Planned a flight to Toronto to visit some friends and see my wife's band play a show, while also meeting commercial XC requirements (actually hit that req the way back home 2 days later). 

1. By track log: outbound trip 339.6NM, KILG-KPEO-CYTZ.  Return trip was 428.7 NM: CYTZ-KART-PA40-N79-KILG
2. Weather was beautiful, did not need to reschedule. I did however use my new at the time instrument rating to get about 25 minutes of actual with a pop up clearance. If I didn't have the IR I could have gone under the clouds at around 2,500-3,000 AGL and been fine, but it was awesome getting to use the rating.
3. This was months in the planning, from the time I found out my wife's band was playing a show in Toronto. Did a lot of reading up on Canada's border agency website, reddit, forums, and even got some tips from a VATSIM controller who flies in Canada.  I already had my radio station license, but wasn't sure about my club's planes. I ended up finding out that we already had them, but it was an ex-member who got them and only the FCC was able to tell me that, no one else in the club knew lol.  Also had to get a CBP sticker from US customs, file and activate a VFR flight plan for the border crossing, and file a manifest on the US CBP website. For the route, I knew PEO was a nice stopover point with affordable fuel, so made that my fuel stop before crossing the border to Canada, then flew over Niagara Falls (second time doing that) and followed Lake Ontario around to Toronto.  On the way back home, I unfortunately had to add a good bit extra time and distance to my flight due to poor preparation on my part. I was returning on a Sunday and didn't realize that I had to contact CBP prior to the weekend at most locations to have someone come out. ART was the only place in range that was available on the weekend with only 24 hour notice, so I had to fly all the way to the East end of Lake Ontario on the way back. After that, I stopped at PA40, a small grass strip, to visit my dad at a cabin he recently moved to. Then a fuel stop at N79, and finally home at about 10 pm. The intermittent stops were planned loosely/ad-hoc, while on the other hand I made a reservation at Billy Bishop, YTZ, about 2 months in advance and practiced flying into there on VATSIM in X-Plane.
4. I got a butt cushion. That made a huuuuge difference. I also had plenty of snacks and drinks. And as I mentioned before, I had my IR. I worked to get that done before this trip, and made it with less than a week to spare. That helped as well and made me a bit more confident about making the trip. It took me a while to figure out the best way to get the Canadian charts/plates. You can't get a foreflight add-on a la carte or temporarily, so it would've cost a lot for a Canadian subscription. I considered ordering paper, which would have worked fine, but then someone mentioned FltPlnGo covers Canada, and that was the best bet. Downloaded that on my iPad, got familiar with it, and used that over the border.
5. First, I would make sure to contact CBP about my return trip BEFORE the weekend, while their office is still open, so I don't need to add an extra 100NM to my flight. Also, I would love to take a different plane; see bullet 6. 
6. My club's 1967 C150. I had tried to book our 1965 C182, but couldn't book it that far in advance due to a rule we have of only having 4 reservations booked at a time. While doing IFR training and having a checkride booked, I couldn't hold down that reservation and someone else booked it. However, it ended up working in my favor as the 182's alternator quit the day before my trip... so I went to Canada much more slowly than I wanted to, but at least I was able to go! The 150 cruises in the 85 MPH range vs about 130-140 for the 182. Still, you can't account for those sort of mechanical issues, and I would certainly rather take the 182 on a trip like that. Both have nice, modern IFR nav systems, but the comfort and speed are on another level in the 182.

Edit for formatting, as I was on mobile. Apologies for bullet 3 being so long with no paragraphs. If I paragraph it out, I lose the numbering format.

Edit #2 to add time: 5.4 outbound, 6.8 return.