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Calendar Islands Sailing Co.

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Welcome to 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.

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

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.

Calendar Islands Sailing Co. EVENTS

Sails and Ales

Jul 11–Sep 26
Fore Points Marina, Portland
Hop on board a beautiful Maine-made sailing yacht to drink local beer while cruising Casco Bay.

Sails And Spirits

Jul 12–Oct 11
Portland, Maine
Join us for an evening of sailing and the finest craft spirits in Maine.
Send Inquiry:
58 Fore St
Fore Points Marina
Portland, Maine, 04101
(207) 318.3025
ABOUT US
  • 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.
Welcome to 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.

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

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.


Calendar Islands Sailing Co. EVENTS

Sails and Ales

Jul 11–Sep 26
Fore Points Marina, Portland
Hop on board a beautiful Maine-made sailing yacht to drink local beer while cruising Casco Bay.

Sails And Spirits

Jul 12–Oct 11
Portland, Maine
Join us for an evening of sailing and the finest craft spirits in Maine.
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207-772-5800 | info@visitportland.com