Just a short hop
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Every so often, a question comes into the PIC that has multiple answers, and has us, quite literally, shaking our heads. One such question came in this morning. I have set the stage as it was presented in the email:

The flight instructor is based at Cape Cod Gateway (HYA). The student pilot is based at Nantucket Memorial (ACK). The airports are 27 miles apart as the seagull flies. The student is ready for his night flying. The question posed by the flight instructor was - Can I sign him off to fly solo from HYA to ACK at night after completing his night XC?

I will share my response later, but for now, I am curious what answer(s) and/or advice you would give the instructor.
 

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@Daddis At AOPA
Not enough information presented.

Does the student own his own airplane?  Or is he renting from a flight school where the instructor is based?

If he owns his own airplane, is it based at HYA or ACK?

Is he just about ready for the practical and only needs night to finish up?

61.87(o) addresses night for students.  In 61.87(o)(1) it mentions the “airport where the solo flight will be conducted", not “the airports”.  In 61.87(o)(2), it requires “Navigation training at night in the vicinity of the airport”.  Use of the term “vicinity” suggest that cross country is not contemplated.

The regulation appears to not allow it and even if it did, I can't think of a compelling reason to do it.

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@Daddis At AO
Legally, yes, it's possible, but it will take a lot of training and endorsements, including either a new solo 61.93(c)(3) XC planning endorsement for each flight or the 61.93(b)(2) for repeated cross-countries within 50nm, as well as the 61.87(o) night solo endorsement.  There's nothing specifically addressing night solo XC's, so I don't see a prohibition, just the need to address each of the various components of a night solo XC I mentioned above.  There's also the issue of whether you can get the insurance company to buy off on this, but that's not an FAA issue.

And as Kris said, there's no compelling reason to do this.  If it's the student's airplane and it's based at HYA, and I was asked to get involved, I'd tell the student I'd drive to HYA to do the training out of there landing back there, and then drive home after the flight – with charges for my time and mileage.

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@Ronald Levy
in case it is not clear (since there has been a suggestion to drive from HYA to ACK) the two airports are separated by about 27 miles of Atlantic Ocean. Which introduces a new factor of having a student pilot fly at night over water with no ground reference. (JFK Jr?)

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@Paul Brock
 

@Ronald Levy
(JFK Jr?)

JFK Jr was about 50 hours into his instrument rating training.  He had substantial night training including flights to and ILS approaches at MVY.  One would expect better of someone with that much instrument and night training.  For  details, see:

But yes, I'd say doing that with a Student Pilot would be unwise, to put it mildly.

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@Paul Brock was thinking the same as me on this one.

All legalities and endorsements aside, if you pick up a Sectional and look at that route, you will see the plan was to send an inexperienced pilot with 25 hours, no instrument rating, minimal night-time logged, and very little, if any, instrument flying practice, over the featureless black void of the Nantucket Sound, under a nighttime sky. Not my idea of a smart plan…and that is how the instructor was advised.