• Fall is the perfect time to experience Boston Harbor, and Courageous Sailing is offering special deals for Charlestown residents. Summer vacation doesn’t need to be over.
  • Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Summer Youth Sailing Program
  • Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families


Sunday, Oct. 23nd: CLOSED FOR THE DAY, due to a gale warning and gusts up to 35 knots through this evening.
  • Work for Courageous

    Love sailing? Love teaching? Courageous is currently hiring for a variety of seasonal and summer jobs for our youth and adult programs. Spend your summer sailing with kids, teach sailing to adults on weekends, or help run one of our programs! Read More
  • Summer Youth Program Registration

    Registration is now closed. View the FAQ to learn what to do if your child was registered successfully or put on the waiting list. The FAQ also details the 2016 fees and scholarships. Read More
  • Sail Boston Harbor!

    At Courageous, we’re committed to providing some of the best and most affordable sailing opportunities on Boston Harbor for adults and families. Whether you’re a total beginner or an expert sailor, we’ve got a course or membership to fit your needs and interests. Read More


Special thanks to our Courageous Sailing foundation, corporate, and philanthropic partners.



Cummings Foundation MableLouiseRileyFoundation Anonymous

$20,000 to $100,000

John Hancock logo Distrigas-Logo peterson party center LG

$10,000 to $20,000

Harvard Pilgrim Fallon Company 11th-Hour-Racing-Logo No-Tag-Line-300x124 TK Logo cmyk hi-res-1024x347

$5,000 to $10,000

Fortress Coyne-Fund-Trust Mesirow Mellon Capital
Barefoot-Regatta-Logo alphagraphics logo Fidelity State-Street-Logo Bain Capital

$1,000 to $5,000

Marcum LLP

Commvault Systems

Joanne L. Shrontz Family Foundation


WJ Lynch Associates

State Street Foundation

HBB Foundation

Boston Boatworks

Premier Bartending & Beverage Service



Bank of America Merrill Lynch



Sperry Top-Sider

Leggat McCall

Mayflower Advisors

Boston Private


Patriot Energy

Atlas Venture

Eaton Vance

Brooklyn Boulders


Courageous Sailing is a nonprofit, 501c3 organization. Our programs rely on the generous support of a growing community of individuals, foundations and corporations that support our mission to transform the lives of Boston's kids through sailing programs that inspire learning, personal growth and leadership. Support comes in many forms, from an annual volunteer day to a donated auction item, from giving $5 at a weeknight cookout to heading up a team in our annual Corporate Challenge. Courageous truly stands out through the character and commitment of the people and organizations who help make our programs available to everyone.

Individual Support

Personal donations are a key part of our funding. Every gift helps, and every time you come to Courageous you are doing your part to support our programs. Whether you are a new or long-time member or you just came down with a friend to try racing one evening, you are helping to support Courageous kids and increase the community's access to Boston Harbor. We thank everyone who has given to support our mission. To give, click here.

The Waiver

The Courageous Sailing Agreement & General Release and Membership Terms & Conditions form, also known as the 'Waiver' is required to participate in all activites hosted by Courageous Sailing at our Charlestown Site. All participants, members, guests, etc. must sign the waiver once per season. The form is available below for electronic download. We encourage you to review it carefully so you understand your rights and responsibilities. The form is electronic, so you may complete it on your computer, phone or tablet. You may also print it out and bring it with you on your first visit of the season. Hard copies are available at the front desk should you wish to fill it out when you arrive.

Office/Business Manager

Reports To: Executive Director
FLSA Status: Non-exempt
Status: Full-time
Date of Last Revision: September 2016

Position Summary

Courageous Sailing, a 501(c)3 nonprofit engaged in sailing education for Boston youth, seeks a high energy office manager to keep the wheels turning at our boat house on Pier 4 in the Charlestown Navy Yard. Bookkeeping, HR and payroll processing, organizational management, and regular communication with staff and board members comprise the basic requirements of this position. Working alongside a committed staff, the well-organized, detail-oriented self-starter has the opportunity to transform these abilities into specific transferable job skills within a supportive, fast-paced work environment.

Reporting to the Executive Director, the Office/Business Manager takes primary responsibility for managing the non-programmatic aspects of the organization. This position is fundamental to the organization’s ability to operate smoothly and economically. The Office/Business Manager operates on a broad spectrum with major tasks including oversight of the essential business functions of the organization, including bookkeeping, human resources, technology, events and general administration. A true team player, the Office/Business Manager is involved with many aspects of the organization and works closely with the Executive Director to assist in both daily and big picture operations.

The ideal candidate will possess an excellent work ethic, organizational skills, and capacity for multitasking; experience with database, accounting and spreadsheet software; exemplary communication and writing skills; and the maturity to responsibly handle sensitive information and situations.


These include, but are not necessarily limited to, the following:

  1. Information Management
    1. Maintaining our donor and constituent database and coordinating the use of the system by program staff
    2. Administering cloud-based resources such as Google Apps, Dropbox, Smartsheet and Asana
    3. Updating office technology as needed, including both hardware and software
  2. Bookkeeping
    1. Working directly with accountant, Board Treasurer and ED to ensure appropriate financial controls and oversight
    2. Tracking, processing, and depositing all incoming and outgoing monies
    3. Assisting with cash flow tracking, financial reconciliations, and reporting
    4. Assisting with budget planning
  3. Human Resources
    1. Maintaining all payroll records and managing the timely submission of payroll reports
    2. Processing all hiring documents, including CORI and SORI requests
    3. Tracking and updating insurance plans, payments, and renewals in conjunction with our broker
    4. Managing benefits for staff members
  4. Administrative
    1. Keeping updated records of all current contracts for reference and acting as a liaison on behalf of Courageous and staff to organize contractual agreements and/or renewals
    2. Ordering office supplies and merchandise as needed
  5. Events
    1. Conducting site reviews and building relationships with event planners and caterers in the area
    2. Acting as a contact for all pier rental inquiries and helping to track and schedule all events
    3. Overseeing the logistics of fundraising events, including organizing sponsorships and auction catalogs, set-up, day-of coordination, and staff management, as well as tracking attendance, ticket sales, donations, and receipt of any auction or raffle winnings
    4. Working with City Hall to obtain all seasonal and one-day event licenses 

Qualifications / Skills

  1. Excellent organizational skills and attention to detail
  2. Excellent communication and interpersonal skills
  3. Fluency with Salesforce or similar database; Microsoft Office, especially Excel; and social media
  4. Familiarity with Quickbooks or equivalent or basic accounting practices
  5. Ease in managing multiple projects simultaneously, working independently and under a deadline, prioritizing responsibilities, taking initiative, and appropriately handling confidential information
  6. Bachelors Degree
  7. 1-3 Years office management experience preferred

About Courageous

Courageous Sailing is a non-profit sailing center dedicated to transforming the lives of underserved populations of youth through sailing.  The program has been in continuous operation since 1987 and is based in the Charlestown Navy Yard on Boston Harbor.  The youth program is supported by the operation of the adult program, grants, corporate sponsorships, individual donations and fundraising events. 

Courageous Sailing is an Equal Opportunity Employer.

Courageous Sailing does not discriminate in employment on the basis of race, color, religion, sex, sexual orientation, national origin, age, genetic, disability or veteran/Reserve/National Guard status.

Community Partners

Strengthening and extending the relationhips in our community is a foundational principal of Courageous Sailing. We establish community partnerships as a benefit to our members as well as those outside of our organization. If you are interested in becoming a community partner, please contact Dave DiLorenzo at dave@courageoussailing.org Current active members of these organizations are invited to enjoy 10% off individual and family memberships and 10% off most learn to sail courses.


BKBS CBI Piers Park


Neighborhood Partners

We are fortunate to have location in the Charlestown Navy Yard with a number of residential and commercial neighbors in the surrounding blocks. As a member of this community with a historical connection to Boston Harbor, Courageous is proud to offer easy access to sailing for our neighbors. For information about special neighborhood pricing and events or to learn how you can become a neighborhood partner, please contact Dave DiLorenzo at dave@courageoussailing.org


spaulding MGH YMCA
Unknown  CWC charlestown seal

More Articles...

  1. 25 Year Slogan
  2. Charlestown


Learning the Ropes
Youth Program
I had a great summer at Courageous Sailing and have had a number of memorable experiences with kids on the water. One that stands out most to me happened with a student in Step 2. This student was always his own person and has a very colorful disposition but, because of this, had trouble showin...
Continue Reading...
Mi Barco es Su Barco
Youth Program
The Swim Sail Science! program at Courageous this summer was very different than the summer youth programs that we have always had. Half of the students' summers were spent in math and reading classes, where they learned about different water systems and our limited supply of fresh water i...
Continue Reading...
Why We Keep Coming Back
Youth Program
During the summer of 2012, JB enrolled in the SLP program for the first time.  It also happened to be my first year of instructing, and it was safe to say that she was one of my most unique students.  If her constant curiosity for sailing or insistence on touching the water didn’t make her...
Continue Reading...
Riding the Waves
Youth Program
One of the first days of Swim Sail Science! (SSS), I had a kid named Simon in my boat. He was wicked quiet and didn't seem too excited about sailing. That particular day, we were going out to the airport. The wind was pretty heavy and soon Simon wasn't feeling it anymore and became sea sic...
Continue Reading...
More than a Sailing School
Youth Program
At Courageous, not every child wants to learn how to sail, but every child is given an opportunity to grow. One particular 9 year old, Maddox, is not as interested in learning how to sail. But he loves to be on boats, particularly standing on the bow of a Rhodes 19 and feeling the sea spra...
Continue Reading...

Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



Courageous Mainsail Partners


alphagraphics Triumph Modular Building americorps Parks and Rec premier capers catering peterson party center gordons wine and liquor Catering Name Tag