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What do you guys do to make sure every flight is a learning experience?
(aside from "I learned about flying from that" stories, which I'd
prefer to read about rather than re-enact.)

Personally, I don't go out of my way to "make sure every flight is a
learning experience". Many flights are, of course. But every flight should
be planned with the goal of the flight taking place exactly as planned,
without any surprises. And then you should actually fly the flight as if
nothing will go according to plan, so that you are always ready to fix the
plan to accomodate the new situation.

Now, that said, you have a very specific flight in mind, and I think it's
reasonable to look for ways to make it more interesting. I don't think it's
rocket science though. You can probably come up with most, if not all, of
the various ways yourself.

Some strategies that might be helpful:

* Make one of your landings at an airport that appears to be especially
hard to find. Of course, they all look easy on the chart, but a short
runway (not shorter than you can safely manage, of course) is often more
difficult, as are airports without lots of services or based aircraft
(airports are harder to find if there aren't a bunch of airplanes sitting
around on the ground ).

* Route your flight through various kinds of airspace requiring contact
with ATC. Use VFR flight following. Use a VFR flight plan.

* Challenge yourself to use the available weather information to verify
and/or correct the winds aloft forecast. For extra credit, use this
information along with your suggestion of doing some dead reckoning. See
how close to the mark you get.

* Practice your pilotage. Dead reckoning is fine, but for VFR flight
pilotage is where it's at. It's something you can use on every single
flight if you want to, and it is lots of fun.

* Actually get out at one of your stops. Try to get a meal. Fill up
the airplane's gas tanks. You may have already done this many times, but
personally I have found that the elements of flight between takeoff and
landing tend to be very similar. It's when you get to your destination that
every trip is different. For extra credit, see how close to your actual
fuel burn you can get with your calculations.

* Find a place to land that's unusual, even beyond being hard to find.
Here in the Pacific Northwest, Copalis Beach (a "runway" on the sand) is a
new experience for many. Near Los Angeles, landing on Catalina Island can
be a fun, but reasonably safe challenge (though, I haven't heard a report on
the pavement conditions in awhile). I don't know where your flight is
likely to take you, but surely there's an airport or two around that is
particularly unusual, even beyond some specific dimensional characteristic.

Most of all, just have fun. Frankly, while I can definitely relate to the
"having friends along is more fun", I think you're missing out if you don't
do a good long flight solo once in awhile. For me, it's about as far as I
can get from the real world. I have the whole plane to myself. No one is
expecting me to chat with them. The headsets keep the airplane noise down,
and otherwise my experience is completely silent. Obviously this works
better if you don't have to talk to ATC, but I've found that especially for
VFR flights, the occasional need to talk on the radio doesn't negate the
great "wakeful meditation" that solo flight provides.

Beyond any suggestion for making the flight more challenging or interesting,
simply take advantage of this rare opportunity to experience flight in a
completely new way. A way that you are not accustomed to experiencing,
since you always work so hard to bring someone else along. It's not bad.
It's just different.

Pete