Welcome to Calendar Islands Sailing Co. We offer private sailing charters in Portland, Maine on beautiful Casco Bay, inviting you to design your own personalized and flexible excursion. Founded in 2015, Calendar Islands Sailing Co. is based upon the simple idea that a smaller more intimate setting creates a more enjoyable on-the-water experience.
One of the most unique features of Calendar Islands Sailing Co. is that we will gladly pick up guests on the Portland waterfront or any of the six primary islands in Casco Bay, including Peaks, Great Diamond, Chebeague, Little Diamond, Long, and Cliff islands. We are proud to offer island pick up at no additional cost to our guests.
We offer an exclusive alternative because we operate on a private-charter-only basis, providing an intimate, comfortable, customized sailing experience suited to the needs and desires of our guests, second to none.