I like old countries, so I haven't much explored Canada or the U.S. My last major trip overseas was to Rome, Italy as we figured that when it comes to ancient history (art and architecture) it's hard to beat starting off with a city that boasts the Coliseum, the Pantheon and the Vatican.
We flew into Da Vinci airport (because really, what else would they call it) and took a forgettable 1.5 hour bus ride into Rome, with the bus stopping at each major hotel in turn to deposit some occupants. We were second last, having gone with a nice hotel but one on the perimeter of the city. I'd actually recommend going this route as long as there's a fairly decent bus route running nearby; there's no reason to pay inflated prices to be closer to major landmarks. I'm big on using public transit whenever I travel - Rome's subway system is pretty small compared to other famous cities, but its bus service makes up for it. The buses are on the honour system, so like the locals, more often than not we "forgot" to pay our fare.
Last word on the subject of inter-city travel: Crossing roads on foot in Rome was frightening as cars stopping at crosswalks do not actually stop until a pedestrian is, in fact, crossing right in front of them. This turns into a minor game of chicken as cars continue at full speed until some courageous fellow (usually a local, with a bunch of us tourists quickly skittering along behind them) blindly walks out in front of them. I've seen worse (in Karachi, so that's bottom of the barrel stuff) and nobody I saw actually got injured, so maybe it's not as bad as it looks. You can get used to anything, though: Two or three days in and we were braving traffic like a native Roman.
Being late risers due to being on vacation and always getting to bed quite late, we generally starved during the day as most restaurants only open after 7 or 8 PM in the evening. Once they're open, though, they're in it for the long haul: We ate on a couple of piazzas where we sat down at 10 PM or so and left at, oh, 1 AM? The staff was still going strong; eating hours there seem to be shifted forward by something like four hours. And while you don't have to, we did heavily indulge in pasta, pizza and wine while in Rome. This led to us invariably being tipsy by the end of the night, walking or taking a bus back to the hotel, changing into our swimwear and then breaking the rules to make use of the hotel's rooftop pool long after its midnight closing. This is when I discovered that the feeling uncomfortably full is 100% countered by jumping into a cold pool while being half drunk. Literally worked every time.
The food and nightlife inside Rome proper is actually pretty bland in our experience; the city really only has tourists walking around in it after it gets dark as it appears that the locals all live and play in the suburbs. It's here that staying in a hotel on the outskirts turned to our advantage - we ventured back to near the Parthenon for a few meals, but the majority of them were taken in trattorias in the suburbs. We ingratiated ourselves in one or two places and got terrific value for our Euro out there, but even so when Saturday night rolled around we couldn't find a seat in a decent restaurant anywhere we went. Every seat was unofficially reserved for the extended families of locals, who came out in groups of fifteen or twenty and sat down at large tables where the youngest was at one end and grandma or grandpa were at the other. They were clearly in the pattern of doing this every Saturday since who knows when and only by haggling for an extra two chairs and to sit way out to the side did we get service that night.
Dining with the locals involved lots of chatter, lots of smoking (second-hand smoke is a real concern if you worry about things like that), lots of wine, and truly stupendous amounts of food consumed. I'm not sure how locals manage to have olives for starters, pasta as a first main course, pizza as the second main, gelato for dessert and a bottle of wine accompanying all of the above. It's just too much - and yet somehow people appear to stay thin. (I think this is because TV isn't heavily watched and Internet access is unreliable, so it forces people outside. Or maybe everyone is a bulimic.) A note: All the starch in my diet made me feel vaguely ill for the duration of the trip so watch out for that.
Let me wrap this up with pictures and some quick notes about landmarks: The inside of the St. Peter's Basilica in the Vatican was magnificent for the sheer size of the place, but really what left me feeling stunned was to walk into the Pantheon, the first and oldest domed roof building in the world, and to stand in the spot in which the hole in the roof allowed sun in. Only a small step down from that was the realization that the remains of Raphael were in the building. Aside from that, I thought that the art in the Vatican was easily bested by the art found in Borghese Gallery up north in the Villa Borghese (a pain to get to, but worth the taxicab fare).
Weird thing about art in Italy: There's no velvet rope or protective glass up in front of any of it. You can press your nose to a Caravaggio if you feel like it. You should probably be shot if you do, but the option is there. My working theory is that Romans have been surrounded by ancient works for so long that it's faded into the background for them; it's not a big deal to be specially protected.
We were in Rome for nine days, which was probably about two days too long. Next up this December will be Hong Kong, and then hopefully Greece.