Is there a web travel site where you can pay a local to show you around?

Generally you would just contact a travel agency, or tour agency. I used to be a tour escort, and very often the ‘tour’ would be one person.

couchsurfing.com is mainly for finding places to stay but i think there is also an option for finding someone to show you around and tell you a little about the town.

You could try rent-a-friend or rent-a-local-friend. Haven’t tried them myself, so I can’t say how good they are.

There’s this woman in NY… I can’t think of her name, her daughter is a famous actress (someone help me out here!!!) but she will take a group of people around and to various restaurants in NYC, you choose which areas you want to go to…

If you’re in SF, I’ll take you around for pay!!! ;)

When I was in Rome, luckily I found a taxi driver who drove us all around town and told us everything he knew about Rome. Wasn’t that expensive and he took us around about half of the day.

I did the same thing in Trinidad & Tobago.

I suggest you only use a reputable tour agency.