no questions are strange, some of these questions are personal choices. Unless we are leaving Colorado in the winter, I do not bring long pants. If a restaurant requires long pants, we'll eat elsewhere. Flip flops or bare feet is mostly how we roll. Again in winter I will wear sneakers on the plane. The only other footwear are my Chacos which I use for hiking. My wallet and my wifes purse are hidden on the boat for the whole trip. All we carry around is cash and one credit card. I have never been asked for ID to use a credit card. Get a dry bag from any outdoor store. We have one big enough for a laptop and a few small ones for camera or cell phone.
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