On June 24, 2007, a group of twenty-three ten- and eleven-year-olds, fresh out of the Oak Bluffs School for the summer, gathered with their families along the Black Dog Wharf in Vineyard Haven. Accompanied by six chaperones, these students were about to cast off their normal summer luxuries – television, video games, indoor plumbing, families – to set sail on the Black Dog’s tall ship Shenandoah, owned by Captain Robert Douglas and his family. For five and a half days, the students and chaperones were swept up in a way of life that included the responsibility of working aboard a 150-foot schooner. Cooperating alongside the Shenandoah’s crew, the rookie group rose early – with or without coffee – to swab the decks, perform galley duty, and haul the anchor. They sailed a little when the wind was right, and they got to jump overboard to go swimming. It was a flashback to what would have been second nature to many Island youngsters only a century before. After the trip, some students and chaperones shared their diaries with the magazine, which have been edited to include in this photo essay.

Since 1993, this trip has become a rite of passage for many fifth graders on Martha’s Vineyard. Upwards of 2,250 Islanders have been part of this fifteen-year tradition, which gives students the opportunity to acquire their sea legs at a reduced rate and with a group of youngsters they already know. Kids react to the experience of camping on a boat in different ways, but in the end, they certainly learn more about those big, impressive vessels they see year-round in the harbor. “Kids are our specialty,” says Captain Douglas, whose only regret is not starting this tradition twenty years earlier.

3:30 – all hands on deck! Sails are going up, everyone must help. Emelia loses her visor in the water and the first mate retrieves it for her. Toward Falmouth at 4:00. We got close to Woods Hole, turned around, and headed toward State Beach, where we anchored for the night. We put down the sails, then had dinner: hot dogs, salad, and potato salad. This day was so perfect and we are so very lucky to have this experience.
– From mom Sylvia Cappelli’s diary

Dear Shenny Trip 2007,

June 27, 2007 8:45 p.m.:
Howdy! Today was really fun. This morning we had deck wash, then we had yummy granola with
yogurt, and then we went swimming. Guess what?
I learned how to dive.
It hurt at first, but now
I’m a pro.

June 28, 2007:
We caught sharks and
sand sharks. They were cool. Molly caught the
biggest.
– From Alex Clark’s diary  

Two squealing cold-water pumps, 2 toilets, 40 people, $600, no shower, being awoken
at 3 a.m. by a kid falling out of a bunk, being yelled at by the first mate, not enough room to roll over in your bunk, all hands on deck at 7 a.m. to clean. A week spent with your kid
on the Shenandoah…priceless.
– From photographer and mom Alison Shaw’s diary

Dear Shenny Trip ’07, Today we “swabbed” the deck at 7 a.m. sharp. Then we had
breakfast. It was good! We had pancakes and bacon. Then we hung out for a while and
went swimming. After that we put up the sails and cranked the heavy anchor up with
this crank. We went to State Beach and put the anchor down. We had dinner, which was spaghetti, and now it’s time for bed. Love, Isabelle