I did this often. Alone, with B, with friends. I saw sharks. I watched someone fall out of his kayak. I spent the first day of my 30s kayaking around the island (followed by a lobster dinner prepared by B, a pedicure, and drinks with friends).
Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover. -Mark Twain