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If there’s one thing cruising sailors are good at, it’s going with the flow. When weather, gear failure or some other difficulty shuts down one carefully planned course of action, an experienced cruiser never bats an eye. He or she just plots a new course and carries on regardless. It’s why we write out “Point A bound for Point B” when logging a passage because we never can be sure where we’ll land.

The flow in the Caribbean this past spring was decidedly turbulent as Covid-19 lockdowns swept through the region. The regular cruising season abruptly ended in March, as all islands, with the sole exception of the U.S. Virgins, stopped receiving visitors, and hundreds of skippers were left puzzling over how to get their boats back to the United States. Many found themselves shorthanded, as crews scheduled to fly in for the long haul home suddenly couldn’t join their boats. Others with boats based permanently in the Caribbean that are normally stored on southern islands like Trinidad during hurricane season faced the prospect of long offshore passages they felt unprepared for.

Into this awful breach stepped a very cruiserly organization, the Salty Dawg Sailing Association (, which has for years run rallies, shepherding groups of boats back and forth to the Caribbean each spring and fall. Early on the Salty Dawgs saw that their regular spring rally out of the British Virgins, which normally attracts about 30 boats, couldn’t come off as planned. Instead of just cancelling it, though, they decided instead to blow it up and make it even bigger.

The Dawgs spread the word via social media: they waived their regular entry fee, deleted their equipment and competency requirements and announced to the Caribbean cruising world that anyone who wanted to could join for free and start from anywhere in what was now termed the “Homeward Bound Flotilla.” A total of 252 boats registered, and in the end, 184 took part, setting out from various locations across the Eastern Caribbean on five successive Sundays, plus one Wednesday, in April and May.

It was a stupendous effort. A team of 22 Dawgs plus their regular weather-router, Chris Parker of Maine Weather Center (, supported the six waves of boats, which taken together constituted the largest organized group ever to sail between the Caribbean and United States, as they followed various routes home through two tropical storms and one nasty trough.

PredictWind ( also stepped up, providing free tracking services, so the Dawgs could keep tabs on their fleet. Prior to each departure date, a team of vessel-tracking coordinators worked with the skippers to ensure they could successfully plug into the system. Boats lacking the technology to do so were assigned buddy boats that could keep them in the loop via VHF. Less experienced skippers with less well-equipped boats were also assigned buddies. While boats were en route, shoreside coordinators maintained contact with and verified the status and position of each flotilla member, in the process fielding about 100 queries a day. Expert emergency response teams helped skippers troubleshoot any special problems they may have encountered.

To top it off, SDSA president Hank George also led a team that maintained constant communications with the governments of the United State, the Bahamas, Bermuda and a number of other islands in order keep their flotilla members fully informed on the ever-fluctuating emergency prescriptions and regulations being issued across the region.

As part of this effort, the Dawgs even succeeded in convincing the Bahamians, who’d originally banned all boats from their waters under threat of a $10,000 fine, to let flotilla members stop there if necessary. This was critical, as in the end most flotilla members routed through or around the Bahamas, and almost 100 boats ended up taking advantage of the special exception the Dawgs had carved out for them.

“The biggest measure of our success is the volume of unsolicited thank you notes we got,” George says. “That’s how we know we did good.”

Looking ahead, a question mark continues to hang over the next Caribbean cruising season. Will sailors take their chances visiting the islands? Will the islands take their chances to let boats visit? It remains to be seen. For now, though, we can all tip our hats to the Salty Dawgs, as they proved once again that cruisers not only go with the flow, they also take care of each other.

July/August 2020 



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