Salty Dawg Fall Rally to the Caribbean 2020

The fall rally to the Caribbean is on!
A picture-perfect sunset on the beach in Dominica Courtesy of Salty Dawg Sailing Association

It’s time to make your plan to join the largest rally from the U.S. to the Caribbean. Discover paradise. Make new friends. Experience a season in the warm and beautiful Caribbean.

Countdown has begun for the Salty Dawg Sailing Association’s Fall Rally to the Caribbean. Are you onboard? Click here to find out more.

The Fall Rally to the Caribbean will be heading to beautiful Falmouth Harbour, Antigua. And, if things ease up in the Bahamas, there will be boats making landfall in gorgeous Harbour Island, Eleuthera.

2019 rally fleet
The 2019 rally fleet tied up at Nelson’s Dockyard, Antigua. Salty Dawg Sailing Association

Departure is scheduled for Nov. 2 (weather permitting) from the Chesapeake Bay. Prior to departure, veteran Salty Dawgs will be ready and willing to help with passage preparations. With COVID-19 concerns our social activities will be limited. We’ll be conducting webinars in lieu of in-person seminars and Zoom Meetings in lieu of in-person general meetings and Q&A sessions.

Like our recent Homeward Bound Flotilla, we will have a Government Support Unit, a first for our Fall Rally, to keep organizers and participants up to date on changing restrictions at departure and arrival locations.

Once underway, our PredictWind-sponsored “Follow the Fleet” tracking system will follow your progress based on the position reports you send either electronically or by radio. Friends, family, and armchair sailors can follow your track.

2019 Salty Dawg Fall Rally
Kids from the 2019 Salty Dawg Fall Rally fleet. Salty Dawg Sailing Association

Each Captain receives daily weather updates by email from Chris Parker at Marine Weather Center and can access personalized weather routing suggestions, if needed. Daily SSB radio nets keep boats in contact with each other, sharing tales of offshore problem-solving and fishing success. In addition, our Shoreside Team monitors your progress and becomes an important element of our response in case of emergency.


  • Education: Pre-departure webinars with experts and vendors. Learn how to prepare and what to expect on your passage to the Caribbean.
  • Safety: Pre-departure expert advice, professional weather routing before and during passage, daily fleet tracking and check-ins, daily social radio hour, Fleet Safety Net, USCG monitoring.
  • Networking: Network with other participating sailors. Learn and share information. Build lifetime friendships with traveling buddies.
  • Resources: A staff of “like sailors” who support you from pre-departure thru post-passage. Extensive network of offshore cruisers. Expert information from product manufacturers. Discounts on slips and moorings, marine products and services. Fleet tracker for family and friends. Crew List Service.
  • Flexibility: We provide the resources, information and advice to help you realize your sailing dream, but you maintain the flexibility to make your own decisions.

Salty Dawg burgees are found on vessels around the world. Between 2011 and 2020 the SDSA has put on 30 rallies with 3,800 sailors participating on 1,350 boats. Over 3,200 sailors subscribe to our bi-monthly newsletter, Dawg Tales. Membership in the Association is available to anyone interested in passage making or long-distance cruising. We’d love to have you join us!

Click here to find out more about the 2020 Fall Rally to the Caribbean.


Click here to register.