Blog posts tagged in Sailing
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 By Ali Maas

Nestled between three highways and an ocean of urban sprawl lays Jamaica

Pond. My entire life I have driven past Jamaica Pond and for years, I sat in my car,

saw a flash of white sails, and wished to be on the water. All I knew of the pond

was tiny moments speckling my life. This year many young Bostonians just

entering Swim Sail Science, Summer Learning Project, and Summer Youth

Program, and I discovered the vastness of Jamaica Pond. Led by veteran pond

travelers of summers past, we discovered the draw of Turtle Island and its

incredible ability to act as the perfect mark in any wind condition. We discovered

where the wind dies, and where the wind strengthens. Our ability as sailors

intensified as winds shifted ninety degrees and when winds died, we mastered

pointed drifting. The pond is never still. It is constantly in flux and forever

testing ones skill as a sailor to adapt. On any given day, one can see a little

turtlehead peeping from the surface.


The pond alone could make any summer job great but what makes this the

greatest summer job is truly the students. The only sad day I have had this

summer was this past Friday when I had to say goodbye to the students I have

spent the last four weeks teaching. Seeing two Swim Sail Science students who

came as best friends leave with fifteen new friends. Remembering when one such

student led his own chalk talk and each of his classmates jumped to lead their

own. Watching three Summer Youth Program students who had never sailed

alone tack on the whistle in perfect synchronization while skippering their own

periwinkle( a small wooden sailboat). Wiping glitter off the counters from

Thursday Race medals (coined the Jamaica Pond Cup) the Summer Learning

Project students begged to race in each week. What made me smile most that

Friday was hearing one student proclaim that he wanted to sail in college one day

just like me. I told him I would tune in to ESPN to watch him in nationals.


Sometimes it can be hard to remember why we sail. When its thirty

degrees outside and I’m sitting in the eighth hour of racing, gusts of thirty

nipping at my cheeks, I can forget why it is I sail. Now, all I have to do is

remember that little kid, soaked from capsize drills, so in love with sailing that he

gave up a week of baseball camp to come back, telling me he wanted to sail just

like me. I am so lucky to have been able to teach him, to see so many students fall

in love with sailing just as I once did. Most of all, I will always have the reminder

of my younger self, looking out the car window at Jamaica Pond, wanting only to


By Kayla McLaughlin, SwimSailScience and Summer Learning Project Head Sailing Instructor


“Teachers of young children do one of the best things that there is to do in life: bring joy and beauty, mystery and mischievous delight into the hearts of little people in their years of greatest curiosity”  -Jonathan Kozol

For the past three years I have had the pleasure of working with children from the Boston Public Schools, through the SLP and SSS programs. In that time, I have seen just how fitting the above quote is. It has been inspiring to watch 3rd, 4th, and 5th graders from some of the most difficult neighborhoods of Boston, conquer their fears, discover their passions, and accomplish their goals while sailing on the harbor.

After going sailing everyday, I usually gather my students, and talk with them about how their sail went. Everyone typically shares something they learned, something they are curious about, or a fear they had while out on the water. A few weeks ago, I was talking to Tyrese and Kathia about how their mornings went. Tyrese, a student from the Sarah Greenwood School, was having difficulty overcoming his fear of windy days. When I called on Kathia, a student at the Harvard Kent School, to tell the group what she learned on the water, she explained “Today, I learned that overcoming your fears makes you stronger”. When I asked, she elaborated, stating, “We were tipping over so much today, we got water in the boat! I knew Tyrese was scared, so I held his hand. I really liked how we worked as a team to overcome our fears. I also felt really brave, because I picked up the jelly fish that was in our boat, and put it in the water”. After her beautiful explanation, I asked Tyrese and Kathia if they felt like sailors, to which they both smiled and responded, “yes!”

Every day, I watch my staff kindle “mystery and mischievous delight” into the hearts of our students, and the students have done the same for us. My instructors and I celebrate amazing victories, such as the one I described above, and I consider it an honor to use sailing as a way to build confidence, conquer fears, and establish camaraderie and a sense of community for the young people of Boston.