Flying Private

First-class is so yesterday. True big spenders know that the only real way to travel is private—and lucky for us, Westchester County Airport (HPN) has plenty of private aviation options that will keep you away from the flying masses.

Swank Shuttle

The Signature Shuttle service from Tradewind Aviation (above)—which is based in Oxford, Connecticut, but offers flights from HPN—offers travelers private charter perks (no TSA security checkpoints, private gate entrance, exclusive lounges, complimentary on-board drinks, and checked baggage) for the cost of a single seat. Where will it take you? Shuttles are available from HPN to Boston (starts at $395 per one-way ticket) and Stowe, Vermont (starts at $350 per one-way ticket), year-round; to Nantucket (starts at $585 per one-way ticket) and Martha’s Vineyard (starts at $545 per one-way ticket) during summer months.

Tradewind Aviation (800) 376-7922

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Imagine That

Discounted on-demand private-jet service ImagineAir, headquartered in Atlanta, entered the Westchester market two years ago. Its three-passenger aircrafts (all Cirrus SR22s) can be yours for an average price of $1,200 (typical private-jet rental is closer to $7,500). They currently service more than 1,000 airports in the Eastern US, but our favorite trip is one they put together just for us: Hop a flight from HPN to Nantucket and experience a complimentary ultra-personalized culinary and cocktail adventure at Nantucket’s award-winning Nautilus Restaurant. The package includes the flight, a welcome glass of wine, private tour of the Nautilus, a cocktail demonstration and tasting, and a multi-course, small-plate-centric dinner. 

ImagineAir (877) 359-4242 

Flex Your Muscle 

Flexjet LLC’s Red Label program is the very definition of the luxury fractional-ownership experience: call one number to schedule a flight and your account team will coordinate everything else, from transportation to high-end catering. Flexjet’s fractional and lease options work like a timeshare, purchased in 50-hour increments with a 30- to 60-month contract commitment. A 1/16th share is Flexjet’s most commonly purchased share and grants owners access to 50 annual hours in an aircraft. Figure on an all-in cost (includes the cost of acquiring the fractional share, a monthly management fee, and the occupied hourly rate that covers the direct costs of operating the aircraft) of about $5,000 an hour.  You can also opt for the Jet Card, purchased in 25-hour increments with no contract commitment. Flexjet currently offers flights from HPN and is aiming to establish its own private terminal at the airport later this year.

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Flexjet (866) 473-0025

More Options: 

Charter a private flight via Million Air ( from HPN to Florida, the Bahamas or the Caribbean, starting at $15,000…Purchase a membership with JetSmarter ( for $9,000 per year for unlimited access to private flights from HPN… Helicopter more your style? Wings Air (, based at HPN, flies charter to destinations within 300 miles, including the Hamptons and Atlantic City, starting at $2,900 each way. 


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