everyone! 🤗 We want to make sure you stay in the know about the latest news, events and offers.

📰 Follow us on all social media accounts to get the scoop and never miss a beat! 🎉

We are always offering something new and exciting, so don't miss out - follow us on IG, FB, TW, TIKTOK,Hey everyone! 🤗 We want to make sure you stay in the know about the latest news, events and offers. 📰 Follow us on our social media accounts to get the scoop and never miss a beat! 🎉 We are always offering something new and exciting, so don't miss out - follow us now! 🙌 #FollowUs #StayInTheKnow #ExcitingUpdates 🤩 Tailwind Air @ TailwindAir

🙌 #FollowUs #StayInTheKnow #ExcitingUpdates 🤩
...

Attention all experienced sales professionals! Tai Attention all experienced sales professionals! Tailwind Air, the leading seaplane schedule services and charter airline in the North East, is seeking a Director of Sales to help develop the Boston, NY, and DC markets. This is an exciting opportunity to join a growing company and make a real impact in the aviation industry.

To be successful in this role, candidates must have significant corporate airline experience and a proven track record of building and managing successful sales teams. As Director of Sales, you will be responsible for driving revenue growth and expanding Tailwind Air's customer base in key markets. You will work closely with other departments to develop sales strategies, manage sales operations, and ensure a high level of customer satisfaction.

At Tailwind Air, we are committed to providing safe, reliable, and comfortable air travel to our customers. As Director of Sales, you will play a key role in achieving this mission and helping us continue to grow and succeed. Don't miss out on this exciting opportunity - apply now and take your career to new heights with Tailwind Air!

Attention all experienced sales professionals! Tailwind Air, the leading seaplane schedule services and charter airline in the North East, is seeking a Director of Sales to help develop the Boston, NY, and DC markets. This is an exciting opportunity to join a growing company and make a real impact in the aviation industry.

To be successful in this role, candidates must have significant corporate airline experience and a proven track record of building and managing successful sales teams. As Director of Sales, you will be responsible for driving revenue growth and expanding Tailwind Air's customer base in key markets. You will work closely with other departments to develop sales strategies, manage sales operations, and ensure a high level of customer satisfaction.

At Tailwind Air, we are committed to providing safe, reliable, and comfortable air travel to our customers. As Director of Sales, you will play a key role in achieving this mission and helping us continue to grow and succeed. Don't miss out on this exciting opportunity - apply now and take your career to new heights with Tailwind Air!
...

As the sun rises, the seaplane season is fast appr As the sun rises, the seaplane season is fast approaching. 

Get ready to explore the world from a new perspective and purchase your commuter book or tickets now for an unforgettable experience! 

Enjoy the beauty of flight with the freedom of the open sky and make memories to last a lifetime.

 #regionalmobility #businesstrip #womeninaviation #business #sustainability #airliner #urbanmobility #seaplane #fly #travel #innovation #BreakingBarriers #privateflying #flythefastlane

As the sun rises, the seaplane season is fast approaching.

Get ready to explore the world from a new perspective and purchase your commuter book or tickets now for an unforgettable experience!

Enjoy the beauty of flight with the freedom of the open sky and make memories to last a lifetime.

#regionalmobility #businesstrip #womeninaviation #business #sustainability #airliner #urbanmobility #seaplane #fly #travel #innovation #BreakingBarriers #privateflying #flythefastlane
...

"Discover Tailwind's Exciting New Headquarters - O "Discover Tailwind's Exciting New Headquarters - Open Now!"

Tailwind Air is thrilled to announce the opening of its new headquarters in Port Chester, NY. Here, more than 50 Tailwind Air employees are working hard to manage the business operations, leveraging their expertise and enthusiasm to create something truly remarkable. We invite you to join us in celebrating this momentous occasion and get a glimpse of the future of Tailwind Air!

 #WomenInAviation #inspiration #flythefastlane #respect #privateflying #DiversityMatters #InclusionWorks #TailwindAir #ExperiencedPilot #PilotLife #TailwindAirlines #ExecutiveTravel #TailwingAirProud #love

"Discover Tailwind's Exciting New Headquarters - Open Now!"

Tailwind Air is thrilled to announce the opening of its new headquarters in Port Chester, NY. Here, more than 50 Tailwind Air employees are working hard to manage the business operations, leveraging their expertise and enthusiasm to create something truly remarkable. We invite you to join us in celebrating this momentous occasion and get a glimpse of the future of Tailwind Air!

#WomenInAviation #inspiration #flythefastlane #respect #privateflying #DiversityMatters #InclusionWorks #TailwindAir #ExperiencedPilot #PilotLife #TailwindAirlines #ExecutiveTravel #TailwingAirProud #love
...

The stars are aligning for the 𝕋𝕙𝕖 𝕆𝕤𝕔𝕒𝕣 winners! 🤩 We here at Tailwind Air are sending you a huge congratulations for reaching new heights. 

Keep up the great work and continue soaring higher and higher! 🛩️ 

#TailwindAir #OSCARS #reachforthestars #everythingeverywhereallatonce  #𝕗𝕝𝕪𝕥𝕙𝕖𝕗𝕒𝕒𝕤𝕥𝕝𝕒𝕟𝕖 #newhights #regionalmobility #businesstrip #womeninaviation #business #sustainability #airliner #urbanmobility #seaplane #fly #travel #innovation #BreakingBarriers #privateflying #flythefastlane

The stars are aligning for the 𝕋𝕙𝕖 𝕆𝕤𝕔𝕒𝕣 winners! 🤩 We here at Tailwind Air are sending you a huge congratulations for reaching new heights.

Keep up the great work and continue soaring higher and higher! 🛩️

#TailwindAir #OSCARS #reachforthestars #everythingeverywhereallatonce #𝕗𝕝𝕪𝕥𝕙𝕖𝕗𝕒𝕒𝕤𝕥𝕝𝕒𝕟𝕖 #newhights #regionalmobility #businesstrip #womeninaviation #business #sustainability #airliner #urbanmobility #seaplane #fly #travel #innovation #BreakingBarriers #privateflying #flythefastlane
...

A note about East Hampton Airport service:

As many are aware, East Hampton is in the process of converting to a private, town controlled airport. Tailwind Air will continue to offer service to the airport while complying with new constraints imposed on operators to the airport. The new town imposed frequency limitations, large fee increases, and restrictive curfews at the airport have driven up operating costs substantially versus prior years.  In addition to offering service to East Hampton, Tailwind will also offer service to nearby Sag Harbor as well as Shelter Island and Montauk. Tickets and commuter books purchased for East Hampton Airport will be honored on all flights to the Hamptons, including Sag Harbor.  Tickets and commuter books purchased for Sag Harbor or Shelter cannot be used for East Hampton Airport unless a $200 per ticket surcharge is charged separately. On occasion, our aircraft to East Hampton Airport may divert to alternate landing areas in order to comply with the new airport restrictions.

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