Custom Sailing Charters
Portland, Maine
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We pride ourselves on flexibility. Our custom sailing charters are not restricted to a certain schedule. We create an experience just for you. Whether you are interested in a private 2-hour coastal sight seeing sail, an all day island hopping cruise, or an overnight adventure, or one of our four times Daily Public sailing trips the choice is yours.

Casco Bay plays host to some of the most beautiful and diverse scenery on the Maine coast. From the rugged rocky cliffs and bays of the many islands to the gently wooded shorelines of the mainland, the views will charm and captivate you. Casco Bay is home to some of the most beautiful lighthouses in the state. There are more than 136 islands, providing no shortage of sights to see and places to explore in this ocean playground aboard our custom sailing charters.


Let us be the venue for your most memorable event.  We will create the perfect atmosphere for your marriage proposal, elopement, photo shoot, reunion, bachelor or bachelorette party, the highlight of your family vacation, any special event you envision.  What more elegant way for a bride and her attendants to arrive at her island wedding, or for the the newly married couple to depart? 

For special events please contact us for a quote.

We dodged thunderstorms and we're rewarded with a picture perfect maine sunset!  With _reneelaplante


Welcome to Calendar Islands Sailing Co. We offer custom sailing charters in Portland, Maine on 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 or 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 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.



We are docked at the brand new Fore points marina in beautiful, downtown Portland, Maine. found at 58 Fore Street we are just a short walk or ride from the majority of the hotels in Portland. 

We can be reached by Phone at: 207-318-3025

we also can be reached via e-mail at: info@sailcascobay. 

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