You absolutely should be skilled on a bike to do this ride. I have an e-bike I ride at home a lot and this was challenging for me and I often felt like I was not skilled enough to be doing it. It made me wonder if anyone ever has second thoughts and turns around. There is a lot of riding on narrow streets with other cars (and even buses) and while others said they got used to it with time, that wasn't the case for me. I was scared much of the time. And at the end, when you are tired, you are riding through the city with pedestrians, other cyclists, and traffic too. I also think people should know that we were gone from 10:30 until 4:30, with about 90 minutes spent at the winery and the rest of the time riding. I'm not sure how many miles total it is but it's a lot and these bikes are pedal assist that require you to pedal to get the boost and there is no throttle with the ability to "coast" like on newer e-bikes. The ride is very hilly and while the bikes did okay going up, going down some of the steep hills (there is one right after you leave the winery) was kind of scary to me.
The quieter parts of the ride and the parts on a true bike path were lovely. And the winery is a fabulous resting spot. The two of us shared a platter and probably should have gotten one for each of us because you really work up an appetite. So be prepared to spend $40 for food and drinks, or bring snacks along. And definitely bring a LOT of water. He told us where to stop to get water, but we passed it and didn't know it so we just had one bottle until we got to the winery and we really could have used more. The app was glitchy at times too, and we took a wrong turn once, down a steep hill, and then had to get back up which was challenging because you're not starting from a flat point. Anyway, all of the reviews here are so glowing, I think it's important to hear from someone who didn't have an easy time of it. I will definitely remember it, though!