okay, here we go. I stayed in Riomaggiore, which is the smallest and furthest from the central rail (La Spezia line) of the 5 towns. It looks like this:
there are little houses you can rent a room out of on the cheap (though i've been told it's slightly more expensive since i've been), which is definitely a way to meet total strangers and get drunk with them. They're not the most lavish accomadations, but it's easy to get you're own room and you really don't spend that much time there anyway. If this is a romantic trip, though, you might wanna shell out some more money for a hotel room, and it's wise to book those way in advance.
the town is small, a dozen or so shops, an internet cafe, and like 3 restaurants, all of which will knock you on your ass. Cinque Terra serves more seafood than anything ( what being an ocean town and all) so while there's still some great examples of what we think of as "Italian" food there, you'd be a fool not to try the fresh fish every night. Also, there is a specific white wine that is grown and harvested right in the villages that you should probably try. i don't like white wine so i stuck with red, but you get my point.
there isn't the largest of nightlifes in Riomaggiore, or any of the other towns for that matter. Everything closes down more or less by 11PM if not earlier. This is kinda nice because the massive church bells all over the town will wake you the fuck up early in the morning. Also, most of the travellers (being the young adventurous drunks that they are) usually load up on wine during the evening and then head to the beach a few hours after sundown. This was a lot of fun, and a great way to unwind and meet some random people.
the hike itself takes like 3-5 hours, so it's not very hard to cruise in a day, stopping for lunch or whatever in all the towns, check out the wu-tang graffiti in the tunnels, and take the train back to wherever you're staying. It's kinda of exhausting, and in october the orchards will probably be overflowing with something or another, but still worth the trek.
i could've stayed there for another whole week, i mean it really is gorgeous and people are absurdly friendly. For some reason they're nuts about tom cruise there, buit otherwise they're a sweet and rational people who are more than willing to tell you what they're thinking and invite you to eat at their table. Granted, I went in september and while the tourist season was still very much on (germans EVERYWHERE), I can't honestly say what it's like in october. If you're looking more to party I don't know how much of it you'll find in Riomaggiore, but i'm sure there's always some sort of crowd there.
this is all i'm thinking of right now, but if you have any questions don't be shy with 'em, because i'm sure i'm forgetting alot of it.
this link is a nice little idea of the joint.
as far as the other places,
Rome can be a blast, but it really depends on who you're with, where you go, and how you feel about men on scooters with flourescent yellow backpacks.
Venice is MUY overrated. Great historical sites, but little else. the gondola rides are fucking stupid unless you're a complete retard and in love with another one. I didn't like Milan too much, but i was only there 2 days. I didn't get a chance to tour florence, regretably. These all paled to the smaller towns IMO. Orvieto and Lake Garda were places I fell in love with right away and everyone i know that's been there says the ssame. Those and Cinque Terra are easily my favorite places in Italy, though to be fair it's still Italy and you're probably gonna love it no matter where you end up.