I've never cycled naked. I suppose a WNBR would be an option, otherwise I can't think of where I could even try. Perhaps a night ride, but I'd need to fix or replace my lights for that. Daytime would be problematic for me as I usually try to avoid surprising textile types and would want to cover a reasonable distance.
I have done it for some portion of a trail, but in the evening. I usually go one way dressed, and then check how many people are on the trail. If super busy, I will not try. But I have done a good portion, far from houses, once the sun is out. It's nice. Like it. But it's risky thing to do.
My local trails are mostly linear ones along creeks with access at multiple points to other trails and road crossings. They're popular with cyclists, runners, dog walkers and regular pedestrians. It might be a while for me to find an opportunity!