We went to the beach recently and I brought my paints along. I took some photos so I could show you about my experience painting on the go, or plein air as it's officially called.
When I first tried painting outside I ran quickly into all the reasons people paint indoors so often: it's tricky to find a place to sit, and then to figure out how to hold your paper, paints, water and the rest without everything spilling. And then there's the variables: rain and wind, light that glares or moves or disappears, etc. It seems like more things would make it easier (bring a chair! an easel! a tripod!) but then you have to pack and carry those things. I tend to think of myself as something of an "indoor person" to begin with, so to be totally honest, I don't paint outside too often. And when I do, it's usually quite near my house or car, where I have brought along tons of stuff. There are many people who are much, much, much, much, much, much better at painting outdoors than I am.
That said, even as a temperature sensitive, wet ground averse person, even without the ideal set up, there are things I love about making marks outside, and I have found some strategies that work for me that I'd like to share in case these spark some ideas for you.