Private Sailing Tours in Portland, Maine

Private Sailing Tours on Casco Bay

Book online  or call Capt. Brock at (207) 233-7968 to make a reservation

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See Casco Bay by Sailboat!

Seakindly Charters offers custom, private, captained sailing charters out of Portland, Maine, for groups up to six people aboard our 35-foot cruising sloop named Juliet. Join us for a two-to-six hour sailing trip, and we'll show you the lighthouses, islands, and natural beauty of Casco Bay. Have some sailing experience? Feel free to take the wheel and hoist sails, or just relax and let Captain Brock take care of everything.

Welcome aboard!


My family has sailed with Brock numerous times and always had a great time. Juliet is a great boat!

G. Lull

Great boat, great crew, and some of the best cruising ground available anywhere. Would highly recommend hiring Brock.

R. Williams

Sunset sails are our specialty

Join us for a two or three-hour evening sail around Portland Harbor. It's magical. 

Blog posts



Seakindly is now taking reservations for the 2019 spring and summer sailing season in Portland, Maine.
Getting Ready for 2019!

Getting Ready for 2019!

Seakindly's 2019 charter sailing season in Portland, Maine, will run from May 24 through October 13. We will again be based out of South Port Marin...
Promo code CYBER gets 20% off Seakindly Schwag through Nov. 30

Promo code CYBER gets 20% off Seakindly Schwag through Nov. 30

Stay tuned for sailing charter reservation info for the 2019 season. In the meantime, enjoy 20% off on all t-shirts and hats here on seakindlychart...

Boat Address

South Port Marine

14 Ocean Street

South Portland, ME 04104

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