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Salty Dawg Caribbean Rally Celebrating 15th Anniversary. Sign Up Discounts Still Available

By George Day · On August 6, 2025

As an early supporter and volunteer for the annual Salty Dawg Caribbean Rally, it is hard for me to believe that this year will be the 15th running of America’s longest offshore cruising rally. The rally was founded by Bill and Linda Knowles, who have both passed away, but in the early days we never imagined how big it would become.

Over those one and half decades, the rally has had more than a thousand boats make the passage-in-company to the Caribbean and something like 4,000 crewmembers have taken part.  In the early years, the destination was the BVIs but for the last seven years we have sailed to Antigua, which is a more cruiser friendly island and a better launching spot for Eastern Caribbean cruising. Plus, the rally also sends a smaller fleet to the Bahamas, which is a great offshore baptism for first timers.

Skippers thinking of joining this year’s rally should be aware that August 15 is the deadline for the discounted rally fee of $450. After that the fee goes up to $500.  At either rate, the Caribbean Rally provides an enormous value for money. As of this week, the fleet is filling up rapidly. Once it reaches capacity, boats will be wait-listed.

Run by volunteers under the direction of the current association president Mike Benjamin, participants can access a long list of benefits. First, the association offers mentoring for those who are fairly new to offshore passagemaking. Sailors helping sailors is the association’s informal motto and mentoring is right at the core of that mission.

During the rally, the team provides free weather and routing for all skippers. The rally does not enforce a start date, which is usually around November 1, but does offer the advice of veteran weather guru Chris Parker who will help find just the right weather window for the departures from Hampton, Virginia and Newport, Rhode Island.

The rally also provides shore-side crews under the leadership of Tim Metcalf that provide day-to-day support and 24/7 shoreside communications for the fleet. The emergency response team has veteran blue water sailors who can offer a world of experience and facilitate a wide range of emergency responses.

In the last few years, the rally has partnered with George Washington University’s Maritime Medical Service to provide the fleet with free 24/7 telemedicine staffed by experienced emergency room physicians. Many of the doctors are also sailors.

The Salty Dawg Sailing Association is a unique and valuable sailing and cruising institution and the Caribbean Rally is its flagship event. If you are already heading to the Caribbean from the east coast this fall, I hope you will consider joining the rally.  Or, if you are still wondering if this is the year for your first long trip to the Caribbean or Bahamas, then joining the Dawgs is a no-brainer.

Either way, those who join the rally always report what a wonderful experience it is, they praise the shore teams and management and are glad to be a part of this family of cruisers. There’s even an SDSA app for your phone that allows for instant communications, a member locator map and much more.

Learn more and sign up for this fall’s Caribbean Rally here.

 

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Published by Blue Water Sailing Media, a division of Day Communications, Inc., Middletown, RI

Publisher & Editor: George Day

Blue Water Sailing Media publishes Blue Water Sailing magazine, Multihulls Today and other titles.

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George Day, Newport, RI
george@bwsailing.com
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