A cruising couple signs on for a Salty Dawg Rally to the Caribbean

By Jim Bradley

Azure blue skies, steady trade winds, white sand beaches, rum drinks, watching the Caribbean sun sink into the sea – these were on our mind as we thought of bringing our Shannon 47/52 sailboat Kalli to the Caribbean after a summer of sailing in the Northeast. Weather bombs, dismastings, mechanical problems, spare boat parts – these were also very much on our minds as we thought about the daunting 1,500-mile offshore sail to get Kalli to the islands of the Caribbean.


Kalli at anchor

We are a couple in our early sixties and have spent a lifetime sailing – but like many sailors the demands of our jobs and raising two children meant sailing limited to weekends, two-week vacations on the boat, and charters in the Caribbean. We had experience enough to know that we wanted to try the ‘liveaboard’ lifestyle – but we also knew we lacked serious offshore credentials. We were confident in the boat and in our knowledge base. We spent decades reading the words of wisdom from the masters – the Pardees, John Kretschmer, heavy weather sailing books, and the monthly sailing journals. But we lacked in the doing it – not just reading about it – offshore experience.

Our preparations started years before our departure. The boat was built in 1999; we bought her in 2013. We replaced our standing rigging and turnbuckles, repowered with a Yanmar diesel engine, retiring the more than two-decade-old Westerbeke, and added solar panels, a wind generator and Firefly carbon foam batteries. We added a full bimini to shield us from the Caribbean sun – with side panels. We didn’t appreciate the value of the side panels until our offshore sail to Antigua. We had Carol Hasse of Port Townsend Sails make new sails for Kalli, with triple reef points in the mainsail. The boat was ready…but were we?

For many reasons, the thought of joining a rally to the Caribbean was appealing. We signed up with the Salty Dawg Rally to Antigua, departing Hampton, Virginia in early November. First of all, COVID had complicated travel and the Salty Dawg Sailing Association did an excellent job interacting directly with the Antigua government to allow the Salty Dawg boats to seamlessly enter Antigua. All the Salty Dawgs had a negative COVID test upon departing Hampton, and Antigua allowed our time at sea to count toward quarantine.

Beginning several weeks before departure, a number of Zoom meetings were arranged in lieu of the usual in-person seminars on weather, safety, provisioning and heavy weather tactics. One Zoom presentation by the Coast Guard was especially memorable – the Coast Guard officer showed slides of the type of boats (110-foot cutter) that would rescue us if we got into serious trouble and the Sikorsky MH60T helicopter that would airlift us off the boat in an extreme emergency. His words echoed in my mind: “If you call us we will come out to get you!” We hoped it would not be us that had to call.

The level of support was impressive. Each boat was tracked by the Salty Dawg shoreside crew and Coast Guard by Iridium Go Predict Wind satellite tracking, with backup tracking on the Garmin InReach. We received daily email updates before departure from Sheldon Stuchell, our rally coordinator. Chris Parker’s weather and routing services were included in the rally fee and Chris did a number of presentations on weather and routing strategies the week before sailing from Hampton. He advised the Salty Dawg group on the best departure weather window and provided GPS waypoints to deal with the Gulf Stream currents and eddies. We received daily weather updates and strategy suggestions from Chris Parker via Iridium Go email. The most important GPS coordinate was the point that we had made enough easting to finally catch the trade winds and turn southeast on a rhumbline toward Antigua. We left Hampton on a northeast course to take advantage of the Gulf Stream current to take us east (My wife Arden, pointing southeast – “ Wait. Isn’t Antigua THAT way? )

Three weeks before leaving Hampton, we got an unsettling phone call. Our longtime friend and planned third crew member John was to join us for the sail. He began losing strength and muscle in his hands and was diagnosed with a nerve entrapment that would require immediate surgery at both elbows. “So I am out.” There were a few couples and even a singlehander planning to do the rally, but we had mentally prepared for a five-to six-hour off watch rest for the ten- to twelve-day trip.

We had met Mark, a sailor who had come by the boat to introduce himself in Stonington, CT over the summer. He was surprised to hear from us and even more surprised to be invited on an all expense paid sailing trip with us to Antigua in just two weeks. Thankfully, he was free and said he could join us. We knew he had sailing experience, but we didn’t realize the depth of his experience until he was aboard and shared some of his sailing stories. “That time I circumnavigated Africa” and the “third Atlantic passage” and “the time I crossed the Pacific with my girlfriend”. Having Mark aboard neutralized some of our fears and inexperience. Most boats in the rally had crew – mostly friends, others supplied by a crew list provided by the Salty Dawg Rally and crew finder websites on the Internet.


Swing time before a lobster dinner on Barbuda


The day finally arrived for departure from Blue Water Marina in Hampton. The thirty or so boats headed to Antigua left the docks at 6 am in 20 knots of a west wind. A few boats had left a day early – departure recommendations were suggestions – we repeatedly got the message that the ultimate decision making was up to the captain of each boat. We left the Chesapeake Bay Bridge behind and were out into the Atlantic – we were on our way.

I wouldn’t call the passage easy, but we didn’t have other offshore passages to compare. We were close hauled for seven or eight days once on a rhumbline for Antigua. We were on a heel on port tack with the starboard rail near the water for much of the trip, with a double-reefed mainsail and reefed Yankee cut jib with apparent wind of mostly 20 to 26 knots and 10- to 15-foot seas. Spray and water over the deck were common and many boats (including Kalli) discovered deck leaks we didn’t know we had.

The side panels on the bimini were a blessing and saved us from salty drenchings. Occasional squalls would bring wind speeds into the thirties, but Kalli handled them well by easing the mainsheet and traveler and changing briefly to a more downwind course. There was a mix of experience in the rally – many boats had done this passage before. They felt this was one of the more difficult passages compared to previous years given the close reach conditions, but none felt the conditions were highly unusual. Our ability to point relatively high (compared to other boats in the rally – catamarans made up approximately 50%) put us in the first third of the group arriving Antigua.

I heard the cry of “Land Ho!” from my off-watch bunk. We rounded Barbuda early in the morning of our tenth day of sailing from Hampton, VA to English Harbour, Antigua. The wind was delightfully from the beam after days and days of close reaching. We had been sailing within eyesight of Salty Dawg boats Flora (a Hallberg-Rassy) and Tropicool for days. The catamaran Tropicool liked the beam reach conditions and quickly pulled away from us. We had a feeling of accomplishment as we furled the sails outside Fort Berkeley of English Harbour and dropped anchor in Freemans Bay. After clearing customs, we med moored Kalli at Nelson’s Dockyard without mayhem. Tradition dictates that the first boat in host a party, and Iain on Fatjax (a Shipman 63) did not disappoint. He introduced us to Antigua rum punch with generous (very generous) servings! We spent the next several days exploring English Harbor and comparing stories of our passage with our new Salty Dawg friends.


Enjoying cold ones at a street pub on Dominica


For us, the friendships and camaraderie were the best part of joining the Salty Dawg Rally. We had countless sundowners with other sailors, discussing boat problems and future sailing plans. We sailed to Barbuda and Dominica in the company of other Salty Dawg boats and had others introduce themselves in harbors when they spotted our Salty Dawg burgee.

Like many cruisers, the worldwide COVID crisis led to a change of plans. Our dream of crossing the Pacific to New Zealand has been placed on hold, so we plan to explore the coast of Maine this summer. Which means you will likely see us traveling back to the Caribbean with the Salty Dawgs next November. Look for us on Kalli and come over to say hello. We are the blue Shannon flying the Salty Dawg burgee. ■

Arden & Jim Bradley’s homeport is Stuart FL, although they’ve been living aboard Kalli for over a year.  

Salty Dawg Rallies (to and from the Caribbean as well as Bermuda, Downeast Maine, the Canadian Maritimes and more) are conducted by the Salty Dawg Sailing Association (SDSA), an educational and charitable organization with a mission to educate sailors, build camaraderie, and facilitate offshore passages. 

Celebrating ten years of sailors helping sailors, the volunteer-led SDSA was founded on the principle of transferring knowledge and skills from veteran “Dawgs” to less experienced sailors, enabling independent decision-making and building offshore confidence. You are cordially invited to join the fun at saltydawgsailing.org.