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VOLUNTEER: After School Sailing Instructor
VOLUNTEER: After School Sailing Instructor
June 1, 2026 @ 4:00 pm - 7:00 pm
See Sign-up genius for registration and details. For questions email Jen jen@courageoussailing.org
Looking for qualified skippers to help teach kids (ages 9-14) about sailing after school. See Sign-Up Genius for a more detailed explaition.
See more details
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VOLUNTEER: Racing Skipper for Corporate Challenge
VOLUNTEER: Racing Skipper for Corporate Challenge
June 1, 2026 @ 5:15 pm - 8:00 pm
We are seeking experienced race skippers (with a laid back attitude) to join us on Mondays in join. Click here to register. Reach out to caitlyn@courageoussailing.org with any questions.
Corporate Challenge is looking for solid, patient racers to take groups of 2-3 racing. These are (mostly) fun regattas with employees from different corporations. 20 boats per night, 3-5 races, and a catered meal. Skippers are expected to rig and derig their boats. See SignUp Genius for more details.
See more details
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J80 Engine/Docking Clinic
J80 Engine/Docking Clinic
June 1, 2026 @ 5:30 pm - 7:30 pm
More details
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2
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R19 Workshop: Upwind Sailing
R19 Workshop: Upwind Sailing
June 2, 2026 @ 5:30 pm - 7:30 pm
More details
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Tuesday Night Racing
Tuesday Night Racing
June 2, 2026 @ 6:00 pm - 8:00 pm
More details
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3
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VOLUNTEER: After School Sailing Instructor
VOLUNTEER: After School Sailing Instructor
June 3, 2026 @ 4:00 pm - 7:00 pm
See Sign-up genius for registration and details. For questions email Jen jen@courageoussailing.org
Looking for qualified skippers to help teach kids (ages 9-14) about sailing after school. See Sign-Up Genius for a more detailed explaition.
See more details
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CYC Series - J80 Racing
CYC Series - J80 Racing
June 3, 2026 @ 5:30 pm - 8:30 pm
More details
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R19 Workshop: Reefing and Heaving-to
R19 Workshop: Reefing and Heaving-to
June 3, 2026 @ 5:30 pm - 7:30 pm
More details
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4
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VOLUNTEER: After School Sailing Instructor
VOLUNTEER: After School Sailing Instructor
June 4, 2026 @ 4:00 pm - 7:00 pm
See Sign-up genius for registration and details. For questions email Jen jen@courageoussailing.org
Looking for qualified skippers to help teach kids (ages 9-14) about sailing after school. See Sign-Up Genius for a more detailed explaition.
See more details
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J80 Engine/Docking Clinic
J80 Engine/Docking Clinic
June 4, 2026 @ 5:30 pm - 7:30 pm
More details
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Laser Racing
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Thursday Night Racing
Thursday Night Racing
June 4, 2026 @ 6:00 pm - 8:00 pm
More details
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5
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VOLUNTEER: STEM Activity assistant- School Field Trip
VOLUNTEER: STEM Activity assistant- School Field Trip
June 5, 2026 @ 9:30 am - 1:00 pm
For more information or to register click here. For questions about the event please reach out to Jen jen@courageoussailing.org *Short interview required, no sailing skills necessary
Students ages 9-11 will be shown interactive STEM activities. See SignUp Genius for more details.
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VOLUNTEER: Sailing Instructor- School Field Trip
VOLUNTEER: Sailing Instructor- School Field Trip
June 5, 2026 @ 9:30 am - 1:00 pm
See Sign-up genius for registration and details. For questions email Jen jen@courageoussailing.org
Looking for qualified skippers to help teach kids (ages 9-14) about sailing after school. See Sign-Up Genius for a more detailed explaition.
See more details
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Meet the J80
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6
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Brad Intermediate Racing Clinic
Brad Intermediate Racing Clinic
June 6, 2026 @ 1:00 pm - 4:00 pm
More details
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8
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VOLUNTEER: Racing Skipper for Corporate Challenge
VOLUNTEER: Racing Skipper for Corporate Challenge
June 8, 2026 @ 5:15 pm - 8:00 pm
We are seeking experienced race skippers (with a laid back attitude) to join us on Mondays in join. Click here to register. Reach out to caitlyn@courageoussailing.org with any questions.
Corporate Challenge is looking for solid, patient racers to take groups of 2-3 racing. These are (mostly) fun regattas with employees from different corporations. 20 boats per night, 3-5 races, and a catered meal. Skippers are expected to rig and derig their boats. See SignUp Genius for more details.
See more details
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9
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J80 Engine/Docking Clinic
J80 Engine/Docking Clinic
June 9, 2026 @ 5:30 pm - 7:30 pm
More details
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R19 Workshop: Anchoring
R19 Workshop: Anchoring
June 9, 2026 @ 5:30 pm - 7:30 pm
More details
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Tuesday Night Racing
Tuesday Night Racing
June 9, 2026 @ 6:00 pm - 8:00 pm
More details
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10
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CYC Series - J80 Racing
CYC Series - J80 Racing
June 10, 2026 @ 5:30 pm - 8:30 pm
More details
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R19 Workshop: Single-Handed Sailing
R19 Workshop: Single-Handed Sailing
June 10, 2026 @ 5:30 pm - 7:30 pm
More details
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11
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Green Flag Workshop On the Water
Green Flag Workshop On the Water
June 11, 2026 @ 5:30 pm - 8:00 pm
More details
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J80 Engine/Docking Workshop
J80 Engine/Docking Workshop
June 11, 2026 @ 5:30 pm - 7:30 pm
More details
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Laser Racing
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Thursday Night Racing
Thursday Night Racing
June 11, 2026 @ 6:00 pm - 8:00 pm
More details
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12
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J80 Group Practice
J80 Group Practice
June 12, 2026 @ 5:30 pm - 7:30 pm
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13
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Brad Intermediate Racing Clinic
Brad Intermediate Racing Clinic
June 13, 2026 @ 1:00 pm - 4:00 pm
More details
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14
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Cruiser Orientation #2
Cruiser Orientation #2
June 14, 2026 @ 1:30 pm - 3:30 pm
More details
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15
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VOLUNTEER: Racing Skipper for Corporate Challenge
VOLUNTEER: Racing Skipper for Corporate Challenge
June 15, 2026 @ 5:15 pm - 8:00 pm
We are seeking experienced race skippers (with a laid back attitude) to join us on Mondays in join. Click here to register. Reach out to caitlyn@courageoussailing.org with any questions.
Corporate Challenge is looking for solid, patient racers to take groups of 2-3 racing. These are (mostly) fun regattas with employees from different corporations. 20 boats per night, 3-5 races, and a catered meal. Skippers are expected to rig and derig their boats. See SignUp Genius for more details.
See more details
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J80 Engine/Docking Workshop
J80 Engine/Docking Workshop
June 15, 2026 @ 5:30 pm - 7:30 pm
More details
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17
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Courageous Cup - Corporate Sail - Hosta AI
Courageous Cup - Corporate Sail - Hosta AI
June 17, 2026 @ 4:30 pm - 6:30 pm
More details
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CYC Series - J80 Racing
CYC Series - J80 Racing
June 17, 2026 @ 5:30 pm - 8:30 pm
More details
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R19 Workshop: Docking
R19 Workshop: Docking
June 17, 2026 @ 5:30 pm - 7:30 pm
More details
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18
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Laser Racing
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Thursday Night Racing
Thursday Night Racing
June 18, 2026 @ 6:00 pm - 8:00 pm
More details
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19
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Fun Friday
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J80 Engine/Docking Workshop
J80 Engine/Docking Workshop
June 19, 2026 @ 5:30 pm - 7:30 pm
More details
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Spin Club
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20
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VOLUNTEER: Skippers for Adventure Sail
VOLUNTEER: Skippers for Adventure Sail
June 20, 2026 @ 9:30 am - 12:30 pm
Female skippers only. Its possible we may not end up needing volunteers for this event. Reach out to jen@courageoussailing.org
"Qualified skipper" requirements: Comfort working with kids / newbie sailors and confidence skippering and docking a small keelboat (tiller, no engine) in gusts up to 25 knots (Courageous Yellow Flag rating or higher). Sailing orientation / check-out required for skippers/instructors who have not volunteered with Courageous before.
Big Sister AdventureSail: 20 Big/Little Sister pairs come for a Saturday morning sail (10 Rhodes 19s, each with 2 pairs and a skipper). Most of the skippers are volunteers from the National Women's Sailing Association, who organize the event, but sometimes they need our help finding (female-identifying only!) skippers. Typically, both the Big and Little sisters are brand new to sailing. The event includes lunch (usually a cookout), and potentially knot tying etc. activities afterwards; both are optional for volunteers.
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21
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22
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VOLUNTEER: Racing Skipper for Corporate Challenge
VOLUNTEER: Racing Skipper for Corporate Challenge
June 22, 2026 @ 5:15 pm - 8:00 pm
We are seeking experienced race skippers (with a laid back attitude) to join us on Mondays in join. Click here to register. Reach out to caitlyn@courageoussailing.org with any questions.
Corporate Challenge is looking for solid, patient racers to take groups of 2-3 racing. These are (mostly) fun regattas with employees from different corporations. 20 boats per night, 3-5 races, and a catered meal. Skippers are expected to rig and derig their boats. See SignUp Genius for more details.
See more details
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23
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R19 Workshop: Downwind Sailing
R19 Workshop: Downwind Sailing
June 23, 2026 @ 5:30 pm - 7:30 pm
More details
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Tuesday Night Racing
Tuesday Night Racing
June 23, 2026 @ 6:00 pm - 8:00 pm
More details
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24
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CYC Series - J80 Racing
CYC Series - J80 Racing
June 24, 2026 @ 5:30 pm - 8:30 pm
More details
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R19 Workshop: COB
R19 Workshop: COB
June 24, 2026 @ 5:30 pm - 7:30 pm
More details
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25
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Laser Racing
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Thursday Night Racing
Thursday Night Racing
June 25, 2026 @ 6:00 pm - 8:00 pm
More details
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27
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VOLUNTEER: Dock/Land-side assistant for Charlestown Adaptive Day
VOLUNTEER: Dock/Land-side assistant for Charlestown Adaptive Day
June 27, 2026 @ 9:45 am - 4:15 pm
More information and registration click here For questions reach out to jen@courageoussailing.org
No sailing skills necessary.
Charlestown Adaptive Sailing Day: An opportunity for anyone with any kind of disability (and their family and friends) to go out for a free one-hour sail. Although a few participants are interested in learning more about sailing (or are already experienced sailors), most individuals and families are just excited to go on a chill sailboat ride. Volunteer skippers must have rock solid singlehanding and docking skills, a sense of humor and flexibility, and a willingness to talk to the people you're sailing with and see what works for them.) We're also looking for land-based help on the dock, with registration, and with meeting/greeting/helping folks get into life jackets.
See more details
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VOLUNTEER: Skipper for Charlestown Adaptive Day
VOLUNTEER: Skipper for Charlestown Adaptive Day
June 27, 2026 @ 9:45 am - 4:15 pm
More information and registration click here For questions please reach out to jen@courageoussailing.org
Qualified skippers only: Comfort working with kids / newbie sailors and confidence skippering and docking a small keelboat (tiller, no engine) in gusts up to 25 knots (Courageous Yellow Flag rating or higher). Sailing orientation / check-out required for skippers/instructors who have not volunteered with Courageous before.
Charlestown Adaptive Sailing Day: An opportunity for anyone with any kind of disability (and their family and friends) to go out for a free one-hour sail. Although a few participants are interested in learning more about sailing (or are already experienced sailors), most individuals and families are just excited to go on a chill sailboat ride. Volunteer skippers must have rock solid singlehanding and docking skills, a sense of humor and flexibility, and a willingness to talk to the people you're sailing with and see what works for them.) We're also looking for land-based help on the dock, with registration, and with meeting/greeting/helping folks get into life jackets.
See more details
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Brad Intermediate Racing Clinic
Brad Intermediate Racing Clinic
June 27, 2026 @ 1:00 pm - 4:00 pm
More details
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28
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VOLUNTEER: Dock/Land-side assistant for Charlestown Adaptive Day (RAIN DATE)
VOLUNTEER: Dock/Land-side assistant for Charlestown Adaptive Day (RAIN DATE)
June 28, 2026 @ 9:45 am - 4:15 pm
More information and registration click here For questions reach out to jen@courageoussailing.org
No sailing skills necessary. Looking for help facilitate the day with registration and life jackets. See SignUp Genius for more details.
See more details
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VOLUNTEER: Skipper for Charlestown Adaptive Day (RAIN DATE)
VOLUNTEER: Skipper for Charlestown Adaptive Day (RAIN DATE)
June 28, 2026 @ 9:45 am - 4:15 pm
More information and registration https://www.signupgenius.com/go/5080949A8A928A5FA7-63311358-aprilmayjune#/
Looking for qualified skippers (comfortable skippering small keelboats singlehandedly) to help take people with disabilities (and their families) sailing. Also looking for land based help on the dock. See SignUp Genius for more details.
See more details
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VOLUNTEER: Racing Skipper for Corporate Challenge
VOLUNTEER: Racing Skipper for Corporate Challenge
June 29, 2026 @ 5:15 pm - 8:00 pm
We are seeking experienced race skippers (with a laid back attitude) to join us on Mondays in join. Click here to register. Reach out to caitlyn@courageoussailing.org with any questions.
Corporate Challenge is looking for solid, patient racers to take groups of 2-3 racing. These are (mostly) fun regattas with employees from different corporations. 20 boats per night, 3-5 races, and a catered meal. Skippers are expected to rig and derig their boats. See SignUp Genius for more details.
See more details
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30
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R19 Workshop: Single-Handed Sailing
R19 Workshop: Single-Handed Sailing
June 30, 2026 @ 5:30 pm - 7:30 pm
More details
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Tuesday Night Racing
Tuesday Night Racing
June 30, 2026 @ 6:00 pm - 8:00 pm
More details
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Moonlight Sail
Moonlight Sail
June 30, 2026 @ 7:45 pm - 10:30 pm
More details
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