Personally, I wouldn't go out when your baby needs to nap, unless you absolutely can't avoid it. The most restful sleep happens in a quiet setting (at home in the crib). It is hard to nap on the go (whether in the stroller or in the car). I would certainly have a hard time napping, and if I did nap, I know it would not be uninterrupted and restful. I plan my outings for when my baby is awake, and we head home when it is nap time. Eventually, your baby's wake times increase, and baby will nap fewer times a day, meaning you will have more freedom as baby gets older. If you need to go out during nap time, plan on bringing something to keep your baby entertained, if you know that he/she is not good at napping while you are out.