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: Intimate, comfortable, customized sailing experience.

Calendar Islands Sailing Co.

We offer the perfect service to make any special event not only a success, but a treasured memory. Our private, fully-custom daysails and gourmet-catered multi-day charters on our two Maine-built yachts turn the pristine rocky coasts of Casco Bay and beyond into an exclusive, relaxed escape for your team, or a spectacular setting to make a lasting, singular impression on new partners. We also provide a uniquely engaging platform for team building and leadership retreats, all with laid-back style.

Meetings > Calendar Islands Sailing Co.
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

Let our service transform your event into a landmark moment for your organization. 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.