In Rome, you HAVE to eat at Alfredo alla Scrofa. They claim to be the originator of Fettucinni Alfredo, and the way it tastes, I'm not going to doubt them. I've only been during lunch, usually not too crowded, I'm sure their dinner service is packed. Bit pricey, 20 euro for the Fettucinni, but well worth it. Also, I wouldn't recommend the whole "we'll split one and try something else" thing, you'll both want one lol.
If you're in Italy in July/August then Rimini is a good spot, small beach town with a little kick to it. It's the Italian version of like Miami. Jammin Hostel is like 3 blocks from the beach, and 2 from the main strip.
Then there is Thailand, you can tell Raes he can have a cheat, but you want to set it up. Then find a lady boy for him! But Full Moon Party in Koh Phangan is off the hook, and the neighbor island, Koh Samui, has a small island on the north side that you can actually walk to because of a sandbar.
I need to hit Brazil for sure, but it has to be at Carnival or I wont feel right.