The Salty Dawg Fall Rally to the Caribbean is ON! PDF Print Email
Thursday, August 06, 2020 12:00 AM

Hampton, VA (USA) - 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 Caribbean Rally. Are you onboard? 

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

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 may 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 Caribbean 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.

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 SSB equipped 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!

Hosting blue water rallies in the U.S. and Caribbean is one of our specialties. Each rally is an opportunity for sailors to cruise-in-company, with the safety, camaraderie, and passage-preparation assistance that a rally can provide. Meet new friends and re-unite with old ones. Kids and pets are welcome.

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. Independent thinkers value the Salty Dawg focus on the importance of each skipper’s role to make the right decisions for his or her boat and crew.