Sailing Portland, Maine

Private Sailing Charters 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 39-foot cruising sailboat 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!

Testimonials

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. 

T-Shirts & Hats

Protect Casco Bay Organic T-Shirt
Protect Casco Bay Organic T-Shirt
$28.00
Save the North Atlantic Right Whale Organic T-Shirt
Save the North Atlantic Right Whale Organic T-Shirt
$28.00
Seakindly Charters Cotton Cap
Seakindly Charters Cotton Cap
$25.00
Seakindly Embroidered Polo Shirt
Seakindly Embroidered Polo Shirt
$21.50
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Boat Address

South Port Marine

14 Ocean Street

South Portland, ME 04104

Phone (207) 233-7968

Get directions