DS never, ever slept when we were out and about, except for in the car. I avoided trips around nap times, or he'd have his nap in the car on the way there and another in the car on the way home. I'd often have to keep driving, so got to do a bit of sightseeing (made the odd trip through the drive through too!). Sometimes I could park somewhere for a bit while he slept, or I'd sit in the carport with him if we were home.