Having 2 rooms seems a little bit of an extravagance to me (unless 1 of them is in the Hotel Asia

) although it is certainly one way to go. Personally, I'd rather spend that extra $50+ on chicas. Decide what you are going to do. If you are going to stick with the pros and semi-pros, you might as well stay where the action is. If one night you secure a date with a non-pro, you can still change hotels for that night or get a second room. Thats what I had to do one time between the DR and the Don Carlos. But you can also pick a hotel that reasonably serves both needs. There are several hotels that border the gulch (rather than being in the very belly of the beast) that are fairly chica friendly. The Don Carlos and the Castillo are two that come to mind. You will have to share the hotel with families and eco-tourists so you will need to tone down your act and multiple guests each night are out, but you are still within walking distance or a very short cab from the action. In the case of the 2 previously mentioned hotels you are actually closer to ZB, NF and El Pueblo. If scoring non-pros will be your primary pursuit than hotels farther afield begin to make more sense. You could also choose someplace like the BW Irazu, which would be particularly good if you plan to do your hunting in Escazu. OTOH, the Casa Conde is much closer to downtown and the University at San Pedro and will definitely impress your date a lot more.