It is much more convenient to have friends with sailboats than to go through the hassle of owning one*. Sailing is always so spontaneous. Your friend calls and asks you if you want to go out on her dads new, upgraded boat. You either drop all your plans for the day or don’t.** There’s no wiggle room. You grab some snacks and your fleece pullover and meet them at the yacht club in Bayside.
We had no plans for where we would go, but we ended up sailing over to Castine. I had never been to Castine by land let alone by sea. There is a true sense of adventure when you can sail to new places, decide on a whim to stop, and pop around on land for a little bit. I’m not sure there are many ways to get that same sense of adventure anymore. We walked around the immediate neighborhood, had a root beer float, and then headed back across the water. I even got to drive the boat a little bit (it’s not so hard but it takes some getting used to).
I was told that one of the reasons Penobscot Bay is one of the best places to sail in the country is because there are so many islands (many uninhabited, like my running island) where people can stop and explore. Other reasons cited were the beauty and that you can get the beauty and the sense of adventure without the crowds. Also the winds are pretty good.
Some of the pictures above show Cadillac Mountain peaking out behind Islesboro, A shot of the harbor from the streets of Castine, the boat we sailed on, and the ledges at Turtle Head (which is a preserved nature area on Islesboro).
*coming from someone who has never and will never own a sailboat. **you do.