Charley's is what it is—a bar. I didn't know about the Willie Nelson connection until after stumbling on Charley's for the first time. Could not care less either way. It had two things that we wanted: beer & bar food. And it delivered. Excellent beer selection. Bar food is exactly what you want it to be. Like finding that perfect pub with perfectly ordinary but warm pub food on a miserably rainy day in Scotland. Only here, the day is likely to be gloriously beautiful.
I know others here have complained about the staff, but OMG, I love them. I think they are friendly and accommodating and can be very talkative. This is one part of local Hawaii that is as far away from the Grand Wailea as possible, and you should not miss it. In this bar, as a tourist, you are an outsider. They will make you feel as welcome as you want them to, as welcome as you want to be, if what you want is to appreciate being in a cool, laid-back, comfortable-as-a-worn-out-pair-of-jeans place in one of the most beautiful places on the planet. Bring your traveler persona, and leave your tourist bad self outside.
Been here as a couple, solo, and family, all good. Been here crowded in the evening, and quiet in a lazy afternoon. Both are nice, though I prefer the latter. With great music playing in the background, the locals relaxing, it is a different kind of place to relax and enjoy being human.
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