Calendar Islands Sailing Co: Intimate, comfortable, customized sailing experience.
Calendar Islands Sailing Co: Intimate, comfortable, customized sailing experience.
Calendar Islands Sailing Co: Intimate, comfortable, customized sailing experience.
Calendar Islands Sailing Co: Intimate, comfortable, customized sailing experience.
Calendar Islands Sailing Co: Intimate, comfortable, customized sailing experience.

Calendar Islands Sailing Co.

As Casco Bay’s only provider of truly custom sailing charters, as well as the bet small group public sailing trips in Portland. we offer a uniquely individualized gateway to Southern Maine’s peerless coastal sailing destinations. Calendar Islands Sailing Co. grew from the simple idea that a more personal setting and a more relaxed, less crowded boat offers the best possible on the water experience.

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Contact

58 Fore Street Marina
Portland, ME 04101

P. (207) 318-3025

About Us

We offer four, regularly scheduled 2-hour long public trips each day at:
10:30 am
1:00 pm
3:30 pm
6:00 pm

Should you choose to private charter, we deliver an exclusive alternative to other boating companies; an intimate, comfortable, tailored sailing experience, second to none in satisfying the needs and desires of our guests. Our beautiful Maine-built yacht an Alden Boothbay Challenger – offer day sails within Casco Bay, and multi-day, gourmet-catered charters all along the Maine coast. And, though we sail out of South Portland, we are happy to pick up and drop off guests from the Portland waterfront, and any of the six of the primary islands in Casco Bay – Peaks, Great Diamond, Little Diamond, Long, Chebeague, and Cliff.

Whatever your vision for how you will explore and enjoy the Maine coast, let us help you make it entirely your own, and take you there in effortless elegance.