You could start off with some automation i.e. make a crawler. Start with seeds from top rated places from Yelp, Gowalla, etc. Then, blast your queries across so

You could start off with some automation i.e. make a crawler. Start with seeds from top rated places from Yelp, Gowalla, etc. Then, blast your queries across some travel site APIs and freebase.com to see what kinds of interesting places you get. Then, you can perhaps do model based collaborative filtering and do the recommendations automatically. Or for inspiration... http://www.tripbase.com http://www.tripbase.com