Anna Sprague, a sail trainee aboard the Picton Castle, lowers the anchor light at sunrise off the coast of Gloucester, Mass.

Capt. Sam Sikkema oversees the loosening of the sails as the Picton Castle, bound for Portland, departs Gloucester, Mass., on Friday. Gregory Rec/Staff Photographer

As rain starts to fall, Naomi Radtke Rowe loosens a line on the barque Picton Castle while it was moored off Gloucester, Mass.

Xander Davenport of Lyman, right, holds fast to a jib line on Monomoy while sailing off the coast of Gloucester, Mass. The small boat is used for sail training.

Mazie Linsmith, a sophomore at Casco Bay High School, catches a line thrown by Garrett Marques from the Monomoy, a small boat the crew of the Picton Castle use for sail training. Linsmith and other students sailed on the Picton Castle from Greenport, New York, to Portland.

Dan Morse of Yarmouth attaches a sail aboard Picton Castle.

Morse coils a line aboard the barque Picton Castle.

Julien Peck, a sophomore at Casco Bay High School, coils a line aboard Picton Castle.

Morse rinses lines and straps in a bucket of fresh water aboard the Picton Castle. Morse graduated from Yarmouth High School last year.

Light from nearby Boston colors the night sky as Davenport, left, talks with Steve Hopkins, an experienced sailor from New York, while the two sit aboard the Picton Castle.