After leaving the Basin, we threaded through rocky coastline to our next stop – Snow Island in Quahog Bay, where we tucked in behind the island for the night and enjoyed a vibrant sunset at anchor. The next day, we moved over to Safe Harbor Great Island, where our friend Blaine would be joining us for the next few days. Blaine sailed back from the Bahamas with us our first season cruising, and we were excited for the chance to take him out on Windara.

We took him out for a dinghy mission, where we spotted a bald eagle and explored Little Snow Island, one of the Maine Island Trail Association’s islands. We all spent Friday working, and Saturday morning we made our final hop to get into Casco Bay. The forecast was calling for high winds and big seas, and leaving Quahog Bay was a tackfest through a relatively narrow channel with rocky ledges on both sides. But Windara felt good, and with three people it was much easier to handle all the tacking. Once on open water, we were seeing 6-8′ seas but with a longer period, so they were fine and the sail down to Casco Bay was actually quite nice.








Our original plan was to get dock space in Freeport so Blaine could get back to his car, but the dock was full so we spent the night anchored off Chebeague Island, well protected from the wind (but less so from ferry wake). The next morning we moved over to anchor off of Long Island where Blaine caught a ferry, and we headed ashore to explore.
The more we explore, the more the Maine coast feels like home. Each new place has its own character, yet each evokes its own little snapshot memory of when I was a kid on Cape. Maine summers feel like one big summer vacation, even though we’re working.




Everyone on the island is so friendly – drivers wave, people pause on their doorstep or on their golf cart for a brief conversation even though we’re strangers. Island life calls to me, be it in The Bahamas or up along the rugged coast of Maine. It’s my speed, it’s my tribe.

We’re so excited to be exploring Casco Bay. Last year, we were in a big rush to get up to Belfast so we could get our refit quote, so we really only got to see Portland, and then not all that much. The best part of Maine cruising is that there’s always a new, interesting anchorage nearby, and we can’t wait to discover what awaits us here.
















