Just had this idea came in mind, where you can find great pictures, activities and stories etc online, collect them together, and group them based on location(eg. neighbourhood, city or country? I'm planning my trip to Europe right now, and that seems the best way to organize everything together. I wonder if such service exists?
Whether intuitive or not depends on the person using it. I'm not really liking them much because every single one of them is too limiting in some way, not having the scale to be really useful outside of very popular destinations. Still, scores of people use the sites listed below, so perhaps you might like one of these as well:
Not really matching what you are asking, but what I find the best resource in this context is http://tripadvisor.com.
Maybe not quite what you're looking for, but have you tried Google Maps Engine? It's a very slick and featureful map creation service that lets you leverage the existing power of Google Maps and Google Places. Every time I go on a trip, I make a map with all the parks, museums, hostels, restaurants, etc. that I want to visit. Here's a recent (simple) example from Montreal.
You can try http://www.holidayen.com/. It's intuitive and you can get personalized recommendations on sights and activities, check out location and photos, create a daily itinerary and share your trip with friends as well. [Disclaimer: I work here]
You can also check out Awespot. This looks a lot like what you describe but mainly for places to visit and photos. You can browse all the places on a map of the world and check out photos at random.
Disclaimer: I do work on this website.