If he will nap in the car I would go for a drive in the afternoon until he fell asleep. Once he falls asleep go home & sleep in the car with him. Hopefully, he will get an hour or two nap & you will too. That may be enough to break the cycle. You could also do this at night time before bed.
Good luck.
After reading responses I wanted to add that the cuddly/quiet thing doesn't work for all kids. My three year old & I often run races before bed time. We sprint around the living room (my 2 year old often watches tv while we do this) for 20 minutes & then head up to bed. Sometimes we do a bath, sometimes not. Sometimes we read a story, sometimes not; depending on how close to bed time it is. I always sing a song before bed. My youngest likes me to hold him while I sing. He needs a few minutes of extra cuddling before sleep. We also have 2 night lights & each boy has his own "night buddy" an in bed soft glow night light. I think its really called a tyke light. They sleep with a ton of stuffed animals, pillows & blankets. And recently started to sleep with each other. Their bed is very crowded & cuddly & it makes them happy. So, try lots of different stuff. You don't know what will work.
Also, my older son went through a similar phase when he was 2. Finally, one night I told him that no matter how much he cried I was not going to pick him up or bring him to my room. I would come & check on him, but then I would leave immediately. I told him that all his wake ups were making me tired & grumpy & I didn't want to be a mean mommy. So, he needed to sleep the whole night. That night when daddy came home from work & went in to kiss him good night my son told him that mommy is tired & needs to sleep, so I'm going to sleep all night to help her & make her happy. He did! The next night i reminded him of the same thing & he slept through the night again. The third night he did it with no reminders & it hasn't been a problem since.