Tips here are good. If you don't run aground you aren't really trying.
Silliest one of all for us was in Hadley Harbor, near Wood's Hole. We came in early to anchor for the night and chose the little part of the harbor that had no boats in it (first hint!). Depthsounder said 14' and our draft is 5'. Anchored nicely and settled down for a relaxed afternoon followed by grilling dinner. A couple of hours later I realized that we were aground. Checked the depth sounder and it still showed 12'. Turns out we were sitting on a mound of sand with long grass growing on top to hide it. Had the BBQ and reanchored after the tide came in. toughest part was all the folks coming by in little boats to ask us if we knew we were aground. Maybe it is not running aground if you are just sitting there minding your own business.
Back in the water in Grenada - with new main and #2 and cockpit canvas (Santa came early). Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.