Help with my website (Craigslist format)

So today I thought of something new that I'm going to try. I have an idea that has to do with travel, but it only focuses on a certain group of people. Anyways, I want to cover different cities and the only thing I can think of that comes close, is the way CraigsList is setup. So let's say this group of people were planning a trip, they could click on Los Angeles, CA and everything they need to know would be there. I'm going to start out with the most poplular areas this group goes to and branch out. Then I thought of contacting hotels and restaraunts in that area, to see if they want to advertise on my site. That is down the line though and I'm just starting this. My question is, how to build my website to cover the different cities. I'm a newbie to this and I keep thinking about pages on websites and that could get a bit too much. Is there a better way? I want to also include travel gear specialized for this group. So I have different pages in my head, I just don't know how to make the different cities work. I appreciate your help.