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Cruising to the Caribbean wasn’t at the top or even on Jennifer and Adam Landa’s bucket list. Now, they’re glad they made the leap. In November 2022, the Landas boarded their Fountaine Pajor Saona 47, Solmate, cast off from Hampton, VA, as one of 70 boats bound for the island of Antigua in the Salty Dawg Sailing Association’s (SDSA) Fall Caribbean Rally.
“Our adventure sport was motorcycles. We’ve traveled and motorcycled on five continents,” says Jennifer Landa, a physi- cian from Yonkers, NY. “The only sailing we did was charter a bareboat in the British Virgin Islands a couple times. My husband had sailed as a teenager. That last charter was in March 2020. The island’s border closed due to COVID-19, and we had the BVIs to ourselves for a couple of days before we got the last flight out.”
One of those days, I looked at my husband and said, ‘We could just stay.’ He didn’t answer. My thought was we could work virtually, and by then, we were empty nesters. When we got home, we watched every YouTube video of couples living aboard. Five months later, my husband agreed and answered, ‘Yes, we could.’ ”
The Landa’s sold their house and cars, bought the boat and lived in a marina in Fort Lauderdale for four months. Over the next two years, they gained experience sailing from Florida to the Chesapeake and wintered six months in the Bahamas. The couple planned to sail Solmate to Brunswick, GA, store her there, and travel by land to see friends and family. Instead, in a snap decision made after a year of serious pondering, the Landa’s kept sailing to Hampton for the departure of the SDSA’s Fall Caribbean Rally.
“The Caribbean Rally really opened up a whole new world for us,” says Landa.
Sailing rallies to the Caribbean aren’t new. The first, the Atlantic Rally for Cruisers (ARC), celebrates 40 years this year. It’s run by the U.K.-based World Cruising Club (WCC) with a fleet of nearly 300 boats annually departing from the Canary Islands to St. Lucia. On this side of the pond, Steve Black launched his Caribbean 1500 cruising rally in 1990 with 50 boats passage-making from Hampton, VA, to Virgin Gorda, BVI. The popularity of cruising-in-company caught on.
In 2011, veteran cruisers Bill and Linda Knowles and their Jack Russel terrier, Brie, started the Salty Dawg Rally to the Caribbean. The SDSA has grown into a nonprofit hosting education events and rallies year-round. The annual Fall Carib- bean Rally is now the largest organized flotilla of cruisers leaving the U.S. East Coast for the Caribbean.
“The SDSA’s educational mission is for experienced offshore passage-makers to share their knowledge with those who wish to learn more about the sport and the adventure it presents. We do this through webinars, short rallies during the summer off the U.S. East Coast, seminars and social activities before and after rallies, and more recently, WhatsApp groups that let “Dawgs” stay in touch whether it’s to meet up for dinner or get recom- mendations for repair work,” says Bob Osborn, the SDSA’s president, who with wife Brenda have cruised their Aerodyne 47, Pandora, since 2012.
To enter the Fall Caribbean Rally costs $450 per boat. One of the benefits of rallying is that the entry fee offers a package deal on services that individuals sailing solo would need to purchase a la carte, Osborn says. This includes customized weather briefings and routing suggestions by the Marine Weather Center before departure and daily offshore weather updates via email and SSB while underway.
There’s also position tracking by PredictWind, where friends, family, the SDSA Shoreside Coordinator team, and the U.S. Coast Guard can see a vessel’s live positions. New this year, ralliers can access 24/7 emergency medical support by George Washington Maritime Medical Services.
The availability of Starlink has been a game changer for those who wrestle with when to cruise to the Caribbean: now or when they retire, says Kathy Kubic, from Charleston, SC, who, with her husband, has sailed in the SDSA Fall Caribbean Rally on their Leopard 45, Island Time, for six years. “When the kids went to college, we sold the house, bought a boat, and lived in a marina in Annapolis. We always wanted to cut the lines. One day, we met this gentleman at the marina who said there’s no need to ‘do it in order,’ meaning work then cruise. With Starlink, we’ve been able to work and cruise.”
Some 20% of the boats that contact SDSA about the Caribbean Rally aren’t ready, says Osborn. “One of the first things we tell them is to get overnight experience. Our DelMarVa Rally in June is a wonderful way to do this. It’s a week-long, 450-mile counter-clockwise sail around Delmarva Peninsula. The Downeast Rally in July is a sail from Hampton to Newport with an optional mini cruise around Maine. Or, if someone doesn’t have time, I recommend they pick a good weather window, sail out into the Atlantic for two days, and come back. It’s a cruise to nowhere, but you don’t know what you don’t know until you do it. For example, what is it like to reef your sail at 2:00 a.m. or navigate at night? Or get sleep onboard so you’re rested for watches? After all, we don’t want someone’s first trip to be their only one.”
Cindy Petelinkar was ready when she sailed her 48’ Oceanis, Luffin’ Life, to Antigua on the SDSA Fall Caribbean Rally. The Horsham Township, PA, resident first learned about SDSA’s Caribbean Rally via the organization’s tent at the Annapolis Boat Show. At the time, Petelinkar considered it a far-reaching dream.
The following year, she signed up to crew for friends in the DelMarVa and Downeast Rallies. Friends she met in these mini-rallies invited her to crew for them in the World ARC, the WCC’s round-the-world rally, on the leg from Namibia, in southern Africa, to Salvador, Brazil. Last year, Petelinkar felt ready to captain her boat in the rally.
“At that stage, I had the boat ready, all the safety equipment on board, and, more importantly, I knew how to use it. One of the most important pieces in preparation is to pick the right crew. There’s an art to picking crew. Tell them what you expect of them upfront. Sailing knowledge is good, but it isn’t everything. I’d rather have a trauma nurse or helicopter mechanic onboard than someone who tells me they’ve completed X number of sailing courses.”
The sail from Hampton, VA, to Falmouth Harbour, Antigua, averages 10 to 12 days. It’s common to sail the whole way without seeing another rally boat.
“Good food and trying to gather together for one meal a day helps pass the time,” says Island Time’s Kubic. “Crossing the Gulf Stream in the early part of the trip, and the chance of seasickness if the water is like a washing machine, means it’s important to have meals and snacks that are easy to manage. This means frozen one-bowl meals that you can make before the trip. Also, protein or granola bars.”
Go fishing, suggests Luffin’ Life’s Petelinkar. “There’s nothing more exciting than yelling ‘fish on.’ Besides that, if there’s no wind, we may stop for a swim. Everyone wants to see the green flash, so sunset is a highlight. We play cards, read books, star gaze or play a movie we downloaded before the trip.”
The arrival of nearly 100 boats and crews before Thanksgiving helps Antigua kick off its tourism season early. Welcome parties, group hikes, beach trips and other social events are scheduled for the first week or two after arrival. After that, some leave their boats in Antigua, and fly to the United States and back to cruise over winter holidays.
Others cast off on an extended winter season cruise before sailing north in the spring. Last year, the SDSA put together a series of informal rendezvous. To the north, this includes Dominica in February, the BVI in March, and the Dominican Republic in April, while to the South, there’s the Martinique Carnival in February and Bequia in March or April for its Easter Regatta.
“We call it a menu of opportunities,” says Kubic, of the SDSA’s activities planned in Antigua and rendezvous during the season. “Cruisers are fiercely independent, so there is no requirement to do any of these or all. The opportunities, though, are a nice chance to meet up, share experiences and recommendations with new and old friends, and enjoy the island destination. That’s what being part of a cruising rally is all about.”
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