The bike tour with Joe was truly magnificent. My family and I bicycle in Florida and are used to risking our lives in crazy traffic next to distracted drivers, without protected bike lanes. The tour in DC was a breeze without any murderous moments. I wanted to move there about an hour into the tour. If you are used to cycling, this tour won't be exercise, but it will be fun. The bicycle allows for efficient sightseeing. I don't think you could see that many monuments from a bus or walking in the same period of time. I regret not having a set a timer on my phone for the pauses when the guide allowed us to experience on our own one monument and another. My older kid and I had some out-of-time relaxation and did not do a good job watching the clock. Pro tip: use an alarm. We packed a helmet for our toddler out of fear that the tour company wasn't really going to be prepared for someone so young, but we probably didn't need to bother. The company has a range of equipment, including Burley trailers. The tour guide seemed to be impressed with our seven-year-old's skill on a bike, so perhaps some families do not bike much before this tour. I think you will be fine without much experience, because most of it is flat or downhill. I never switched gears. I would bring water, if you can remember. (We forgot.) The sun was really strong on our tour, and I have to wonder if it wouldn't make more sense to start it about two hours earlier. Obviously, none of DC is set up for the way actual children function, so this musing is kind of gratuitous. The museums and tours all seem to start at 10 am, which is about one hour before naptime for some of the customers, but your child will enjoy sleeping in the trailer as much as mine did: short nap, owing to the zonked head bobbing, but a nap nonetheless. Joe recommended Potbelly's for lunch. I was doubtful that a chain was a great idea, but he was right. We ended up eating at a Potbelly's twice in DC, and it turns out that not all have the great kid's menu like the location near the bike tour, just FYI. Joe is right about the kid's shake. Ours loved it.