1) Don't shop for the perfect present when you have a skill like art, cooking, or theater. Entertain your guest with a little song & dance, maybe whip up a DIY project or even get your Martha Stewart on and make specialty holiday baked goods.
2) Wear basic leggings (elastic for the sake of seconds,.. and thirds) with an oversized sweater, festive socks paired with boots and the most neck engulfing scarf you own! Remember you don't actually have to dress up, just wear one thousand layers, so as you make your stops you can be comfy and prepared for anything.
3) Instead of making small talk of 'what you're up to these days', initiate a snowball fight. I'm just kidding! I'm sure Grandma would not like that in her house, just bring along a fun bored or card game that everyone can engage in. Alternatively, ask a random question such as, "What inspires you these days?'
4) The best part of the holidays is that weather can interfere, so if you are worried about traveling stay home! I have found that the best Christmas I ever experienced was because the weather was so bad we just stayed home in our PJ's, mom made so much food, we drank mimosas, watched football and opened presents.