Kayaking
Kayaks weren't the first boat that I ventured out in on my own, but they were pretty soon afterwards. I think the first might have been a rowboat tied to the dock. However kayaking has become one of my favorite activities.
Specifically whitewater kayaking, but I do also have an appreciation for sea kayaking also. As of drafting this page, I have paddled a grand total of one class V, which was a mistake, but I am working towards paddling class V more often. A mistake, yet a story that I should try to tell at some point.
Growing up on the ocean every summer, and at Plum Island often during the weekends while my dad was windsurfing I love to go out in other types of boats too, just like most of my family. If you just count my relations that live in Maine we have a small flotilla at our disposal. When I was younger I would head out sailing around the coast with my grandparents, or we would head up the back way to Bath to terrorize one set of cousins before heading outside to have a rowdy gathering with the others.