NY • BOSTON • HAMPTONS • BRIDGEPORT

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Manhattan, Boston, Hamptons, Provincetown, DC and more

Book Ahead!

Flights to Manhattan, Boston, and Washington DC will resume March 21st.

*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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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 both Boston and Washington, DC!

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

The Bahamas is an escape for everyone who loves to The Bahamas is an escape for everyone who loves to be in touch with the wonders of nature.🌴

The white sand and turquoise water from multiple islands are just the start of this incredible trip.

Book your flight and fall in love with this archipelago.

#tailwindair #flytailwind #flytailwindair #flythefastlane #archipelago #bahamas #beach #thecaribbean #sun #travelers #travel #shuttleservice #seaplanes #jets #charters

The Bahamas is an escape for everyone who loves to be in touch with the wonders of nature.🌴

The white sand and turquoise water from multiple islands are just the start of this incredible trip.

Book your flight and fall in love with this archipelago.

#tailwindair #flytailwind #flytailwindair #flythefastlane #archipelago #bahamas #beach #thecaribbean #sun #travelers #travel #shuttleservice #seaplanes #jets #charters
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@tailwindair is the next level to traveling and @k @tailwindair is the next level to traveling and @kimberly.pucci knows that!✨

Embrace the elevated experience to reach your favorite destinations by booking your flight.

#tailwindair #flytailwind #flytailwindair #travelers #travel #shuttleservice #seaplanes #jets #charters

@tailwindair is the next level to traveling and @kimberly.pucci knows that!✨

Embrace the elevated experience to reach your favorite destinations by booking your flight.

#tailwindair #flytailwind #flytailwindair #travelers #travel #shuttleservice #seaplanes #jets #charters
...

It's your time to win!🎉 From this January 30th It's your time to win!🎉

From this January 30th through February 15th, Tailwind Air and its partner, Kimberly Pucci, are teaming up to offer our customers a sensational prize: win a round trip to Manhattan or Boston during the 2023 season, plus a KP gorgeous purse!

Prize value:
KP weekender $2100
Tailwind flight $3100
Total: $5200

What do you have to do to participate?👇

1️⃣ Mention 3 friends.
2️⃣ Follow @kimberly.pucci and us.
3️⃣ Like this post.
4️⃣ Share in stories and tag us.

Make sure you follow all FOUR steps.

The winner will be announced on 02/17 at 4 PM via TW Instagram.🏆

Please note flights must be booked for march, 2023.
No purchase necessary to enter Sweepstake.
Terms and conditions apply.
The winner must be located in the US.⁠

It's simple, so participate and have a great year by flying the fast lane!

This promotion is in no way sponsored, administered, or associated with Instagram. By entering, you confirm over 18+ years of age, release Instagram of responsability, and agree to Instagram's terms of use.

#TailwindAir #KimberlyPucci #Flythefastlane #giveaway #manhattan #boston #nyc #newyork #flights #bags

It's your time to win!🎉

From this January 30th through February 15th, Tailwind Air and its partner, Kimberly Pucci, are teaming up to offer our customers a sensational prize: win a round trip to Manhattan or Boston during the 2023 season, plus a KP gorgeous purse!

Prize value:
KP weekender $2100
Tailwind flight $3100
Total: $5200

What do you have to do to participate?👇

1️⃣ Mention 3 friends.
2️⃣ Follow @kimberly.pucci and us.
3️⃣ Like this post.
4️⃣ Share in stories and tag us.

Make sure you follow all FOUR steps.

The winner will be announced on 02/17 at 4 PM via TW Instagram.🏆

Please note flights must be booked for march, 2023.
No purchase necessary to enter Sweepstake.
Terms and conditions apply.
The winner must be located in the US.⁠

It's simple, so participate and have a great year by flying the fast lane!

This promotion is in no way sponsored, administered, or associated with Instagram. By entering, you confirm over 18+ years of age, release Instagram of responsability, and agree to Instagram's terms of use.

#TailwindAir #KimberlyPucci #Flythefastlane #giveaway #manhattan #boston #nyc #newyork #flights #bags
...

Are you already participating?👌 This morning, Are you already participating?👌

This morning, @cheddar shared the good news about our Treat Yourself Sweepstakes with @mo_boston, and you can be the lucky one who enjoys this unique prize. 

Give yourself a chance to win!🎉

#TreatYourselfwithCheddar #CheddarGiveaway #tailwindair #mandarinorientalboston #Boston #NYC #giveaway #travelers #charters #seaplanes #travel #flythefastlane

Are you already participating?👌

This morning, @cheddar shared the good news about our Treat Yourself Sweepstakes with @mo_boston, and you can be the lucky one who enjoys this unique prize.

Give yourself a chance to win!🎉

#TreatYourselfwithCheddar #CheddarGiveaway #tailwindair #mandarinorientalboston #Boston #NYC #giveaway #travelers #charters #seaplanes #travel #flythefastlane
...

Treat Yourself Sweepstakes! 💫 You will have th Treat Yourself Sweepstakes! 💫

You will have the opportunity to be the winner of a Seaplane trip by @tailwindair from NYC to Boston + a One-night hotel stay at @mo_boston. 

Stay tuned this January 27th at @Cheddar Show between 7 AM - 10 AM to get the secret word, fill in their info to participate, and win this huge prize.  Link in the bio.

Your chance to win awaits!🎉

#TreatYourselfwithCheddar #CheddarGiveaway #tailwindair #mandarinorientalboston #Boston #NYC #giveaway #travelers #charters #seaplanes #travel #flythefastlane

Treat Yourself Sweepstakes! 💫

You will have the opportunity to be the winner of a Seaplane trip by @tailwindair from NYC to Boston + a One-night hotel stay at @mo_boston.

Stay tuned this January 27th at @Cheddar Show between 7 AM - 10 AM to get the secret word, fill in their info to participate, and win this huge prize. Link in the bio.

Your chance to win awaits!🎉

#TreatYourselfwithCheddar #CheddarGiveaway #tailwindair #mandarinorientalboston #Boston #NYC #giveaway #travelers #charters #seaplanes #travel #flythefastlane
...

The Big Apple is waiting for you!🗽 New York is The Big Apple is waiting for you!🗽

New York is a unique city, with lots of diversity and always at the forefront, and everyone wants to experience it. 

If you don't know where to begin, here are some ideas when you get to the city that never sleeps.

Book your flight with the fast lane.✨

#tailwindair #flytailwind #flytailwindair #NY #TheBigApple #Manhattan #travelers #travel #shuttleservice #seaplanes #jets #charters

The Big Apple is waiting for you!🗽

New York is a unique city, with lots of diversity and always at the forefront, and everyone wants to experience it.

If you don't know where to begin, here are some ideas when you get to the city that never sleeps.

Book your flight with the fast lane.✨

#tailwindair #flytailwind #flytailwindair #NY #TheBigApple #Manhattan #travelers #travel #shuttleservice #seaplanes #jets #charters
...

We joined forces with @Cheddar for the ultimate Tr We joined forces with @Cheddar for the ultimate Treat Yourself giveaway!🤩 

Watch Wake up with Cheddar  to get the secret word and enter to win a huge prize giveaway!

Potential winners can participate in the giveaway by filling in their info and a secret word that will be revealed on our Wake Up with Cheddar show. Link in bio.👌

Good luck to everyone.✨

#TreatYourselfwithCheddar #CheddarGiveaway #tailwindair #giveaway #travelers #charters #seaplanes #travel #flythefastlane

We joined forces with @Cheddar for the ultimate Treat Yourself giveaway!🤩

Watch Wake up with Cheddar to get the secret word and enter to win a huge prize giveaway!

Potential winners can participate in the giveaway by filling in their info and a secret word that will be revealed on our Wake Up with Cheddar show. Link in bio.👌

Good luck to everyone.✨

#TreatYourselfwithCheddar #CheddarGiveaway #tailwindair #giveaway #travelers #charters #seaplanes #travel #flythefastlane
...

Do you want the Tailwind experience? ✨ That's al Do you want the Tailwind experience? ✨ That's all you need to fly with us because we are happy to get you to your favorite destinations!

Plan your travel, book through flytailwind.com and have a Tailwind experience to remember.

#tailwindair #flytailwind #flytailwindair #flythefastlane #tailwindexperience #destinations #travelers #travel #shuttleservice #seaplanes #jets #charters #charterflight

Do you want the Tailwind experience? ✨ That's all you need to fly with us because we are happy to get you to your favorite destinations!

Plan your travel, book through flytailwind.com and have a Tailwind experience to remember.

#tailwindair #flytailwind #flytailwindair #flythefastlane #tailwindexperience #destinations #travelers #travel #shuttleservice #seaplanes #jets #charters #charterflight
...

All your travel experiences should be enjoyable, a All your travel experiences should be enjoyable, and with @tailwindair we make sure you get the best.✨

Because there is no other way of traveling than the fast lane?

Book at flytailwind.com and fly better than first class.

#tailwindair #flytailwind #flytailwindair #flythefastlane #tailwindexperience #kimberlypucci #brandpartner #firstclass #luxury #elegance #destinations #travelers #travel #shuttleservice #seaplanes #jets #charters #charterflight

All your travel experiences should be enjoyable, and with @tailwindair we make sure you get the best.✨

Because there is no other way of traveling than the fast lane?

Book at flytailwind.com and fly better than first class.

#tailwindair #flytailwind #flytailwindair #flythefastlane #tailwindexperience #kimberlypucci #brandpartner #firstclass #luxury #elegance #destinations #travelers #travel #shuttleservice #seaplanes #jets #charters #charterflight
...

Travel as you deserve!💫 We always make the Tai Travel as you deserve!💫

We always make the Tailwind experience the best from start to finish. Fly the fast lane, and we will change your mind for sure.

Visit flytailwind.com and book your favorite destination.😁

#tailwindair #flytailwind #flytailwindair #flythefastlane #tailwindexperience #destinations #travelers #travel #shuttleservice #seaplanes #jets #charters #charterflight

Travel as you deserve!💫

We always make the Tailwind experience the best from start to finish. Fly the fast lane, and we will change your mind for sure.

Visit flytailwind.com and book your favorite destination.😁

#tailwindair #flytailwind #flytailwindair #flythefastlane #tailwindexperience #destinations #travelers #travel #shuttleservice #seaplanes #jets #charters #charterflight
...

Shopping, dining and entertainment. Sounds incredi Shopping, dining and entertainment. Sounds incredible, doesn't it?🤩

Make this a reality with our charter flights from Florida to our destinations!

But we want to hear from you, where would you go? Let's talk in the section comment.👇

#tailwindair #flytailwind #flytailwindair #flythefastlane #florida #bahamas #beach #thecaribbean #sun #travelers #travel #shuttleservice #seaplanes #jets #charters

Shopping, dining and entertainment. Sounds incredible, doesn't it?🤩

Make this a reality with our charter flights from Florida to our destinations!

But we want to hear from you, where would you go? Let's talk in the section comment.👇

#tailwindair #flytailwind #flytailwindair #flythefastlane #florida #bahamas #beach #thecaribbean #sun #travelers #travel #shuttleservice #seaplanes #jets #charters
...

The incredible moments stay with us forever.🙌 The incredible moments stay with us forever.🙌

Traveling is life-changing, allowing us to become enchanted by different places.

That's why we want to know your favorite trip, doesn't matter if it was alone, with friends, or with family. Don't be shy and talk below.👇

#tailwindair #flytailwind #flytailwindair #flythefastlane #florida #travel #beach #moments #experience #travelers #travel #shuttleservice #seaplanes #jets #charters

The incredible moments stay with us forever.🙌

Traveling is life-changing, allowing us to become enchanted by different places.

That's why we want to know your favorite trip, doesn't matter if it was alone, with friends, or with family. Don't be shy and talk below.👇

#tailwindair #flytailwind #flytailwindair #flythefastlane #florida #travel #beach #moments #experience #travelers #travel #shuttleservice #seaplanes #jets #charters
...

There are 700 islands in The Bahamas. With so many There are 700 islands in The Bahamas. With so many islands to explore, why not embark on a day excursion to discover Pearl Island, Ship Channel Cay, Rose Island, or the Exumas?🏝️

Check out the many boating and sailing excursions available from Nassau Paradise Island.

#tailwindair #flytailwind #flytailwindair #flythefastlane #bahamas #thebahamas #didyouknow #funfacts #travelers #travel #shuttleservice #seaplanes #jets #charters

There are 700 islands in The Bahamas. With so many islands to explore, why not embark on a day excursion to discover Pearl Island, Ship Channel Cay, Rose Island, or the Exumas?🏝️

Check out the many boating and sailing excursions available from Nassau Paradise Island.

#tailwindair #flytailwind #flytailwindair #flythefastlane #bahamas #thebahamas #didyouknow #funfacts #travelers #travel #shuttleservice #seaplanes #jets #charters
...

Enjoy the experience of trip adventures with the f Enjoy the experience of trip adventures with the fast lane next to your loved ones and create beautiful memories.💫

Take advantage of @tailwindair's flight booking service and select your destination.

#tailwindair #flytailwind #flytailwindair #travelers #travel #shuttleservice #seaplanes #jets #charters

Enjoy the experience of trip adventures with the fast lane next to your loved ones and create beautiful memories.💫

Take advantage of @tailwindair's flight booking service and select your destination.

#tailwindair #flytailwind #flytailwindair #travelers #travel #shuttleservice #seaplanes #jets #charters
...

Winter break planning!🏖️ Many places sound g Winter break planning!🏖️

Many places sound great to enjoy the sun by the ocean, and we want to know your must-see vacation destinations below, as many of them can be reached by our charter flights. 

Are you ready to have fun? Click on fly tailwind.com and answer all your questions.😁

#tailwindair #flytailwind #flytailwindair #flythefastlane #florida #bahamas #beach #thecaribbean #sun #travelers #travel #shuttleservice #seaplanes #jets #charters

Winter break planning!🏖️

Many places sound great to enjoy the sun by the ocean, and we want to know your must-see vacation destinations below, as many of them can be reached by our charter flights.

Are you ready to have fun? Click on fly tailwind.com and answer all your questions.😁

#tailwindair #flytailwind #flytailwindair #flythefastlane #florida #bahamas #beach #thecaribbean #sun #travelers #travel #shuttleservice #seaplanes #jets #charters
...

We have been preparing for you!😍 2023 will b We have been preparing for you!😍

2023 will be the year of knowing new destinations to be pleased with, and why not do it in time record?  Boston, Manhattan, and Washington will return in March 2023 for all of you.

Book your flight and fly the fast lane with @tailwindair 💫

#tailwindair #flytailwind #flytailwindair #Boston #Washington #Manhattan #travelers #travel #shuttleservice #seaplanes #jets #charters

We have been preparing for you!😍

2023 will be the year of knowing new destinations to be pleased with, and why not do it in time record? Boston, Manhattan, and Washington will return in March 2023 for all of you.

Book your flight and fly the fast lane with @tailwindair 💫

#tailwindair #flytailwind #flytailwindair #Boston #Washington #Manhattan #travelers #travel #shuttleservice #seaplanes #jets #charters
...

Have you been thinking about treating a friend to Have you been thinking about treating a friend to a fantastic experience? 🤩 If you buy any flight credit, you will receive a bonus credit added to your account. Also, receive a $300 gift certificate when you book any of our sightseeing charters.

Share the Tailwind experience with your buddies and fly the fast lane.

#tailwindair #flytailwind #flytailwindair #flythefastlane #giftcard #discount #friends #travelers #travel #shuttleservice #seaplanes #jets #charters

Have you been thinking about treating a friend to a fantastic experience? 🤩 If you buy any flight credit, you will receive a bonus credit added to your account. Also, receive a $300 gift certificate when you book any of our sightseeing charters.

Share the Tailwind experience with your buddies and fly the fast lane.

#tailwindair #flytailwind #flytailwindair #flythefastlane #giftcard #discount #friends #travelers #travel #shuttleservice #seaplanes #jets #charters
...

It's a tough call, isn't it?🤔 Anywhere in Flor It's a tough call, isn't it?🤔

Anywhere in Florida is a great place to enjoy. Now is your chance! 

Same places? Why not try something new and book The Bahamas?🏖️

A popular place for travelers because of its beautiful beaches, tranquility, and excellent service wherever they stay!

Pick one, travel with Tailwind Air, and have the experience of a lifetime!🤩

#tailwindair #flytailwind #flytailwindair #flythefastlane #florida #bahamas #beach #thecaribbean #sun #travelers #travel #shuttleservice #seaplanes #jets #charters

It's a tough call, isn't it?🤔

Anywhere in Florida is a great place to enjoy. Now is your chance!

Same places? Why not try something new and book The Bahamas?🏖️

A popular place for travelers because of its beautiful beaches, tranquility, and excellent service wherever they stay!

Pick one, travel with Tailwind Air, and have the experience of a lifetime!🤩

#tailwindair #flytailwind #flytailwindair #flythefastlane #florida #bahamas #beach #thecaribbean #sun #travelers #travel #shuttleservice #seaplanes #jets #charters
...

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.

through our partner iflysouthern.com

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