Let me preface this nonsensical travelogue by saying that if you absolutely must travel overseas, or anywhere really, do so on someone else's bankroll. Be it parents, dirty money or through other means, be sure someone else fronts your likely plush and extravagant bill because Europe can be one expensive beast of a place.
First, a quick tutorial to prepare you. Avoid driving. Walking is inexpensive and generally the easiest way to travel. Use a taxi, particularly if you have to get to and from your transportation areas (train stations, airports, teleports).
Also, the Euro is stronger than the dollar (thanks W) and often pushes the dollar to its knees and steals its juicebox, so be forewarned. Something that is 20 Euros and seems like a good deal may actually be, but just realize that currently it's more like 26 or 27 dollars, more or less.
Next, eating is an experience in Italy. Regarding appetizers (antipasti), Italians don't understand sharing one appetizer per table and with just cause (the portions are moderately-sized). So, at a restaurant, everyone can order an appetizer and share (they prefer it that way, really) and it won't be overkill.
Also, don't be surprised if the bill takes an inordinate amount of time to come. In fact, you will often have to request it. Once you're there, you're family (you know, like the Olive Garden claims). However, unlike the Olive Garden, they are serious. Stay as long as you like, they don't mind. Their hours are flexible. So, eat, drink, be happy and enjoy yourself - you're in Italy, you crazy fool.
When in Rome...
Venice the menace
Venice is a magical, wonderful and populated (read: touristy) city that is good for brief, mostly intoxicated or sunstroked stints. Yes, like the Vegas of Italy. While there, be sure to check out the Peggy Guggenheim Collection, where you'll see some of modern art's finest masterpieces by Ernst, Magritte and ol' Picasso.
While it's certainly fun to watch dozens of folks laugh and giggle as handfuls of diseased rats with wings cover their arms and heads, I decided to keep a safe distance from feeding the pigeons in Piazza San Marco (home of the famous Basilica di San Marco).
The seafood in Venice is wonderful and worth the price of admission alone (you don't actually have to pay to be admitted to restaurants in Italy, don't be a victim!). While your meal -- which should for posterity's sake contain some sort of shelled or antennaed crustacean -- may be delicious, be wary of a seemingly pleasant sounding post-meal glass of Limoncello. In truth, the lemon liquor will scramble your brain and judgment, making your wonderful meal more of a distant hallucination. Tasty though.
Speaking of ruining your life, perhaps the most famous bar throughout Italy (Rome, Florence, Venice) is Harry's Bar. It's famous for being Ernest Hemingway's favorite spot to pickle his liver and has spawned imitators across the world. However, the one in Venice, along the Grand Canal, is the original and my personal recommendation for "Bar to done get sloppy in." The bar makes traditional, old school drinks that would wet the whistle of any Rat Packer and even serves food, which I hear is so-so.
Tune in next week for the (not so) thrilling conclusion of my adventures on foreign turf...