SDSA Caribbean Rally

2021 Tracking Map

November 1 departure (weather permitting)


Fees & What's Included

Passage Discussion
Required Equipment
Pre-departure Activities
Antigua Arrival Activities
Crew Service
Predict Wind
Rally FAQs
Volunteer to Help

The largest rally leaving the US East Coast each fall is the Caribbean Rally hosted by the Salty Dawg Sailing Association, the fleet departs from Hampton VA, at the mouth of the Chesapeake Bay to head offshore to points south.  

It is not only the largest organized flotilla of cruisers leaving the US East Coast for the Caribbean—but the most fun.  The Caribbean Rally helps sailors arrive safely in the Caribbean and opens the door to new lifelong friends and experiences while cruising.

Where will you head this fall?  The Caribbean Rally provides you a choice of destinations. While the bulk of the fleet heads to Antigua, some choose to make landfall in the Abacos in the Bahamas. Whatever your destination, you will have the full support of SDSA either way.  If you’re considering cruising the Caribbean, read this article by Bob Osborn, Rally Director, A Case for Making Landfall in Antigua.

 Not sure if you are ready to participate in the Caribbean Rally? Watch the recording of the zoom briefing on Cruising in the Time of Covid, September 22, 5pm ET. Watch here.


Bob also gave a recent presentation about what is like to visit Antigua and cruise the islands south to Grenada, the southern portion of the Lesser Antilles.


The modest rally fee includes weather routing by Chris Parker of the Marine Weather Center, position tracking by PredictWind, and an extensive level of coordination and support from our shoreside team during the offshore passage.  Once accepted into the rally and rally fees are paid, you will have access to  extensive  information to help you prepare for a safe passage, including information about your destination and arrival plans. 

This recently recorded presentation by Bob Osborn, Rally Director and Bennett Kashdan, SDSA board of directors, is an overview of how plans are developing as it relates to safety given the risks that the Delta Covid variant and what cruising might look like in the islands this winter.  They also reviewed passage considerations and a preview of arrival events in Antigua. Watch here.

Thinking of heading to the Bahamas? Watch our Caribbean Rally Briefing  - Focus on the Bahamas

Questions?  Need more information?  Reach out to Bob Osborn, Rally Director, at [email protected] or for Bahamas specific questions contact Allen Roberts, Bahamas Port Captain, at [email protected].

Events begin on October 28 in Hampton, VA for final boat and crew preparation, seminars, social events and weather briefings. 

A highlight of these events will be a live Search and Rescue (SAR) with a USCG J-Hawk helicopter, right out in front of the Marina where our events are to be held.   It is an amazing experience to see and hear this display, a spectacle that you will not soon forget.


Departure is scheduled for Nov 1, weather permitting.  Each Captain is expected to make the best decision for his crew and boat when picking a departure date.  Passage time for boats headed to the Bahamas averages 4-6 days, and the boats traveling the 1400 NM to Antigua generally arrive in 10-14 days.

Both VHF radio and offshore communications equipment are required.

Don't forget to stay in touch with the Salty Dawgs on Facebook; Salty Dawg Sailing and Friends


Rally participants, both skippers and crew will also have the opportunity to participate in a dedicated rally forum where questions and plans can be shared with other rally participants and experts. Details are available to registered boats and crew. 


The SDSA unites experienced ocean sailors with developing cruisers to broaden their blue water horizons.  All Salty Dawg rallies and events are led by seasoned sailors who volunteer their time and knowledge to help cruisers realize their dreams.


2021 Caribbean Rally Participant List


All Salty Dawg rallies and events are led by seasoned sailors who volunteer their time and knowledge to help cruisers realize their dreams.   If you would like to join us as a volunteer, we would love to benefit from your passion, personality, and expertise as we plan future events.  Contact Us to Volunteer.


Helpful Links

Sailing with Kids 
Sailing with Pets

COVID-19 and the 2021 Fall Caribbean Rally:   "Safety and Participation"

As the COVID-19 pandemic evolves, the SDSA will continue to explore the best ways to conduct its 2021 activities in as safe and enjoyable a manner as possible. Read More

Heading south?  The Dawgs will be waiting for you.