Wing It is a Facebook Messenger bot that tries to get you out of that rut. You punch in your criteria, and it’ll pop up every once in a while when it finds trips that fit the bill, recommending accommodations and an activity or two in the area. Wing It asks just a few questions off the bat: Where do you live? How far do you want to go? Is it just you and a partner, or a big group of friends? How much is each person looking to spend? A few minutes later, it’ll respond with a short list: a few places to stay and some things you might want to do while there. Right now, that’s mostly hikes and trails; eventually, the Wing It team hopes to expand their knowledge base out to things like kayaking trips, rock climbing, or nearby surf spots.