My wife was, at best, lukewarm about my plans. Less than a year earlier, we’d purchased our first boat, a 20-year-old Hallberg-Rassy 43, to explore the Chesapeake Bay. The idea was that after a season or two, and following retirement, we’d embark on more ambitious adventures. When the 2024 Salty Dawg Caribbean Rally from the Chesapeake to Antigua came around, I figured it was time to aim a bit farther than the local ports. “Have fun,” she told me as I joined a four-man crew on a 48-foot Leopard catamaran for the 1,700-nautical-mile passage.
For those not familiar with this event, it is a large organized flotilla of boats that depart from the U.S. East Coast each fall. Hosted by the Salty Dawg Sailing Association (SDSA), sailors cruise together to the Caribbean, with most heading to Antigua and some choosing the Bahamas as their destination. It’s considered one of the biggest and most fun rallies for cruising to those islands.
Little did we know that I’d be on the crew to finish first among more than 100 participating boats in the rally.
Not that it was a race, mind you. Or that we actually did try to win it.
How did I get on that plum crew? I submitted a resume on the Salty Dawg website. My background included my time as a midshipman, with my longest offshore sailing passage in 1979, when I competed in the Transatlantic and Fastnet Races aboard the Naval Academy’s 54-foot sloop Alliance. In the four decades since, my U.S. Navy career had provided many thousands of miles of experience navigating and commanding submarines. After retiring, I’d volunteered as a coach with the Naval Academy’s Offshore Sail Training Squadron, skippering Navy 44s from Annapolis to New England. In between, I chartered sailboats for cruises with family and friends in the Bahamas, Caribbean and San Juan Islands.
For the Salty Dawg adventure, I arrived at Safe Harbor Bluewater in Hampton, Virginia, to meet my crewmates a few days before we were scheduled to cast off on November 1. One was a retired lawyer with a lifetime of sailing experience and two lifetimes of sea stories. Another was an entrepreneur with a knack for figuring out smart solutions on board the boat. Our skipper organized a schedule of three-hour watches, and we did safety briefings, reviewed weather forecasts and provisioned.
Based on advice from Chris Parker, founder of Marine Weather Center, we left a day early and set a course to continue east beyond Bermuda, to avoid a developing low-pressure system in the Caribbean and position our boat to take advantage of prevailing easterly trade winds farther south. Conditions were ideal when we set off from the dock: 60 degrees Fahrenheit, a light southwesterly wind and unthreatening clouds. We motored to clear the Chesapeake Bay Bridge-Tunnel and then flew the asymmetrical spinnaker on a starboard tack in southwesterly winds. A broad reach propelled us past Cape Henry into the open Atlantic.
Amid a series of wind and sail changes, we averaged more than 7 knots speed over ground before entering the Gulf Stream—encouraging performance for what the owner calls his “condo-maran.” The navigation lights of a few fellow rally participants were visible nearby, but only a few.
Those first 24 hours, we logged 179 nautical miles, a good opening day, but the weather turned sporty as we pushed farther offshore. Winds built to 20 to 25 knots with waves at 6 to 10 feet. The night passages were demanding. Waves occasionally slammed the bridgedeck. And we had equipment issues. The generator wouldn’t start. Navigation sidelights were intermittent. We sailed with the anchor light during the night until we had steadier seas so we could make repairs.
According to the Salty Dawg tracker, we were on the trailing edge of the lead group of boats participating in the rally. Yes, I know—it’s not a race—but we tweaked the barber hauler just the same.
When we were 500 miles east of Cape Henry and approaching 100 miles northwest of Bermuda, Parker was still recommending that we get east. We trimmed in and found a sweet spot, making 8 knots with sustained winds in the mid-20s. Our most seasoned sailor looked up from his Starlink-connected iPhone and said: “Every other boat is either in Bermuda or heading to Bermuda.”
We could’ve diverted to join them in the harbor at St George’s if we wanted to turn back and sail at least eight hours in building conditions. Instead, we pressed east, adding second reefs in the main and genoa for the night watch.
Gusts topped 30 knots as the seas grew confused. We double-reefed both sails to control boat speed, and snugged the preventer to minimize the boom lurching between 10-foot waves. It was my first dark and stormy night on a catamaran—thankfully, nothing like the Fastnet Race of 1979 when the Irish Sea unleashed a Force 10 fury on Alliance and our 300 fellow yacht racers. Here off Bermuda, the catamaran’s two hulls seemed asynchronous in the pitching waves. Trying to sleep in a forward berth was like tumbling in a clothes dryer. I caught a nap in the athwartship settee in the salon.
By day five, we were 150 nautical miles east of Bermuda. Parker advised us not to get ahead of the pace he had outlined. We interpreted this to mean “proceed with controlled boatspeed,” so we kept the two reefs in night and day.
When it got to be dawn on day seven, we were on schedule to arrive too early, with the potential for driving into significant wind and waves. We improved our position and were happy to find good conditions as we set a rhumb line course for Antigua, 30 miles ahead and 50 miles east of the rally’s lead pack of boats. Most of them had stopped in Bermuda, but also had advantages in design, waterline length and sails that could help them overtake us. We again reminded ourselves that it’s not a race, as we tasted the chance for victory.
In the darkness of my last midwatch, I tried to coax some speed in lighter winds when the breeze built suddenly to 19 knots, then high 20s, then gusts to 34. We were running under full main and genoa as rain pelted the helm roof. I furled the genoa to storm jib size. At least I hoped I had. It was too dark to see the foredeck, and I was too busy to grab the lantern to check.
The boat handled it, and the squall subsided as quickly as it had sprung. I kicked myself for not seeing this coming, even with an active scan on radar. Where were the red and yellow returns we had detected on the radar plot in numerous previous squalls? We learned later that radar gains had been adjusted earlier in the day, reducing the sensitivity for detecting rain squalls.
But hey, I was on board to learn, right?
It turned out to be our last squall of the rally. With 1,300 miles in our wake, the weather continued to moderate as we close-reached toward English Harbour on the southern coast of Antigua. Now in the homestretch, we were 30 miles ahead of the next boat, a semi-custom Balance 526 catamaran. It had narrowed the gap on us since leaving Bermuda, making 9 knots in 12 knots of true wind. We trimmed for speed.
Dawn broke on our final day at sea. Approaching Barbuda, Antigua’s island neighbor to the north, we were treated to a pod of dolphins playing in our bows. Being on the ocean with these beautiful animals never gets old. By noon, we could see the peaks of Antigua on the horizon. Earlier, we had passed within 15 miles of low-lying Barbuda without seeing anything, so Antigua was the first land we’d seen in 10 days. It gave us all a second wind.
In the final hours of our passage, the gentle 12-knot breeze eased to 10 knots, then 8, then 3. There was open ocean between us and Africa, and yet the restless sea was calm. A check of the rally map showed us ahead of all the other boats. The Balance 526 was motoring hard and getting closer every hour. Our wind was down to 3 knots, so we started our engines too, and motored along Antigua’s east coast. When we were near Half Moon Bay, we tried one final spinnaker set, but the wind was too light and variable. So, we doused the asymmetrical for the final time and stowed it away.
We passed below Shirley Heights and cleared Charlotte Point to enter English Harbour. Fort Berkeley stood guard as we navigated into the calm, protected harbor, a cool blend of island and England. We did a quick survey of available anchorages and approached the wharf at Nelson’s Dockyard.
A small welcoming committee of Salty Dawg officials attended our landing, and took our mooring line to a dockside cleat. We had arrived 10 days, eight hours and 1,749 nautical miles after departing Little Creek in Virginia.
With appropriate (meaning zero) fanfare, the rally director toasted us with a tot of rum as “first to finish,” ending with the now familiar refrain: “Remember, it’s not a race.”
Yes, we agreed, that’s true. But let’s celebrate anyway.
March 2025
