Sarah Milstein, Boing Boing's chief loop closer, has a piece in the New York Times about "urban hiking" — a way to get exercise and socialize at the same time.
Plan your route, and – this is going to sound crazy – assume you'll go a mile or maybe two an hour. With a group, you'll move a lot more slowly than you expect. We usually aim for about five miles (www.gmap-pedometer.com is good for figuring out distances) and include about six points of interest and two takeout food stops. To allow for lots of conversation, keep your highlights farther apart than the typical walking tour and mostly brief. (If your group includes strollers and dogs, don't forget to plan a route that will work for them.)
