Friends don't let friends plan bad trips
When traveling to a new city it can be hard to find trustworthy advice, unless that city happens to be New York, Los Angeles, Chicago, Boston, Philadelphia, San Francisco, Seattle, Miami, Portland, San Diego, Austin, London, Atlanta, Dallas, DC, Minneapolis, Denver, Las Vegas, or the Hamptons between May and August. For places where even Thrillist can't make you look awesome, there's Trippy.
Still in private beta, Trippy'll build you a personalized itinerary based on the most reliable sources by harnessing the knowledge of Facebook contacts who've got a connection to your destination, assuming they're friend-ly enough to bother helping you out.
Enter any trip dates & the type of visit you prefer (e.g., Family, Budget, Adventure), briefly describe what would make a "great" trip, and add any spots you're already planning to visit, and it'll build out a tentative itinerary, likely to become a more outgoing itinerary once you hit all those bars on it.
Next it'll scour those F-book contacts and create a list of anyone who lives/grew up/studied abroad there, letting you tap whom you're comfortable requesting help from via a message with a link to your itinerary; their suggestions'll show up in your Recommendations section, and can be either slotted into your daily planner or ignored like "If you liked Stealing Harvard, you might also like Steel Magnolias".
You can also manage your itinerary and upload pics/vids on-the-go thanks to their nifty iPhone app, which is something a certain daily email also has if you happen to be going to New York, Los Angeles, Chicago, Boston, Philadelphia, San Francisco, Seattle, Miami, Portland, San Diego...