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Welcome to Calendar Islands Sailing Co. We offer custom sailing charters in Portland, Maine on the beautiful Casco Bay. Sailing out of picturesque South Portland, Maine, we allow 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., however, is that we will gladly pick up guests in Portland, on the Portland waterfront or any of 6 of the primary islands in Casco Bay, including Peaks, Great Diamond, Chebeague, Little Diamond, Long, and Cliff island.  We’re 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.


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  • Sunday24 hours open
  • Monday24 hours open
  • Tuesday24 hours open
  • Wednesday24 hours open
  • Thursday24 hours open
  • Friday24 hours open
  • Saturday24 hours open