Donate to watch your friends… and maybe your enemies…
WALK THE PLANK
JUNE 14TH
Anyone can sign up. Only the top 15 fundraisers earn the jump
Wait, What?
Yes, you heard right - Walk the Plank on June 14th!
Each year brave fundraisers compete for the honor of walking the plank off the 137’ schooner Denis Sullivan into Boston Harbor.
Anyone can sign up. Only the top 15 fundraisers earn the jump.
All funds raised support our education programs for area youth aboard Denis Sullivan. Since 2002, more than 25,000 students have sailed with us, gaining hands-on experience in teamwork, leadership, and life at sea.
Help us continue bringing life-changing education to local students. Think you can make the top 15?
JOIN THE CREW
Top fundraiser has their name etched on the Walk the Plank Plaque and win a free private charter
Top three fundraisers receive Walk the Plank trophies
All jumpers receive a special Walk the Plank gift package
2026 JUMPERS
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Ari Skidmore-Hess
Donate to Ari’s campaign today!
Donations raised: $1,385.00 -
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Fred Eustis
Donate to Fred’s campaign today!
Donations raised: $1,000.00 -
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Cassie Scarano
Donate to Cassie’s campaign today!
Donations raised: $300.00 -
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Captain Flansburg
A mutiny is in order… Donate to Cap’s campaign today!
Donations raised: $50.00 -
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Andrew Sanchez
Donate to Andrew’s campaign today!
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This could be you!
Get a head start on your campaign today!
Why We Walk the Plank
Every dollar raised helps bring area youth aboard the schooner Denis Sullivan for hands-on learning at sea.
Students learn science, teamwork, and leadership while sailing Boston Harbor and beyond.
Since 2002, more than 25,000 students have participated in World Ocean School programs.
Event Details
Watch fundraisers take the plunge off the schooner Denis Sullivan into Boston Harbor while guests enjoy music, drinks, and waterfront views from the deck or along the Harborwalk.
How to get tickets
Donate $100 or more to a jumper’s campaign to receive one event ticket.
Each additional $100 donation earns one additional ticket (up to 8 total).
After donating, you will receive an email with a link to register your ticket(s).
Registration is required. Space aboard the ship is limited, and we cannot guarantee entry without advance registration.
Date:
Sunday, June 14th
Time:
4:00-6:00 pm EDT
Location:
Moakley Courthouse Dock 19 Northern Avenue, Boston, MA 02210
What to Wear
Bring your costume, your bathing suit, your business suit, or any outfit you can dream up
Past Costumes
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The Duke
Even royalty must answer to the plank.
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The Cat in the Hat
The Cat in the Hat took a splash like that
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The Cactus
Desperate for any type of water.
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The Marlin
Catch and release.
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![Bagel with Cream Cheese]()
The Bagel with Cream Cheese
Bagel. Schmear. Splash.
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Superman
Up, up… and straight into the harbor.
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Scuba Steve
The only jumper who came prepared.
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The Watermelon
Salt-Watermelon.
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Chewbacca
A long time ago… in a harbor not far away…
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The Colonial
Throwing all the tea over was not enough.
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The 80's Fitness Trainer
Splashercise
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The Kraken
Davy Jones was not pleased with its efforts.
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The Shark
Our contribution to Shark Week.
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The Red Buoy
Boston Harbor’s most committed buoy.
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Elvis
The King of making a splash
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The Pirate
It wouldn’t be Walk the Plank without one.
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The Clown
Walking the plank is no joke!
Become a Sponsor
Partner with Walk the Plank and connect your brand to one of Boston’s most unique waterfront events.
Ready to Take the Plunge?
