My dad and I took paddleboarding tour with Lazy Dog and had a great time! We ended up being the only ones signed up, so we got basically a private tour with our knowledgeable guide, Heather. After a short lesson, we were both up on our boards and out on the water, learning about the area and the wildlife that lives there. I was a little nervous about it being too difficult for us, but we got the hang of it quickly and Dad only fell in the water once. :)
If you are looking for something fun to do during your time in Key West, try paddleboarding with Lazy Dog. They were friendly and it was very easy to find!