After 4 years with a pilot's license, I took my first serious long-distance
trip, travelling for two weeks in a Grumman Tiger: me, a bicycle, and a few
bags. Went Boston - Nashville - Roanoke - Norfolk - Boston (actually
smaller airports near each of these places). Biggest thing I learned; your
itinerary is going to be determined more by the weather and the mechanical
state of your plane than by you - so you have to be flexible and be prepared
for things to take longer than planned.

I started having electrical problems on the trip between Murfreesboro, TN
(MBT) and Roanoke. Ended up stopping in Beckley, WV (BKW) after the battery
died. Got it recharged and the next day headed over the Appalachia, but
found my flight was blocked by low-lying clouds. Tried again an hour later
and this time it was clear enough to go over, but on the way I noticed my
ammeter was pegging negative. Turned out all the lights and other electrical
load and continued to Lynchburg (LYH) where it turns out I had a bad
alternator. So I had been flying over the mountains probably powered by
battery alone. While they were replacing the alternator it started to snow,
and it snowed for the next 3 days. So I rented a car, visited Monticello and
Appomatox, hung out in the hotel swimming pool, hung out in Barnes and
Noble. Got a lot of reading done......... But I still could not return to
Boston because it was snowing there. So I improvised and flew to Kitty Hawk
(20kt crosswind, so no landing), Cape Hatteras, and then to
Jamestown-Williamsburg (JGG), where I spent a day at colonial Williamsburg.
The return trip was fast; a 15~20kt tailwind pushed me from
Jamestown-Williamsburg back to Boston in less than 4 hours. Highlight was a
trip up the Hudson River VFR exclusion corridor. It was a little hazy so I
could not see Manhattan as I left the New Jersey shore but I just followed
the Colts Neck VOR out at a heading that would bring me to the
Verranzo-Narrows bridge and in about a minute it came into view. After that
it was just keeping the altitude below Class B and self-announcing on the
Hudson River frequency. 2pm on a Tuesday afternoon I guess is a good time to
go through, there was very little traffic, and after all my apprehension
about doing this for the first time it was rather anti-climactic. 2 or 3
helicopters; that was it - had to help one who could not see me and had to
climb to go over to LGA from the West 30th street heliport. When you are
close up to the buildings you really get a sense of how fast you are moving.
It was quick - less than 5 minutes and I was out the other side.

My other big impression - Eastern Kentucky. I had noticed on the chart that
there were very few airports, and was curious as to why. When I flew over it
was miles and miles of hills, strip mines, very small towns and little else.
Not many places to land in an emergency, it was rather spooky. I stayed up
at 7500~9500 for most of the trip, and was happy for the strong tailwind
that got my ground speed up to over 160 kts. and safely into Beckley, while
the whole time my battery was draining.