About Us


The Salty Dawg Sailing Association (SDSA) is a volunteer based nonprofit educational and charitable organization that conducts online webinars, live seminars, rallies and rendezvous to help sailors realize their long-distance cruising dreams. The Association strives to transfer knowledge and skills from veteran “Salty Dawgs” to less experienced cruisers, enabling independent decision-making and offshore confidence. The SDSA is a flexible close-knit collection of like-minded people with a passion for ocean sailing and the camaraderie of cruising life. The activities are made possible through the combined efforts of members, volunteers, sponsors and contributors. 

Membership in the Association is available for anyone.  SDSA offers the skills and community to expand horizons as far as your dreams will take you.  For many that participate in the Caribbean Rally to Antigua, it is just the beginning of years of cruising that may take them to the Panama Canal and around the world.   Join us today to see where your dreams will lead. 


As with all organizations, the secret to sustainability is a strong network of volunteers working together to achieve our mission, maintain our passion, and have fun. Over the last few years SDSA has greatly expanded our online education and we now host dozens of webinars on many topics, all free to our members. 

With the expansion of the Salty Dawg Rally from a couple of rallies a year  to the Salty Dawg Sailing Association means that we have built the organization from a small number of founders and volunteers  to a large contingent of enthusiastic volunteer sailors with a full schedule of educational, sailing, and social programs. We are volunteer-run and rely on the willingness of experienced cruisers to pass on their knowledge to the next generation…to pay it forward, always with an emphasis on camaraderie and fun.  Sailors helping sailors. 

As we enter our second decade, the future is bright for SDSA.  Membership continues to grow along with our greatly expanded educational offerings and activities.  Over the last few years membership has more than doubled and we have become a leading resource for blue water education and organizers of the largest offshore rally to the Caribbean from the US.   

Because of our members, event participants, volunteers, and sponsors, the Salty Dawg Sailing Association is a growing, vibrant, mission-oriented organization. You make this possible. Thank you.

—- Bob Osborn, President


Bob Osborn – President

Michael Benjamin – Vice President

Jo Ella Barnes – Secretary

Allen Roberts – Treasurer 

George Day 

Tim Metcalf 

Alex Helfand

Kathy Kubic

David McKay

Lynn Hoenke

Diane MacDonald-Mackenzie

In recognition of his contributions to the Salty Dawg Sailing Association as a Founder and President, Bill Knowles has been awarded the honorary title of President Emeritus. 

We also honored Founder Linda Knowles with a Salty Dawg tribute at her passing in 2020.  



Bob Osborn, President, Rally Director, Antigua Port Captain

Jo Ella Barnes, Corporate Filings

Allen Roberts, Treasurer

Michael Benjamin, Event Coordinator  

Katie BloxhamDawg Tales editor

Kathy Kubic, Hamptons Events Coordinator, Volunteer Coordinator

Tim Metcalf, Rally Management Team, Shoreside and Emergency Response Teams, Rally Offshore Communications

Lynn Hoenke, Communications Coordinator; articles, press releases, social media, 

Alex Helfand, Education Coordinator

Diane MacDonald-Mackenzie, Sponsor Coordinator

Tatja Hopman, Executive Director



Salty Dawgs make news.  Read it here

Salty Dawgs love SDSA.  Read it here


In the summer of 2011 Bill and Linda Knowles, cruisers from Bristol, Rhode Island, decided to explore the idea of forming a group of blue water sailors to do an informal rally from the east coast of the United States south to the British Virgin Islands.  By being part of a rally there would be boats nearby at the start and the finish, and land-based support as needed.  That first rally, in the fall of 2011, included 33 boats who had heard about the rally through word-of-mouth.   And when it was time to return to The States in the spring, fifteen boats gathered for the first Salty Dawg Spring Rally.  

Bill and Linda’s goal was to provide education and assistance to sailors who wished to gain blue water sailing experience at an affordable price.  Even today, through the help of sponsors and volunteer workers, the association keeps the rally and event costs low.  Fundamental to the group, now known as the Salty Dawg Sailing Association, is encouraging skippers to follow best practices while making their own decisions on routing and timing for heading offshore.  

Since 2011 the organization, initially known as the Salty Dawg Rally, has added Rendezvous events, meet-up among cruisers, in locations far and near; Dominica, Antigua, and Tortola as well as Virginia, Rhode Island, Maine, and Maryland.  They have also added a rally to Cuba and summer rallies to Maine and Nova Scotia.   

As years the passed, The Salty Dawgs have become a lifeline to offshore sailors as exemplified by theIr 2020 efforts.  In the spring of 2020, as islands and countries were shuttering their ports and closing their borders, SDSA organized the Homeward Bound Flotilla to help any cruiser get to the United States and safety.  Over two dozen volunteers guided nearly 200 boats back in what is believed to be the largest exodus of cruisers ever organized.  At a time when most boating events were canceled, the Salty Dawg Fall Rally was held with success in spite of the Covid-19 pandemic.  Fifty boats prepared and moved safely to ports south.  While most of the boats headed to Antigua, others went to the Bahamas or even Key West.  The Rally came off without a hitch, guiding nearly 200 sailors (captains and crew) safely to their destinations.  

2021 marks the tenth anniversary of what quickly became the largest offshore rally to the Caribbean from the US.   All along a hallmark of the rally has been a focus on education while connecting experienced skippers with those who are interested in gaining offshore sailing experience.



  • 2011: First Salty Dawg Fall Rally to the Caribbean
  • 2012: First Salty Dawg Spring Rally to the US
  • 2012: First Salty Dawg Rendezvous – Annapolis Boat Show
  • 2012: Formation of the Salty Dawg Rally as a 501(c)(3) nonprofit educational and charitable organization (The Salty Dawg Rally, dba Salty Dawg Sailing Organization, EIN: 46-1339267)
  • 2012: Formation of the First Salty Dawg Rally Board of Directors
  • 2013: First Annapolis Seminar for Long Distance passage makers
  • 2016: First Salty Dawg Rally to Maine
  • 2016: Formation of the Salty Dawg Sailing Association
  • 2017: First Salty Dawg Rally to Cuba
  • 2018: First Salty Dawg Rally to Nova Scotia
  • 2020: Homeward Bound Flotilla to bring cruisers to the USA during the CovId pandemic
  • 2021 First DelMarVa Rally


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