All three of mine have been going up to my parents' lake house since they were puppies. They are off-leash the entire time we are up there, unless Jasmine is feeling stubborn, then she gets a leash put on her during our walks. That normally will only happen once because she hates having to be on leash and starts behaving again.
In the city, Jasper is the only one I would allow off-leash. He goes to and from my car without a leash. But even as much as I trust him, I wouldn't do it near a busy road. He and Danny have very, very good recall. Though if Danny gets distracted, I just tell him to sit and he does, wherever he is. It's pretty funny!